Log in

Relevant bibliographies by topics / Cyanohydrine / Journal articles

To see the other types of publications on this topic, follow the link: Cyanohydrine.

Journal articles on the topic 'Cyanohydrine'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the top 50 journal articles for your research on the topic 'Cyanohydrine.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Browse journal articles on a wide variety of disciplines and organise your bibliography correctly.

1

Effenberger, Franz, Jürgen Roos, Christoph Kobler, and Holger Bühler. "Hydroxynitrile lyase-catalyzed addition of HCN to 4-substituted cyclohexanones: stereoselective preparation of tetronic acids." Canadian Journal of Chemistry 80, no. 6 (June 1, 2002): 671–79. http://dx.doi.org/10.1139/v02-087.

Full text

Abstract:

The addition of HCN to 4-alkylcyclohexanones 1 to give cyanohydrins 2 is strongly catalyzed by hydroxy-ni trile lyases (HNLs). With PaHNL, from bitter almond, trans-addition occurs almost exclusively, yielding trans-2. With MeHNL, from cassava, cis-addition is preferred to give cis-2. cis-Selectivity is nearly quantitative, especially for cyclohexanones with larger 4-substituents. Comparable results with respect to the stereoselectivity were observed in the HNL-catalyzed addition of HCN to 4-alkoxycyclohexanones 3ag. In contrast, the stereoselectivity in the HNL-catalyzed addition to 4-alkanoyloxycyclohexanones 3hk is very poor. The transformation of cis-4-propylcyclohexanone cyanohydrin (2c) into the corresponding cis-spirotetronic acid 7 occurs without any isomerization.Key words: enzyme, hydroxynitrile lyase, cyclohexanones, cyanohydrins, cis/trans-stereoselectivity.

APA, Harvard, Vancouver, ISO, and other styles

2

Baeza, Alejandro, José M. Sansano, José M. Saá, and Carmen Nájera. "Enantioenriched cyanohydrin O-phosphates: Synthesis and applications as chiral building blocks." Pure and Applied Chemistry 79, no. 2 (January 1, 2007): 213–21. http://dx.doi.org/10.1351/pac200779020213.

Full text

Abstract:

Aluminum complexes of the chiral (R)- or (S)-3,3'-bis(diethylaminomethyl)-1,1'-bi-2,2'-naphthol (BINOLAM) ligand behave as efficient catalysts for the enantioselective cyanation-O-functionalization of aldehydes, thereby leading to enantiomerically enriched O-silyl, O-methoxycarbonyl, or O-phosphate derivatives of cyanohydrins. The enantioenriched cyanohydrin-O-phosphates are useful for the synthesis of several enantioenriched compounds such as α-hydroxy esters, β-amino alcohols, and γ-substituted α,β-unsaturated nitriles. Natural products such as (-)-aegeline and (-)-tembamide have been prepared in this manner.

APA, Harvard, Vancouver, ISO, and other styles

3

Dvořáková, Hana, Antonín Holý, Ivan Votruba, and Milena Masojídková. "Synthesis and Biological Effects of Acyclic Analogs of Deazapurine Nucleosides." Collection of Czechoslovak Chemical Communications 58, no. 3 (1993): 629–48. http://dx.doi.org/10.1135/cccc19930629.

Full text

Abstract:

Deaza analogs of three basic types of S-adenosyl-L-homocysteine hydrolase (SAHase) inhibitors, (S)-DHPA (I), eritadenine (II) and AHPA (III), were prepared. Alkylation of 3-deazaadenine (V), 3-deazapurine (VI), 1-deazaadenine (VII) and 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (XXII) with (R)-2,2-dimethyl-4-tosyloxymethyl-1,3-dioxolane (XIIIb), followed by acid hydrolysis, afforded the corresponding (S)-2,3-dihydroxypropyl derivatives XVIIa -XIXa and XXV. Reaction of V and VII with 2,3-O-cyclohexylidene-D-erythrono lactone (XXIX) and subsequent removal of the protecting groups in an acid medium gave eritadenine analogs XXVII and XXVIII. Compounds V and VII were alkylated with bromoacetaldehyde diethyl acetal to give N-(2,2-diethoxyethyl) derivatives XXXII and XXXIII from which the substituted acetaldehyde derivatives were liberated in situ and converted into compounds XXX and XXXI by cyanohydrine reaction followed by acid hydrolysis. The alkylations were performed in dimethylformamide with sodium or cesium salts of the bases. Biological activity was observed only with 3-deazaadenine derivatives XVIIa, XXVII and XXX, which exhibit both enzyme-inhibitory and antiviral activities.

APA, Harvard, Vancouver, ISO, and other styles

4

Luque-Almagro, Victor M., Faustino Merchán, Rafael Blasco, M. Isabel Igeño, Manuel Martínez-Luque, Conrado Moreno-Vivián, Francisco Castillo, and M. Dolores Roldán. "Cyanide degradation by Pseudomonas pseudoalcaligenes CECT5344 involves a malate : quinone oxidoreductase and an associated cyanide-insensitive electron transfer chain." Microbiology 157, no. 3 (March 1, 2011): 739–46. http://dx.doi.org/10.1099/mic.0.045286-0.

Full text

Abstract:

The alkaliphilic bacterium Pseudomonas pseudoalcaligenes CECT5344 is able to grow with cyanide as the sole nitrogen source. Membrane fractions from cells grown under cyanotrophic conditions catalysed the production of oxaloacetate from l-malate. Several enzymic activities of the tricarboxylic acid and glyoxylate cycles in association with the cyanide-insensitive respiratory pathway seem to be responsible for the oxaloacetate formation in vivo. Thus, in cyanide-grown cells, citrate synthase and isocitrate lyase activities were significantly higher than those observed with other nitrogen sources. Malate dehydrogenase activity was undetectable, but a malate : quinone oxidoreductase activity coupled to the cyanide-insensitive alternative oxidase was found in membrane fractions from cyanide-grown cells. Therefore, oxaloacetate production was linked to the cyanide-insensitive respiration in P. pseudoalcaligenes CECT5344. Cyanide and oxaloacetate reacted chemically inside the cells to produce a cyanohydrin (2-hydroxynitrile), which was further converted to ammonium. In addition to cyanide, strain CECT5344 was able to grow with several cyano derivatives, such as 2- and 3-hydroxynitriles. The specific system required for uptake and metabolization of cyanohydrins was induced by cyanide and by 2-hydroxynitriles, such as the cyanohydrins of oxaloacetate and 2-oxoglutarate.

APA, Harvard, Vancouver, ISO, and other styles

5

Kunz, Daniel A., Jui-Lin Chen, and Guangliang Pan. "Accumulation of α-Keto Acids as Essential Components in Cyanide Assimilation by Pseudomonas fluorescens NCIMB 11764." Applied and Environmental Microbiology 64, no. 11 (November 1, 1998): 4452–59. http://dx.doi.org/10.1128/aem.64.11.4452-4459.1998.

Full text

Abstract:

ABSTRACT Pyruvate (Pyr) and α-ketoglutarate (αKg) accumulated when cells of Pseudomonas fluorescens NCIMB 11764 were cultivated on growth-limiting amounts of ammonia or cyanide and were shown to be responsible for the nonenzymatic removal of cyanide from culture fluids as previously reported (J.-L. Chen and D. A. Kunz, FEMS Microbiol. Lett. 156:61–67, 1997). The accumulation of keto acids in the medium paralleled the increase in cyanide-removing activity, with maximal activity (760 μmol of cyanide removed min−1 ml of culture fluid−1) being recovered after 72 h of cultivation, at which time the keto acid concentration was 23 mM. The reaction products that formed between the biologically formed keto acids and cyanide were unambiguously identified as the corresponding cyanohydrins by 13C nuclear magnetic resonance spectroscopy. Both the Pyr and α-Kg cyanohydrins were further metabolized by cell extracts and served also as nitrogenous growth substrates. Radiotracer experiments showed that CO2 (and NH3) were formed as enzymatic conversion products, with the keto acid being regenerated as a coproduct. Evidence that the enzyme responsible for cyanohydrin conversion is cyanide oxygenase, which was shown previously to be required for cyanide utilization, is based on results showing that (i) conversion occurred only when extracts were induced for the enzyme, (ii) conversion was oxygen and reduced-pyridine nucleotide dependent, and (iii) a mutant strain defective in the enzyme was unable to grow when it was provided with the cyanohydrins as a growth substrate. Pyr and αKg were further shown to protect cells from cyanide poisoning, and excretion of the two was directly linked to utilization of cyanide as a growth substrate. The results provide the basis for a new mechanism of cyanide detoxification and assimilation in which keto acids play an essential role.

APA, Harvard, Vancouver, ISO, and other styles

6

Schrader, Thomas. "A Chiral Cyanohydrin Phosphate for Carbonyl Umpolung—Stereoselective Synthesis of Tertiary Cyanohydrins." Angewandte Chemie International Edition in English 34, no. 8 (May 2, 1995): 917–19. http://dx.doi.org/10.1002/anie.199509171.

Full text

APA, Harvard, Vancouver, ISO, and other styles

7

Schrader, Thomas. "Stereoselective Umpolung Reactions with MetalatedP-Chiral Cyanohydrin Phosphates—Enantioselective Synthesis of Tertiary Cyanohydrins." Chemistry - A European Journal 3, no. 8 (August 1997): 1273–82. http://dx.doi.org/10.1002/chem.19970030815.

Full text

APA, Harvard, Vancouver, ISO, and other styles

8

SCHRADER, T. "ChemInform Abstract: Chiral Cyanohydrin Phosphates. Part 2. Stereoselective Umpolung Reactions with Metalated P-Chiral Cyanohydrin Phosphates- Enantioselective Synthesis of Tertiary Cyanohydrins." ChemInform 28, no. 48 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199748028.

Full text

APA, Harvard, Vancouver, ISO, and other styles

9

SCHRADER, T. "ChemInform Abstract: A Chiral Cyanohydrin Phosphate for Carbonyl Umpolung - Stereoselective Synthesis of Tertiary Cyanohydrins." ChemInform 26, no. 34 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199534123.

Full text

APA, Harvard, Vancouver, ISO, and other styles

10

DOWD, P., B. K. WILK, and M. WLOSTOWSKI. "ChemInform Abstract: A Convenient Procedure for the Preparation of Alkyl Nitriles from Alkyl Halides. Acetone Cyanohydrine as an in situ Source of Cyanide Ion." ChemInform 24, no. 50 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199350158.

Full text

APA, Harvard, Vancouver, ISO, and other styles

11

Yaragorla, Srinivasarao, A. Sudhakar, and N. Kiranmai. "ChemInform Abstract: Tris(pentafluorophenyl)borane Catalyzed Synthesis of Cyanohydrins, Cyanohydrin Trimethylsilyl Ethers and α-Amino Nitriles." ChemInform 46, no. 18 (April 16, 2015): no. http://dx.doi.org/10.1002/chin.201518094.

Full text

APA, Harvard, Vancouver, ISO, and other styles

12

Torres Domínguez, Héctor Manuel, Luis Mauricio Hernández Villaverde, and Ronan Le Lagadec. "Recent Advances on O-Ethoxycarbonyl and O-Acyl Protected Cyanohydrins." Molecules 26, no. 15 (August 3, 2021): 4691. http://dx.doi.org/10.3390/molecules26154691.

Full text

Abstract:

Ethoxycarbonyl cyanohydrins and O-acyl cyanohydrins are examples of O-protected cyanohydrins in which the protecting group presents an electrophilic center, contributing to additional reaction pathways. The first section of this review describes recent advances on the synthesis of O-ethoxycarbonyl and O-acyl protected cyanohydrins. Reactions using KCN or alkyl cyanoformates as the cyanide ion source are described, as well as organic and transition metal catalysis used in their preparation, including asymmetric cyanation. In a second part, transformations, and synthetic applications of O-ethoxycarbonyl/acyl cyanohydrins are presented. A variety of structures has been obtained starting from such protected cyanohydrins and, in particular, the synthesis of oxazoles, 1,4-diketones, 1,3-diketones, 2-vinyl-2-cyclopentenones through various methods are discussed.

APA, Harvard, Vancouver, ISO, and other styles

13

Pinkerton, A. A., P. A. Carrupt, and P. Vogel. "Optical resolution of bicyclic cyanohydrins. The structure of the hydrogen-bonded brucine–cyanohydrin complex derived from (+)-norbornenone." Acta Crystallographica Section A Foundations of Crystallography 43, a1 (August 12, 1987): C75. http://dx.doi.org/10.1107/s0108767387083478.

Full text

APA, Harvard, Vancouver, ISO, and other styles

14

Gountzos, H., WR Jackson, and KJ Harrington. "Asymmetric Hydrocyanation of Aldehydes in Crystalline Beta-Cyclodextrin Complexes." Australian Journal of Chemistry 39, no. 7 (1986): 1135. http://dx.doi.org/10.1071/ch9861135.

Full text

Abstract:

Exposure of crystalline β- cyclodextrin complexes of aldehydes to hydrogen cyanide gives cyanohydrins in moderate to good yields. The hydrocyanation reaction displayed enantioselection, and the cyanohydrins were formed with optical yields in the range from 0 to 33%.

APA, Harvard, Vancouver, ISO, and other styles

15

Leemans, Laura, Luuk van Langen, Frank Hollmann, and Anett Schallmey. "Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin." Catalysts 9, no. 6 (June 12, 2019): 522. http://dx.doi.org/10.3390/catal9060522.

Full text

Abstract:

A concurrent bienzymatic cascade for the synthesis of optically pure (S)-4-methoxymandelonitrile benzoate ((S)-3) starting from 4-anisaldehyde (1) has been developed. The cascade involves an enantioselective Manihot esculenta hydroxynitrile lyase-catalyzed hydrocyanation of 1, and the subsequent benzoylation of the resulting cyanohydrin (S)-2 catalyzed by Candida antarctica lipase A in organic solvent. To accomplish this new direct synthesis of the protected enantiopure cyanohydrin, both enzymes were immobilized and each biocatalytic step was studied separately in search for a window of compatibility. In addition, potential cross-interactions between the two reactions were identified. Optimization of the cascade resulted in 81% conversion of the aldehyde to the corresponding benzoyl cyanohydrin with 98% enantiomeric excess.

APA, Harvard, Vancouver, ISO, and other styles

16

Wingstrand, Erica, Stina Lundgren, Maël Penhoat, and Christina Moberg. "Dual Lewis acid - Lewis base activation in enantioselective additions to aldehydes." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 409–14. http://dx.doi.org/10.1351/pac200678020409.

Full text

Abstract:

Reaction of benzaldehyde with ethyl cyanoformate in the presence of Lewis acidic Ti(IV) complexes of bispyridylamide or salen ligands and Lewis basic amines affords the O-alkoxycarbonylated cyanohydrin. In the presence of the salen-based catalytic system, acetyl cyanide can also be added to benzaldehyde, providing a highly enantioselective direct route to the O-acetylated cyanohydrin.

APA, Harvard, Vancouver, ISO, and other styles

17

Baum, Stefanie, Dael S. Williamson, Trevor Sewell, and Andreas Stolz. "Conversion of Sterically Demanding α,α-Disubstituted Phenylacetonitriles by the Arylacetonitrilase from Pseudomonas fluorescens EBC191." Applied and Environmental Microbiology 78, no. 1 (October 21, 2011): 48–57. http://dx.doi.org/10.1128/aem.05570-11.

Full text

Abstract:

ABSTRACTThe nitrilase fromPseudomonas fluorescensEBC191 converted 2-methyl-2-phenylpropionitrile, which contains a quaternary carbon atom in the α-position toward the nitrile group, and also similar sterically demanding substrates, such as 2-hydroxy-2-phenylpropionitrile (acetophenone cyanohydrin) or 2-acetyloxy-2-methylphenylacetonitrile. 2-Methyl-2-phenylpropionitrile was hydrolyzed to almost stoichiometric amounts of the corresponding acid. Acetophenone cyanohydrin was transformed to the corresponding acid (atrolactate) and amide (atrolactamide) at a ratio of about 3.4:1. The (R)-acid and the (S)-amide were formed preferentially from acetophenone cyanohydrin. A homology model of the nitrilase suggested that steric hindrance with amino acid residue Tyr54 could impair the binding or conversion of sterically demanding substrates. Therefore, several enzyme variants that carried mutations in the respective residues were generated and subsequently analyzed for the substrate specificity and enantioselectivity of the reactions. Enzyme variants that demonstrated increased relative activities for the conversion of acetophenone cyanohydrin were identified. The chiral analysis of these reactions demonstrated peculiar reaction kinetics, which suggested that the enzyme variants converted the nonpreferred (S)-enantiomer of acetophenone cyanohydrin with a higher reaction rate than that of the (preferred) (R)-enantiomer. Recombinant whole-cell catalysts that simultaneously produced the nitrilase fromP. fluorescensEBC191 and a plant-derived (S)-oxynitrilase from cassava (Manihot esculenta) converted acetophenone plus cyanide at pH 4.5 to (S)-atrolactate and (S)-atrolactamide. These recombinant cells are promising catalysts for the synthesis of stable chiral quaternary carbon centers from ketones.

APA, Harvard, Vancouver, ISO, and other styles

18

Rufino, Marcos Natal, Marney Pascoli Cereda, Wanessa Teixeira Gomes Barreto, Alanderson Rodrigues da Silva, Gisele Braziliano de Andrade, and Heitor Miraglia Herrera. "Pathological effects of acetone cyanohydrin in swiss rats." Ciência e Agrotecnologia 40, no. 5 (October 2016): 577–84. http://dx.doi.org/10.1590/1413-70542016405049015.

Full text

Abstract:

ABSTRACT Cassava has been widely used for animal and human nutrition. It has also been demonstrated to have antineoplastic and anthelmintic properties. Toxicity due to cassava consumption has been reported in ruminants and laboratory animals; therefore, this study aimed to investigate the toxic effects of acetone cyanohydrin, a metabolite of linamarin that is present in cassava, in Wistar rats. Six groups of five animals each were used to evaluate the toxic effects of acetone cyanohydrin administered at 25 (G1), 50 (G2), 75 (G3), 100 (G4) and 125 (G5) µmol/kg as a single oral dose. The control group received acidified water (pH 3.5). The animals were monitored after administration of acetone cyanohydrin, and clinical symptoms were recorded. Serum enzyme levels were measured to assess the kidney and liver function. During necropsy, tissue samples were collected for histopathological examination. After administration, some animals in the G2, G4, and G5 groups presented neurological symptoms such as convulsions, involuntary muscle contraction, staggering gait, motor coordination disability, prostration, and mydriasis. All of the animals in the G5 and four animals in the G4 group died seven minutes after the administration of acetone cyanohydrin. Animals in the other groups, particularly in G2, recovered from the acute phase. Biochemical analysis revealed hepatic lesions and liver dysfunction. Histopathology revealed severe lesions in both the liver and brain. In conclusion, acetone cyanohydrin has toxic effects in the liver, lung, and central nervous system in rats; however, at concentrations up to 25 µmol/kg, the animals could survive the acute phase.

APA, Harvard, Vancouver, ISO, and other styles

19

EFFENBERGER, F., B. GUTTERER, T. ZIEGLER, E. ECKHARDT, and R. AICHHOLZ. "ChemInform Abstract: Enzyme-Catalyzed Reactions. Part 7. Enantioselective Esterification of Racemic Cyanohydrins and Enantioselective Hydrolysis or Transesterification of Cyanohydrin Esters by Lipases." ChemInform 22, no. 17 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199117045.

Full text

APA, Harvard, Vancouver, ISO, and other styles

20

Delville, Mariëlle M. E., Kaspar Koch, Jan C. M. van Hest, and Floris P. J. T. Rutjes. "Chemoenzymatic flow cascade for the synthesis of protected mandelonitrile derivatives." Organic & Biomolecular Chemistry 13, no. 6 (2015): 1634–38. http://dx.doi.org/10.1039/c4ob02128b.

Full text

APA, Harvard, Vancouver, ISO, and other styles

21

Andrews, Keith G., Christopher S. Frampton, and Alan C. Spivey. "Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor." Acta Crystallographica Section C Crystal Structure Communications 69, no. 11 (October 9, 2013): 1207–11. http://dx.doi.org/10.1107/s010827011302492x.

Full text

Abstract:

The identity of the major product of Ru-catalysed alkene metathesis of two polyene substrates has been determined using density functional theory (DFT) NMR prediction, a1H–1H Total Correlated Spectroscopy (TOCSY) NMR experiment and ultimately by single-crystal X-ray crystallography. The substrates were designed as those that would potentially allow expedient access to thetrans-decalin skeleton of the natural product (−)-euonyminol, but the product was found to be a bis-cyclopentenyl-β-cyanohydrin [1-(1-hydroxycyclopent-3-en-1-yl)cyclopent-3-ene-1-carbonitrile, C11H13NO] rather than thetrans-2,3,6,7-dehydrodecalin-β-cyanohydrin.

APA, Harvard, Vancouver, ISO, and other styles

22

Betz, Richard, Franziska Betzler, and Peter Klüfers. "2-Bromobenzaldehyde cyanohydrin." Acta Crystallographica Section E Structure Reports Online 64, no. 1 (December 6, 2007): o55. http://dx.doi.org/10.1107/s1600536807049604.

Full text

APA, Harvard, Vancouver, ISO, and other styles

23

Coloma, José, Yann Guiavarc'h, Peter-Leon Hagedoorn, and Ulf Hanefeld. "Probing batch and continuous flow reactions in organic solvents: Granulicella tundricola hydroxynitrile lyase (GtHNL)." Catalysis Science & Technology 10, no. 11 (2020): 3613–21. http://dx.doi.org/10.1039/d0cy00604a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

24

Bracco, Paula, Hanna Busch, Jan von Langermann, and Ulf Hanefeld. "Enantioselective synthesis of cyanohydrins catalysed by hydroxynitrile lyases – a review." Organic & Biomolecular Chemistry 14, no. 27 (2016): 6375–89. http://dx.doi.org/10.1039/c6ob00934d.

Full text

APA, Harvard, Vancouver, ISO, and other styles

25

Azizi, Najmedin, Zahra Rahimi, and Masoumeh Alipour. "A magnetic nanoparticle catalyzed eco-friendly synthesis of cyanohydrins in a deep eutectic solvent." RSC Advances 5, no. 75 (2015): 61191–98. http://dx.doi.org/10.1039/c5ra06176h.

Full text

APA, Harvard, Vancouver, ISO, and other styles

26

Ji, Meishan, Zhen Wu, and Chen Zhu. "Visible-light-induced consecutive C–C bond fragmentation and formation for the synthesis of elusive unsymmetric 1,8-dicarbonyl compounds." Chemical Communications 55, no. 16 (2019): 2368–71. http://dx.doi.org/10.1039/c9cc00378a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

27

Caillé, Julien, Fatma Boukattaya, Fabien Boeda, Morwenna S. M. Pearson-Long, Houcine Ammar, and Philippe Bertus. "Successive addition of two different Grignard reagents to nitriles: access to α,α-disubstituted propargylamine derivatives." Organic & Biomolecular Chemistry 16, no. 9 (2018): 1519–26. http://dx.doi.org/10.1039/c7ob03047a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

28

Tao, Jing, Ting-Ting Yang, Qing-Hua Li, and Tang-Lin Liu. "Transition-metal free cyano 1,3 migration of unsaturated cyanohydrins." Organic Chemistry Frontiers 8, no. 13 (2021): 3421–26. http://dx.doi.org/10.1039/d1qo00181g.

Full text

APA, Harvard, Vancouver, ISO, and other styles

29

Liu, Sen Lin. "Highly Efficient Synthesis of Silicon-Containing (R)-Ketone-Cyanohydrin Catalyzed by (R)-Hydroxynitrilase Lyase from Prunus Domestic." Advanced Materials Research 233-235 (May 2011): 1494–97. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.1494.

Full text

Abstract:

The synthesis of chiral silicon-containing (R)-ketone-cyanohydrin by enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin was efficiently carried out using defattedPrunus domesticseed meal as (R)-hydroxynitrilase lyase for the first time. Under the optimal conditions including a reaction temperature of 25-35°C and a buffer pH of 5.0-5.4, both acetyltrimethylsilane conversion and enantiomeric excess of the product were above 99%. In contrast, this enzyme did not accepted its carbon counterpart 3,3-dimethyl-2-butanone as substrate. These results demonstrated that the silicon atom in substrate served as a more effective atom than the carbon atom to enhance the activity of the enzyme.

APA, Harvard, Vancouver, ISO, and other styles

30

Li, Zhao-Feng, Qian Li, Li-Qing Ren, Qing-Hua Li, Yun-Gui Peng, and Tang-Lin Liu. "Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone." Chemical Science 10, no. 22 (2019): 5787–92. http://dx.doi.org/10.1039/c9sc00640k.

Full text

APA, Harvard, Vancouver, ISO, and other styles

31

Nauth, Alexander M., Tim Konrad, Zaneta Papadopulu, Nina Vierengel, Benjamin Lipp, and Till Opatz. "Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources." Green Chemistry 20, no. 18 (2018): 4217–23. http://dx.doi.org/10.1039/c8gc01730a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

32

Inagaki, Minoru, Jun Hiratake, Takaaki Nishioka, and Junichi Oda. "One-pot synthesis of optically active cyanohydrin acetates from aldehydes via lipase-catalyzed kinetic resolution coupled with in situ formation and racemization of cyanohydrins." Journal of Organic Chemistry 57, no. 21 (October 1992): 5643–49. http://dx.doi.org/10.1021/jo00047a016.

Full text

APA, Harvard, Vancouver, ISO, and other styles

33

Donohue, AC, and WR Jackson. "Attempted Enantioselective Synthesis of Terbutaline. Unexpected Partial Racemization During Lithium Aluminum Hydride Reduction of a Secondary Amide." Australian Journal of Chemistry 48, no. 10 (1995): 1741. http://dx.doi.org/10.1071/ch9951741.

Full text

Abstract:

Syntheses leading to compounds related to the bronchodilator (–)- terbutaline via optically active cyanohydrins suffered unexpected partial racemization during lithium aluminium hydride reduction of key amide intermediates.

APA, Harvard, Vancouver, ISO, and other styles

34

Zhao, Lang, and Wei-Wei Liao. "Pd-Catalyzed intramolecular C–H addition to the cyano-group: construction of functionalized 2,3-fused thiophene scaffolds." Organic Chemistry Frontiers 5, no. 5 (2018): 801–5. http://dx.doi.org/10.1039/c7qo01000a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

35

Ortega-Caballero, Fernando, and Mikael Bols. "Cyclodextrin derivatives with cyanohydrin and carboxylate groups as artificial glycosidases." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 650–58. http://dx.doi.org/10.1139/v06-039.

Full text

Abstract:

Two cyclodextrin derivatives (1 and 2) were prepared in an attempt to create glycosidase mimics with a general acid catalyst and a nucleophilic carboxylate group. The catalysts 1 and 2 were found to catalyse the hydrolysis of 4-nitrophenyl β-D-glucopyranoside at pH 8.0, but rapidly underwent decomposition with loss of hydrogen cyanide to convert the cyanohydrin to the corresponding aldehyde. The initial rate of the catalysis shows that the cyanohydrin group in these molecules functions as a good catalyst, but that the carboxylate has no positive effect. The decomposition product aldehydes display little or no catalysis. A mechanism for the decomposition is suggested.Key words: biomimicry, enzyme model, kinetics, intramolecular reaction.

APA, Harvard, Vancouver, ISO, and other styles

36

Ramalho, Rondon Tosta, Ricardo Dutra Aydos, and Marney Pascoli Cereda. "Evaluation of acetone cyanohydrin effect in "in vitro" inativation of the Ehrlich ascites tumor cells." Acta Cirurgica Brasileira 25, no. 1 (February 2010): 111–16. http://dx.doi.org/10.1590/s0102-86502010000100022.

Full text

Abstract:

PURPOSE: To evaluate the antitumor effect of acetone cyanohydrin in Ehrlich ascites tumor cells in vitro. METHODS: The Ehrlich ascites tumor cells and lymphocytes were incubated with different concentrations of acetone cyanohydrin (0, 0.5, 1.0, 2.0, 10.0, 20.0 and 30.0 μg.mL-1), After 1, 2, 3, 4, 18 and 24 hours cell viability tests were performed by the trypan blue method. RESULTS: The results demonstrated a dose-dependent cytotoxic effect against the cells of Ehrlich ascites tumor. The concentrations of 20 and 30 μg.mL-1 was 100% of cell death in only 1 and 2 hours respectively. In lower doses of 0.5, 1.0 and 2.0 μg.mL-1 the cytotoxic effect was less intense, increasing gradually with time. CONCLUSIONS: At low concentrations of 0.5, 1.0 and 2.0 μg.mL-1, more than 90% of cell death was observed only after 24 hours of incubation which is the evidence that the tumor cell has the ability to poison cumulatively and irreversibly itself with the acetone cyanohydrin when compared with the results presented by human lymphocytes that the same doses and at the same time of incubation reached a maximum of 30% of cell death, suggesting an activity of rhodanese differentiated between the two cells.

APA, Harvard, Vancouver, ISO, and other styles

37

Liu, Tang-Lin, Zhao-Feng Li, Jing Tao, Qing-Hua Li, Wan-Fang Li, Qian Li, Li-Qing Ren, and Yun-Gui Peng. "Cyano-borrowing: titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples." Chemical Communications 56, no. 4 (2020): 651–54. http://dx.doi.org/10.1039/c9cc08576a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

38

Chen, Fu-Xue, and Xiaoming Feng. "Asymmetric Synthesis of Cyanohydrins." Current Organic Synthesis 3, no. 1 (February 1, 2006): 77–97. http://dx.doi.org/10.2174/157017906775473948.

Full text

APA, Harvard, Vancouver, ISO, and other styles

39

Fomunyam, R. "The stability of cyanohydrins." Food Chemistry 17, no. 3 (1985): 221–25. http://dx.doi.org/10.1016/0308-8146(85)90072-x.

Full text

APA, Harvard, Vancouver, ISO, and other styles

40

Turnbull, Ben W. H., Jungha Chae, Samuel Oliver, and P. Andrew Evans. "Regio- and stereospecific rhodium-catalyzed allylic alkylation with an acyl anion equivalent: an approach to acyclic α-ternary β,γ-unsaturated aryl ketones." Chemical Science 8, no. 5 (2017): 4001–5. http://dx.doi.org/10.1039/c6sc05705e.

Full text

Abstract:

The regio- and stereospecific rhodium-catalyzed allylic alkylation of secondary allylic carbonates with cyanohydrin pronucleophiles facilitates the direct construction of acyclic α-ternary β,γ-unsaturated aryl ketones.

APA, Harvard, Vancouver, ISO, and other styles

41

Dixon, Brian G., and A. T. Andrew. "Hydrolysis of cyanohydrin esters." Tetrahedron 42, no. 4 (January 1986): 1123–26. http://dx.doi.org/10.1016/s0040-4020(01)87516-5.

Full text

APA, Harvard, Vancouver, ISO, and other styles

42

North, Michael. "Catalytic Asymmetric Cyanohydrin Synthesis." Synlett 1993, no. 11 (1993): 807–20. http://dx.doi.org/10.1055/s-1993-22618.

Full text

APA, Harvard, Vancouver, ISO, and other styles

43

Olafsdottir, Elin S., Jerzy W. Jaroszewski, and Maria Mercedes Arbo. "Cyanohydrin glucosides of turneraceae." Biochemical Systematics and Ecology 18, no. 6 (October 1990): 435–38. http://dx.doi.org/10.1016/0305-1978(90)90089-x.

Full text

APA, Harvard, Vancouver, ISO, and other styles

44

Olafsdottir, Elin S., Jan Vanggaard Andersen, and Jerzy W. Jaroszewski. "Cyanohydrin glycosides of passifloraceae☆." Phytochemistry 28, no. 1 (1989): 127–32. http://dx.doi.org/10.1016/0031-9422(89)85023-x.

Full text

APA, Harvard, Vancouver, ISO, and other styles

45

Matthews, BR, WR Jackson, HA Jacobs, and KG Watson. "Synthesis of Aryl Carbohydrate Synthons and 2,3-Dihydroxypropanoic Acid-Derivatives of High Optical Purity." Australian Journal of Chemistry 43, no. 7 (1990): 1195. http://dx.doi.org/10.1071/ch9901195.

Full text

Abstract:

General routes to both L and D aryl carbohydrate precursors and to erythro and threo 2,3-dihydroxypropanoic acids of high optical purity have been established from readily available optically active aryl cyanohydrins.

APA, Harvard, Vancouver, ISO, and other styles

46

Taniguchi, Takashi, Yasuaki Taketomo, Mizuki Moriyama, Noritada Matsuo, and Yoo Tanabe. "Synthesis and Stereostructure-Activity Relationship of Novel Pyrethroids Possessing two Asymmetric Centers on a Cyclopropane Ring." Molecules 24, no. 6 (March 14, 2019): 1023. http://dx.doi.org/10.3390/molecules24061023.

Full text

Abstract:

2-Methylcyclopropane pyrethroid insecticides bearing chiral cyanohydrin esters or chiral ethers and two asymmetric centers on the cyclopropane ring, were synthesized. These compounds were designed using a “reverse connection approach” between the isopropyl group in Fenvalerate, and between two dimethyl groups in an Etofenprox analogue (the methyl, ethyl form), respectively. These syntheses were achieved by accessible ring opening reactions of commercially available (±)-, (R)-, and (S)-propylene oxides using 4-chlorobenzyl cyanide anion as the crucial step, giving good overall yield of the product with >98% ee. The insecticidal activity against the common mosquito (Culex pipiens pallens) was assessed for pairs of achiral diastereomeric (1R*,2S*)-, (1R*,2R*)-cyanohydrin esters, and (1R*,2S*)-, (1R*,2R*)-ethers; only the (1R*,2R*)-ether was significantly effective. For the enantiomeric (1S,2S)-ether and (1R,2R)-ether, the activity was clearly centered on the (1R,2R)-ether. The present stereostructure‒activity relationship revealed that (i) cyanohydrin esters derived from fenvalerate were unexpectedly inactive, whereas ethers derived from etofenprox were active, and (ii) apparent chiral discrimination between the (1S,2S)-ether and the (1R,2R)-ether was observed. During the present synthetic study, we performed alternative convergent syntheses of Etofenprox and novel 4-EtO-type (1S,2S)- and (1R,2R)-pyrethroids from the corresponding parent 4-Cl-type pyrethroids, by utilizing a recently-developed hydroxylation cross-coupling reaction.

APA, Harvard, Vancouver, ISO, and other styles

47

Sumino, Shuhei, Akira Fusano, Hiroyuki Okai, Takahide Fukuyama, and Ilhyong Ryu. "One-pot synthesis of cyanohydrin derivatives from alkyl bromides via incorporation of two one-carbon components by consecutive radical/ionic reactions." Beilstein Journal of Organic Chemistry 10 (January 14, 2014): 150–54. http://dx.doi.org/10.3762/bjoc.10.12.

Full text

Abstract:

The consecutive radical/ionic reaction consisting of radical formylation of alkyl bromides and nucleophilic addition of a cyanide ion was investigated, which gave moderate to good yields of cyanohydrin derivatives in one-pot.

APA, Harvard, Vancouver, ISO, and other styles

48

Liu, Yu, Duodong Zhang, Yangyang Ma, Jiayun Li, Ying Bai, and Jiajian Peng. "The Hydrosilylation and Cyanosilylation of Ketones Catalyzed using Metal Borohydrides." Current Organic Synthesis 16, no. 2 (March 26, 2019): 276–82. http://dx.doi.org/10.2174/1570179415666181114111939.

Full text

Abstract:

Aim and Objective: The hydrosilylation reaction of carbonyl compounds has emerged as a powerful method in organic synthesis. The catalytic hydrosilylation of ketones is a valuable transformation because it generates protected cyanosilylation reaction of carbonyl compounds is an efficient procedure for the synthesis of silylated cyanohydrins, which are readily converted into useful functionalized compounds, such as cyanohydrins, α-hydroxy acids, β-amino alcohols and other biologically active compounds. Materials and Methods: A facile, economic and efficient method has been developed for the hydrosilylation and cyanosilylation of ketones using metal borohydrides. A series of silylated ethers and silylated cyanohydrins can be isolated via direct distillation. Results: The catalytic properties of a range of metal borohydrides in the hydrosilylation reaction of acetophenone with diphenylsilane were investigated. The relative catalytic activity of the borohydride catalyst studied was as follows: (CH3)4NBH4> (PhCH2)(CH3)3NBH4> (CH2CH3)4NBH4> (CH3CH2CH2CH3)4NBH4> NaBH4> KBH4> LiBH4. The cyanosilylation of acetophenone using trimethylsilyl cyanide (TMSCN) in the presence of NaBH4 occurred under similar reaction conditions. An excellent reaction rate and high conversion were obtained. Conclusion: The metal borohydride-catalyzed hydrosilylation alcohols in one step. The and cyanosilylation of ketones could be carried out smoothly under mild reaction conditions. Among the metal borohydrides studied, an excellent reaction rate and high conversion were obtained using NaBH4, NaBH (CH2CH3)3 or (alkyl)4 NBH4 as the reaction catalyst.

APA, Harvard, Vancouver, ISO, and other styles

49

Dadashipour, Mohammad, Yuko Ishida, Kazunori Yamamoto, and Yasuhisa Asano. "Discovery and molecular and biocatalytic properties of hydroxynitrile lyase from an invasive millipede,Chamberlinius hualienensis." Proceedings of the National Academy of Sciences 112, no. 34 (August 10, 2015): 10605–10. http://dx.doi.org/10.1073/pnas.1508311112.

Full text

Abstract:

Hydroxynitrile lyase (HNL) catalyzes the degradation of cyanohydrins and causes the release of hydrogen cyanide (cyanogenesis). HNL can enantioselectively produce cyanohydrins, which are valuable building blocks for the synthesis of fine chemicals and pharmaceuticals, and is used as an important biocatalyst in industrial biotechnology. Currently, HNLs are isolated from plants and bacteria. Because industrial biotechnology requires more efficient and stable enzymes for sustainable development, we must continuously explore other potential enzyme sources for the desired HNLs. Despite the abundance of cyanogenic millipedes in the world, there has been no precise study of the HNLs from these arthropods. Here we report the isolation of HNL from the cyanide-emitting invasive millipedeChamberlinius hualienensis, along with its molecular properties and application in biocatalysis. The purified enzyme displays a very high specific activity in the synthesis of mandelonitrile. It is a glycosylated homodimer protein and shows no apparent sequence identity or homology with proteins in the known databases. It shows biocatalytic activity for the condensation of various aromatic aldehydes with potassium cyanide to produce cyanohydrins and has high stability over a wide range of temperatures and pH values. It catalyzes the synthesis of (R)-mandelonitrile from benzaldehyde with a 99% enantiomeric excess, without using any organic solvents. Arthropod fauna comprise 80% of terrestrial animals. We propose that these animals can be valuable resources for exploring not only HNLs but also diverse, efficient, and stable biocatalysts in industrial biotechnology.

APA, Harvard, Vancouver, ISO, and other styles

50

Tasic, Gordana, Radomir Matovic, and Radomir Saicic. "Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach." Journal of the Serbian Chemical Society 69, no. 11 (2004): 981–90. http://dx.doi.org/10.2298/jsc0411981t.

Full text

Abstract:

A method for the stereoselective homologation of ?-amino acids into syn-?-hydroxy-?-amino acids is described, based on the conversion of stereoisomeric cyanohydrins into trans-oxazolines. The synthetic potential of the method is illustrated in the enantioselective formal synthesis of Bestatin.

APA, Harvard, Vancouver, ISO, and other styles

We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!