Relevant bibliographies by topics / Cyanohydrine

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  1. Journal articles
  2. Dissertations / Theses
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  4. Conference papers

Academic literature on the topic 'Cyanohydrine'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Cyanohydrine"

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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.

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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 3a–g. In contrast, the stereoselectivity in the HNL-catalyzed addition to 4-alkanoyloxycyclohexanones 3h–k 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.
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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.

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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.
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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.

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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.
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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.

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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.
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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.

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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.
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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.

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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.

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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.

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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.

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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.

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Dissertations / Theses on the topic "Cyanohydrine"

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Carta, Paola. "Synthesis and applications of chiral cyanohydrins." Thesis, King's College London (University of London), 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.414006.

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Wingstrand, Erica. "New Methods for Chiral Cyanohydrin Synthesis." Doctoral thesis, KTH, Kemi, 2009. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-10205.

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This thesis deals with method development in asymmetric catalysis and specifically syntheses of enantioenriched O-functionalized cyanohydrins. The first part describes the development of a method for the synthesis of O‑alkoxycarbonylated and O-acylated cyanohydrins. Ethyl cyanoformate and acyl cyanides were added to aldehydes in a reaction catalyzed by a chiral dimeric Ti-salen complex together with a tertiary amine. High yields and enantioselectivities were in most cases obtained. Mechanistic studies were performed and a reaction mechanism was proposed. ­ The second part describes a method in which the undesired minor enantiomer in a Lewis acid–Lewis base-catalyzed acylcyanation is continuously recycled into prochiral starting material. Close to enantiopure O‑acylated cyanohydrins were obtained in high yields. The third part deals with asymmetric acylcyanations of ketones. Acetyl cyanide was found to add to α‑ketoesters in a reaction catalyzed by a chiral Lewis base. Yields up to 77% and 82% ee were obtained. The final part describes an enzymatic method for high-throughput analysis of O‑acylated cyanohydrins. The enantiomeric excess and conversion were determined for products obtained from a number of aromatic and aliphatic aldehydes.
QC 20100818
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Hogg, David Joseph Philip. "Mechanistic studies on asymmetric cyanohydrin synthesis." Thesis, Bangor University, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.262128.

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Lundgren, Stina. "Efficient Synthesis and Analysis of Chiral Cyanohydrins." Doctoral thesis, Stockholm : Kungliga Tekniska högskolan (KTH), 2007. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-4315.

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Young, Carl. "Asymmetric cyanohydrin synthesis using heterobimetallic salen complexes." Thesis, University of Newcastle Upon Tyne, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.500998.

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Asymmetric cyanohydrin synthesis is a broad and developing area of organic chemistry to which many groups have contributed over the years. Notably, North et al have developed highly active salen based catalysts 1 and 2 for the asymmetric addition of cyanide to aldehydes. More recent mechanistic investigations have revealed that combining complexes 1 and 2 gave interesting results indicating the possible formation of and catalysis by a new heterobimetallic complex formed in-situ. This thesis follows on from the initial study and offers good evidence for the formation of a mixed metal bimetallic catalyst possessing characteristics of each parent complex. Firstly, the catalysed addition of trimethylsilyl cyanide, potassium cyanide and ethyl cyanoformate to benzaldehyde was studied (Scheme 1) using various chiral and achiral analogues of complexes 1 and 2 to study the effects on cyanohydrin product enantiometric excess and absolute configuration.
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Heid, Berenice. "Enantioselective Preparation of ω-Functionalized O-Acylated Cyanohydrins." Thesis, KTH, Skolan för kemivetenskap (CHE), 2011. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-40896.

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A minor enantiomer recycling one-pot process usingω-functionalized prochiral aldehydes as starting materials and two reinforcing catalysts has been reported. The desired aldehyde for these process studies was 5-bromo-1-pentanal. In a two-phase solvent system, enzyme-catalyzed hydrolysis of the minor enantiomer regenerates continuously the prochiral starting material and Lewis acid catalysed addition of acetyl cyanide provides the O-acetylated cyanohydrins. The minor enantiomer recycling process has been studied and improved for 5-bromo-1-pentanal to receive high enantiomeric excess and yield of the expected O-acetylated cyanohydrin.
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Clutterbuck, Lisa. "The catalytic, asymmetric synthesis of cyanohydrins and amino nitriles." Thesis, University of Newcastle Upon Tyne, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.505844.

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Gregory, Robert John Hryntchyshyn. "Biocatalytic preparation and chemistry of some novel cyanohydrin systems." Thesis, University of Liverpool, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.365896.

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Ahmed, Takiya Janice. "The role of bone morphogenetic proteins in otic specification /." Connect to title online (Scholars' Bank) Connect to title online (ProQuest), 2008. http://hdl.handle.net/1794/8447.

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Thesis (Ph. D.)--University of Oregon, 2008.
Typescript. Includes vita and abstract. Includes bibliographical references (leaves 195-204). Also available online in ProQuest, free to University of Oregon users.
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Briechle, Sebastian Dirk [Verfasser], and Andreas [Akademischer Betreuer] Liese. "Stereoselective synthesis of cyanohydrins: process development / Sebastian Dirk Briechle. Betreuer: Andreas Liese." Hamburg-Harburg : Universitätsbibliothek der Technischen Universität Hamburg-Harburg, 2013. http://d-nb.info/1048574067/34.

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Book chapters on the topic "Cyanohydrine"

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Schomburg, Dietmar, and Dörte Stephan. "Cyanohydrin beta-glucosyltransferase." In Enzyme Handbook 12, 441–43. Berlin, Heidelberg: Springer Berlin Heidelberg, 1996. http://dx.doi.org/10.1007/978-3-642-61117-9_89.

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Gruber-Khadjawi, Mandana, Martin H. Fechter, and Herfried Griengl. "Cleavage and Formation of Cyanohydrins." In Enzyme Catalysis in Organic Synthesis, 947–90. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2012. http://dx.doi.org/10.1002/9783527639861.ch23.

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Wiedner, Romana, Helmut Schwab, and Kerstin Steiner. "Hydroxynitrile Lyases for Biocatalytic Synthesis of Chiral Cyanohydrins." In Green Biocatalysis, 603–28. Hoboken, NJ: John Wiley & Sons, Inc, 2016. http://dx.doi.org/10.1002/9781118828083.ch25.

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Josse, Solen, and Denis Postel. "Cyanohydrins and Aminocyanides as Key Intermediates to Various Spiroheterocyclic Sugars." In Topics in Heterocyclic Chemistry, 137–69. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/7081_2019_35.

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Effenberger, F. X. "(R)- and (S)-Cyanohydrins - Their Enzymatic Synthesis and Their Reactions." In Microbial Reagents in Organic Synthesis, 25–33. Dordrecht: Springer Netherlands, 1992. http://dx.doi.org/10.1007/978-94-011-2444-7_2.

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van der Gen, Arne, and Johannes Brussee. "Stereoselective Biocatalytic Formation of Cyanohydrins, Versatile Building Blocks for Organic Synthesis." In Enzymes in Action, 365–95. Dordrecht: Springer Netherlands, 2000. http://dx.doi.org/10.1007/978-94-010-0924-9_19.

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Coats, Joel R., Rong Tsao, Christopher J. Peterson, Dong-Sik Park, Angela M. Knips, David H. Soh, and Gregory L. Tylka. "Activity of Glucosinolate Aglycones and Cyanohydrin Aglycones against Nematodes, Insects, Bacteria, Fungi, and Weeds." In Biopesticides: State of the Art and Future Opportunities, 179–88. Washington, DC: American Chemical Society, 2014. http://dx.doi.org/10.1021/bk-2014-1172.ch013.

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Powell, Kimberley Jade. "Synthesis of Alkenyl Nitriles by the Palladium-Catalysed Cyanation of Vinyl Halides with Acetone Cyanohydrin." In Springer Theses, 105–30. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/978-3-319-22069-7_7.

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DeRosa, Thomas F. "Cyanohydrins." In Advances in Synthetic Organic Chemistry and Methods Reported in US Patents, 220–22. Elsevier, 2006. http://dx.doi.org/10.1016/b978-008044474-1/50026-8.

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"2.6 Cyanohydrins." In Protecting Groups, edited by Philip J. Kocieński. Stuttgart: Georg Thieme Verlag, 2005. http://dx.doi.org/10.1055/b-0035-108246.

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Conference papers on the topic "Cyanohydrine"

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de Gonzalo, Gonzalo. "Organocatalyzed synthesis of optically active cyanohydrins starting from alpha-ketoesters." In The 21st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2017. http://dx.doi.org/10.3390/ecsoc-21-04718.

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Alves, Leandro de C., André L. Desiderá, Kleber T. de Oliveira, Antonio G. Ferreira, and Timothy J. Brocksom. "Structural assignment of the trimethylsilyl-protected cyanohydrins of R-(-)-carvone." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0192-1.

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Marcus, Jan, Johannes Brussee, and Arne van der Gen. "The synthesis of y-hydroxy-a,b-unsaturated compounds from chiral cyanohydrins." In The 3rd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1999. http://dx.doi.org/10.3390/ecsoc-3-01721.

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Gerrits, Pieter, Johannes Brussee, and Arne van der Gen. "Substrate Transport Limitation as tool to enhance enantioselectivity in the enzyme synthesis of chiral cyanohydrins." In The 3rd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1999. http://dx.doi.org/10.3390/ecsoc-3-01763.

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