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Journal articles on the topic 'Racemique'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Aziz, Mostafa, and Francis Rouessac. "Syntheses en serie racemique et en serie optiquement active d'une famille de derives oxygenes naturels de l'ombelliferone. Structure spatiale du (-)epoxy-3'6' auraptene." Tetrahedron 44, no. 1 (January 1988): 101–10. http://dx.doi.org/10.1016/s0040-4020(01)85097-3.

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2

Karume, Ibrahim, Musa M. Musa, Odey Bsharat, Masateru Takahashi, Samir M. Hamdan, and Bassam El Ali. "Dual enzymatic dynamic kinetic resolution by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase and Candida antarctica lipase B." RSC Advances 6, no. 99 (2016): 96616–22. http://dx.doi.org/10.1039/c6ra18895h.

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The immobilization of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (TeSADH) using sol–gel method enables its use to racemize enantiopure alcohols in organic media, thus allows for a dual enzymatic dynamic kinetic resolution.

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3

Broberg, Anders, Christina Nord, Jolanta J. Levenfors, Joakim Bjerketorp, Bengt Guss, and Bo Öberg. "In-peptide amino acid racemization via inter-residue oxazoline intermediates during acidic hydrolysis." Amino Acids 53, no. 3 (February 13, 2021): 323–31. http://dx.doi.org/10.1007/s00726-021-02951-7.

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AbstractIsopedopeptins are antibiotic cyclic lipodepsipeptides containing the subsequence L-Thr—L-2,3-diaminopropanoic acid—D-Phe—L-Val/L-3-hydroxyvaline. Acidic hydrolysis of isopedopeptins in D2O showed the D-Phe residues to racemize extensively in peptides with L-3-hydroxyvaline but not in peptides with L-Val. Similarly, one Leu residue in pedopeptins, which are related peptides containing the subsequence Leu—2,3-diaminopropanoic acid—Leu—L-Val/L-3-hydroxyvaline, was found to racemize in peptides with L-3-hydroxyvaline. Model tetrapeptides, L-Ala—L-Phe—L-Val/3-hydroxyvaline—L-Ala, gave the corresponding results, i.e. racemization of L-Phe only when linked to a L-3-hydroxyvaline. We propose the racemization to proceed via an oxazoline intermediate involving Phe/Leu and the L-3-hydroxyvaline residues. The 3-hydroxyvaline residue may form a stable tertiary carbocation by loss of the sidechain hydroxyl group as water after protonation. Elimination of the Phe/Leu H-2 and ring-closure from the carbonyl oxygen onto the carbocation results in the suggested oxazoline intermediate. The reversed reaction leads to either retained or inversed configuration of Phe/Leu. Such racemization during acidic hydrolysis may occur whenever a 3-hydroxyvaline residue or any amino acid that can form a stable carbocation on the C-3, is present in a peptide. The proposed mechanism for racemization was supported by incorporation of 18O in the 3-hydroxyvaline sidechain when the acidic hydrolysis was performed in H2O/H218O (1:1). The 2,3-diaminopropanoic residues of isopedopeptins and pedopeptins were also found to racemize during acidic hydrolysis, as previously described. Based on the results, the configuration of the Leu and 2,3-diaminopropanoic acid residues of the pedopeptins were reassigned to be L-Leu and D-Leu, and 2 × L-2,3-diaminopropanoic acid.

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4

Slebioda, Marek, Marc A. St-Amand, Francis M. F. Chen, and N. Leo Benoiton. "Studies on the kinetics of racemization of 2,4-disubstituted-5(4H)-oxazolones." Canadian Journal of Chemistry 66, no. 10 (October 1, 1988): 2540–44. http://dx.doi.org/10.1139/v88-398.

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The kinetics of racemization of 2,4-disubstituted-5(4H)-oxazolones obtained from N-acetyl, N-benzoyl, and N-benzyloxycarbonylglycyl-L-leucine, -valine, and -phenylalanine have been studied in several solvents alone and in the presence of tertiary amines. The influence of the nature of the substituents on the rate of the reaction has been evaluated, and the values of the activation parameters ΔH≠ and ΔS≠ for the base-catalyzed reactions have been determined. The racemization process is governed by electronic effects of the C(2)-substituents and steric effects of the C(4)-substituents of the oxazolones. The thermodynamic data suggest that the 2-substituted-4-benzyl-5(4H)-oxazolones racemize more readily than the 4-alkyl analogues (alkyl ≠ benzyl) because of the unique conformation assumed by the benzyl substituent. The rate of the base-catalyzed reaction depends on the extent of hindrance about the nitrogen atom of the tertiary amine as well as on its basicity. The data suggest that the relative rates of racemization of oxazolones are not a true reflection of the relative tendencies to racemize of the pertinent residues during couplings of the parent acids.

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5

Fujitaka, Yuya, Daisuke Uesugi, Hatsuyuki Hamada, Hiroki Hamada, Kei Shimoda, Masayoshi Yanagi, Manami Inoue, and Shin-ichi Ozaki. "Application of Racemization Process to Dynamic Resolution of (RS)-Phenylephrine to (R)-Phenylephrine β-D-Glucoside by Nicotiana tabacum Glucosyltransferase." Natural Product Communications 13, no. 11 (November 2018): 1934578X1801301. http://dx.doi.org/10.1177/1934578x1801301113.

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Enzymatic glucosylation of racemic phenylephrine by glucosyltransferase from Nicotiana tabacum gave ( R)-phenylephrine glucoside and recovered ( S)-phenylephrine. [RuCl2( p-cymene)]2 complex associated with simple hemisalen ligands or zeolite were able to racemize ( S)-phenylephrine. The [RuCl2( p-cymene)]2/Ligand/TEMPO or zeolite racemization was associated with the enantioselective glycosylation of racemic phenylephrine with glucosyltransferase. The ( R)-stereoselective glucosylation of ( RS)-phenylephrine occurred to produce a high yield of ( R)-phenylephrine glucoside in high yield.

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6

Aziz, Mostafa, and Francis Rouessac. "Syntheses de la (+)-marmine, des (+)-epoxy-6′,7′- et (-)-epoxy-3′,6′-auraptenes et des racemiques correspondants." Tetrahedron Letters 28, no. 23 (January 1987): 2579–82. http://dx.doi.org/10.1016/s0040-4039(00)96152-5.

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7

Fraschetti, Caterina, Maurizio Speranza, and Antonello Filippi. "Does a chiral alcohol really racemize when its OH group is protected with Boyer's reaction?" Chirality 22, no. 1 (January 2010): 88–91. http://dx.doi.org/10.1002/chir.20710.

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8

MURINDA, SHELTON E., ROBERT F. ROBERTS, and STEPHANIE DOORES. "Evaluation of Lactic Acid–Producing Bacillus and Sporolactobacillus for Antilisterial Activity." Journal of Food Protection 58, no. 5 (May 1, 1995): 570–72. http://dx.doi.org/10.4315/0362-028x-58.5.570.

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Fifty-five strains of Bacillus (53 B. laevolacticus and 2 B. racemilacticus) and 31 strains of Sporolactobacillus (3 S. inulinus, 19 S. laevus, and 9 S. racemicus) were screened for specific inhibitory activity against 8 strains of Listeria monocytogenes. Putative producer strains were propagated in Eugon, lactobacillus MRS, or sporolactobacillus broths (48–96 h, 37°C, 9.4% CO2), Assays to detect inhibition of Listeria monocytogenes were carried out on Eugon or Bacto-Agar at 37°C (9.4% CO2). Inhibition was absent in direct assays using spot-on-the-lawn techniques but was found in well diffusion assays, and in deferred assays using stabinoculation techniques. Cell-free supernatant fluids of cultured MRS broths demonstrated superior inhibition to cell-free supernatants from Eugon and sporolactobacillus broths. The inhibitory activity of cell-free supernatant fluids was lost after neutralization (0.5M NaOH) or by dialysis (10,000 Da exclusion limit). The observed inhibition was most likely due to production of lactic acid.

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9

Setchell, Kenneth D. R., James E. Heubi, Kevin E. Bove, Nancy C. O'Connell, Tracy Brewsaugh, Steven J. Steinberg, Ann Moser, and Robert H. Squires. "Liver disease caused by failure to racemize trihydroxycholestanoic acid: Gene mutation and effect of bile acid therapy." Gastroenterology 124, no. 1 (January 2003): 217–32. http://dx.doi.org/10.1053/gast.2003.50017.

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10

Horak, Jeannie, and Michael Lämmerhofer. "Derivatize, Racemize, and Analyze—an Easy and Simple Procedure for Chiral Amino Acid Standard Preparation for Enantioselective Metabolomics." Analytical Chemistry 91, no. 12 (May 14, 2019): 7679–89. http://dx.doi.org/10.1021/acs.analchem.9b00666.

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11

Harriehausen, Isabel, Jonas Bollmann, Thiane Carneiro, Katja Bettenbrock, and Andreas Seidel-Morgenstern. "Characterization of an Immobilized Amino Acid Racemase for Potential Application in Enantioselective Chromatographic Resolution Processes." Catalysts 11, no. 6 (June 11, 2021): 726. http://dx.doi.org/10.3390/catal11060726.

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Enantioselective resolution processes can be improved by integration of racemization. Applying environmentally friendly enzymatic racemization under mild conditions is in particular attractive. Owing to the variety of enzymes and the progress in enzyme engineering, suitable racemases can be found for many chiral systems. An amino acid racemase (AAR) from P. putida KT2440 is capable of processing a broad spectrum of amino acids at fast conversion rates. The focus of this study is the evaluation of the potential of integrating AAR immobilized on Purolite ECR 8309 to racemize L- or D-methionine (Met) within an enantioselective chromatographic resolution process. Racemization rates were studied for different temperatures, pH values, and fractions of organic co-solvents. The long-term stability of the immobilized enzyme at operating and storage conditions was found to be excellent and recyclability using water with up to 5 vol% ethanol at 20 °C could be demonstrated. Packed as an enzymatic fixed bed reactor, the immobilized AAR can be coupled with different resolution processes; for instance, with chromatography or with preferential crystallization. The performance of coupling it with enantioselective chromatography is estimated quantitatively, exploiting parametrized sub-models. To indicate the large potential of the AAR, racemization rates are finally given for lysine, arginine, serine, glutamine, and asparagine.

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12

Cossery, J. M., C. Perdicakis, G. Coudert, G. Guillaumet, and L. Pichat. "Isosteres Oxygenes d'Hydroxy-di-n-Propylaminotetralines Syntheses de Monomethoxy et Monohydroxy- (DI-N-Propylamino)-3 Chromannes [n-Propyl-3H] Racemiques: Nouveaux Radioligands des Sites de Liaison Serotoninergiques 5-HT1a et Dopaminergiques D2." Journal of Labelled Compounds and Radiopharmaceuticals 25, no. 8 (August 1988): 833–54. http://dx.doi.org/10.1002/jlcr.2580250805.

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13

YANAGIDA, F., K. I. SUZUKI, M. KOZAKI, and K. KOMAGATA. "Proposal of Sporolactobacillus nakayamae subsp. nakayamae sp. nov., subsp. nov., Sporolactobacillus nakayamae subsp. racemicus subsp. nov., Sporolactobacillus terrae sp. nov., Sporolactobacillus kofuensis sp. nov., and Sporolactobacillus lactosus sp. nov." International Journal of Systematic Bacteriology 47, no. 2 (April 1, 1997): 499–504. http://dx.doi.org/10.1099/00207713-47-2-499.

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14

Rzepa, Henry S., and Marion E. Cass. "In Search of the Bailar Twist and Rây−Dutt Mechanisms That Racemize Chiral Trischelates: A Computational Study of ScIII, TiIV, CoIII, ZnII, GaIII, and GeIVComplexes of a Ligand Analogue of Acetylacetonate." Inorganic Chemistry 46, no. 24 (November 2007): 10444. http://dx.doi.org/10.1021/ic701900f.

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15

Rzepa, Henry S., and Marion E. Cass. "In Search of the Bailar and Rây−Dutt Twist Mechanisms That Racemize Chiral Trischelates: A Computational Study of ScIII, TiIV, CoIII, ZnII, GaIII, and GeIVComplexes of a Ligand Analogue of Acetylacetonate." Inorganic Chemistry 46, no. 19 (September 2007): 8024–31. http://dx.doi.org/10.1021/ic062473y.

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16

Cass, Marion E., and Henry S. Rzepa. "Visualizing Metal Tris Chelates: Visualizations to Examine the Structure and Symmetry of Metal Tris Chelates: Symmetry Operations, Chirality, and Mechanisms (Bailar Twist and Rây-Dutt) that Racemize the Δ and Λ Isomers." Journal of Chemical Education 85, no. 5 (May 2008): 750. http://dx.doi.org/10.1021/ed085p750.

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