Biocatalytic Synthesis of Chiral N-Functionalized Amino Acids

被引：40

作者：

Hyslop, Julia F. ^{[1
,2
]}

Lovelock, Sarah L. ^{[2
,3
]}

Sutton, Peter W. ^{[4
,5
]}

Brown, Kristin K. ^{[6
]}

Watson, Allan J. B. ^{[7
]}

Roiban, Gheorghe-Doru ^{[2
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

[2] GlaxoSmithKline, Adv Mfg Technol, Med Res Ctr, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

[3] Univ Manchester, Manchester Inst Biotechnol, Sch Chem, 131 Princess St, Manchester M1 7DN, Lancs, England

[4] GlaxoSmithKline, Med Res Ctr, API Chem, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

[5] Univ Autonoma Barcelona, Dept Chem Engn, Catalunya 08193, Cerdanyola Del, Spain

[6] GlaxoSmithKline, Mol Design Computat & Modeling Sci, 1250 S Collegeville Rd, Collegeville, PA 19426 USA

[7] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 42期

关键词：

biocatalysis; ketimine reductases; N-methyl amino acid dehydrogenases; reductive amination; alpha-keto amino acids; ENANTIOSELECTIVE REDUCTIVE AMINATION; ALPHA-KETO ACIDS; DELTA(1)-PYRROLINE-5-CARBOXYLATE REDUCTASE; OPINE DEHYDROGENASE; ENZYMATIC-SYNTHESIS; PSEUDOMONAS-PUTIDA; PROTEIN CAVITY; PURIFICATION; PHENYLALANINE; ENZYMES;

D O I：

10.1002/anie.201806893

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Functionalized amino acids are important building blocks for the preparation of diverse bioactive molecules, including peptides. The development of sustainable manufacturing routes to chiral N-alkylated amino acids remains a significant challenge in the pharmaceutical and fine-chemical industries. Herein we report the discovery of a structurally diverse panel of biocatalysts which catalyze the asymmetric synthesis of N-alkyl amino acids through the reductive coupling of ketones and amines. Reactions have been performed on a gram scale to yield optically pure N-alkyl-functionalized products in high yields.

引用

页码：13821 / 13824

页数：4

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