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Biocatalytic Synthesis of Chiral N‐Functionalized Amino Acids
Author(s) -
Hyslop Julia F.,
Lovelock Sarah L.,
Sutton Peter W.,
Brown Kristin K.,
Watson Allan J. B.,
Roiban GheorgheDoru
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201806893
Subject(s) - alkyl , chemistry , amino acid , yield (engineering) , alkylation , enantioselective synthesis , organic chemistry , combinatorial chemistry , biocatalysis , catalysis , chemical synthesis , molecule , materials science , reaction mechanism , biochemistry , metallurgy , in vitro
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.