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A Biocatalytic Route to Enantiomerically Pure Unsaturated α‐H‐α‐Amino Acids
Author(s) -
Wolf Larissa B.,
Sonke Theo,
Tjen Kim C. M. F.,
Kaptein Bernard,
Broxterman Quirinus B.,
Schoemaker Hans E.,
Rutjes Floris P. J. T.
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200108)343:6/7<662::aid-adsc662>3.0.co;2-i
Subject(s) - chemistry , amino acid , amidase , pseudomonas putida , hydrolysis , enantiomeric excess , rhodococcus , enantiomer , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry , enzyme , catalysis
A set of both enantiomeric forms of non‐proteinogenic, unsaturated α‐H‐α‐amino acids was efficiently synthesized using a biocatalytic pathway. This route involved the straightforward synthesis of the required unsaturated amino acid amides, followed by resolution with an aminopeptidase present in Pseudomonas putida ATCC 12633 and/or a genetically modified organism, leading to the ( S )‐acids and ( R )‐amides. Undesired amino acid racemase activity was identified in the wild‐type strain, which was absent in the newly developed organism. The ( R )‐amides were hydrolyzed under mild conditions using an amidase present in whole cells from Rhodococcus erythropolis NCIMB 11540 to the ( R )‐acids. The viability of this procedure was demonstrated with the multi‐gram synthesis of a variety of unsaturated amino acids in excellent enantiopurity.