A Biocatalytic Route to Enantiomerically Pure Unsaturated [alpha]-H-[alpha]-Amino Acids

A set of both enantiomeric forms of non-proteinogenic, unsaturated [alpha]-H-[alpha]-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 pr...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2001-08, Vol.343 (6-7), p.662-674
Main Authors: Wolf, Larissa B, Sonke, Theo, Tjen, Kim CMF, Kaptein, Bernard, Broxterman, Quirinus B, Schoemaker, Hans E, Rutjes, Floris PJT
Format: Article
Language:English
Subjects:
Amidase
Amides
Amino acids
Organisms
Rhodococcus
Strain
Synthesis
Unsaturated
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Summary:A set of both enantiomeric forms of non-proteinogenic, unsaturated [alpha]-H-[alpha]-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.
ISSN:1615-4150
1615-4169
DOI:10.1002/1615-4169(200108)343:6/7<662::AID-ADSC662>3.0.CO;2-I