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- Title
Modular Enzymatic Cascade Synthesis of Vitamin B<sub>5</sub> and Its Derivatives.
- Authors
Abidin, Mohammad Z.; Saravanan, Thangavelu; Zhang, Jielin; Tepper, Pieter G.; Poelarends, Gerrit J.; Strauss, Erick
- Abstract
Access to vitamin B5 [(R)‐pantothenic acid] and both diastereoisomers of α‐methyl‐substituted vitamin B5 [(R)‐ and (S)‐3‐((R)‐2,4‐dihydroxy‐3,3‐dimethylbutanamido)‐2‐methylpropanoic acid] was achieved using a modular three‐step biocatalytic cascade involving 3‐methylaspartate ammonia lyase (MAL), aspartate‐α‐decarboxylase (ADC), β‐methylaspartate‐α‐decarboxylase (CrpG) or glutamate decarboxylase (GAD), and pantothenate synthetase (PS) enzymes. Starting from simple non‐chiral dicarboxylic acids (either fumaric acid or mesaconic acid), vitamin B5 and both diastereoisomers of α‐methyl‐substituted vitamin B5, which are valuable precursors for promising antimicrobials against Plasmodium falciparum and multidrug‐resistant Staphylococcus aureus, can be generated in good yields (up to 70 %) and excellent enantiopurity (>99 % ee). This newly developed cascade process may be tailored and used for the biocatalytic production of various vitamin B5 derivatives by modifying the pantoyl or β‐alanine moiety. Unity in diversity: Starting from simple non‐chiral dicarboxylic acids, enantiopure vitamin B5 derivatives, which are valuable antimicrobial precursors, were prepared using a modular reaction cascade involving three different enzymes in one‐pot.
- Subjects
PANTOTHENIC acid; BIOCATALYSIS; METHYL aspartate; DIASTEREOISOMERS; PLASMODIUM falciparum
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 66, p17434
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201804151