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Modular Enzymatic Cascade Synthesis of Vitamin B5 and Its Derivatives.

ABSTRACT: Access to vitamin B5 [(R)-pantothenic acid] and both diastereoisomers of ?-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-?-decarboxylase (ADC), ?-methylaspartate-?-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 ?-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 ?-alanine moiety.

SUBMITTER: Abidin MZ 

PROVIDER: S-EPMC6471175 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Modular Enzymatic Cascade Synthesis of Vitamin B<sub>5</sub> and Its Derivatives.

Abidin Mohammad Z MZ   Saravanan Thangavelu T   Zhang Jielin J   Tepper Pieter G PG   Strauss Erick E   Poelarends Gerrit J GJ  

Chemistry (Weinheim an der Bergstrasse, Germany) 20181030 66

Access to vitamin B<sub>5</sub> [(R)-pantothenic acid] and both diastereoisomers of α-methyl-substituted vitamin B<sub>5</sub> [(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-chira  ...[more]

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