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Efficient Chemoenzymatic Synthesis of (2S,3R)-3-Hydroxy-3-Methylproline, a Key Fragment in Polyoxypeptin A and FR225659.

ABSTRACT: We report an efficient synthesis of protected (2S,3R)-3-hydroxy-3-methylproline that proceeds in three steps with complete stereoselectivity. This route represents a significant improvement over previous approaches to this noncanonical amino acid. Key to this success is the development of a one-pot chemoenzymatic procedure for the preparation of (2S,3S)-3- methylproline from L-isoleucine. This work lays the foundation for future chemoenzymatic syntheses of polyoxypeptin A and FR225659.

SUBMITTER: Zhang X

PROVIDER: S-EPMC6934255 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Efficient Chemoenzymatic Synthesis of (2S,3R)-3-Hydroxy-3-Methylproline, a Key Fragment in Polyoxypeptin A and FR225659.

Zhang Xiao X Renata Hans H

Tetrahedron 20190405 24

We report an efficient synthesis of protected (2S,3R)-3-hydroxy-3-methylproline that proceeds in three steps with complete stereoselectivity. This route represents a significant improvement over previous approaches to this noncanonical amino acid. Key to this success is the development of a one-pot chemoenzymatic procedure for the preparation of (2S,3S)-3- methylproline from L-isoleucine. This work lays the foundation for future chemoenzymatic syntheses of polyoxypept ...[more]

PMID: 31885405

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