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Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation.

ABSTRACT: Feglymycin is a naturally occurring, anti-HIV and antimicrobial 13-mer peptide that includes highly racemizable 3,5-dihydroxyphenylglycines (Dpgs). Here we describe the total synthesis of feglymycin based on a linear/convergent hybrid approach. Our originally developed micro-flow amide bond formation enabled highly racemizable peptide chain elongation based on a linear approach that was previously considered impossible. Our developed approach will enable the practical preparation of biologically active oligopeptides that contain highly racemizable amino acids, which are attractive drug candidates.

SUBMITTER: Fuse S

PROVIDER: S-EPMC5133696 | biostudies-other | 2016 Nov

REPOSITORIES: biostudies-other

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Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation.

Fuse Shinichiro S Mifune Yuto Y Nakamura Hiroyuki H Tanaka Hiroshi H

Nature communications 20161128

Feglymycin is a naturally occurring, anti-HIV and antimicrobial 13-mer peptide that includes highly racemizable 3,5-dihydroxyphenylglycines (Dpgs). Here we describe the total synthesis of feglymycin based on a linear/convergent hybrid approach. Our originally developed micro-flow amide bond formation enabled highly racemizable peptide chain elongation based on a linear approach that was previously considered impossible. Our developed approach will enable the practical preparation of biologically ...[more]

PMID: 27892469

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