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Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
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Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
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Journal Article
Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation
2016
Overview
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.
Feglymycin is a biologically active peptide but a challenging synthetic target due to the highly racemizable nature of the 3,5-dihydroxyphenylglycine groups. Here the authors report the synthesis of feglymycin using a microflow system, allowing amide bond formation without severe racemization.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
