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

Shinichiro Fuse (), Yuto Mifune, Hiroyuki Nakamura and Hiroshi Tanaka
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Shinichiro Fuse: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Yuto Mifune: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Hiroyuki Nakamura: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Hiroshi Tanaka: School of Material and Chemical Technology, Tokyo Institute of Technology

Nature Communications, 2016, vol. 7, issue 1, 1-7

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms13491

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