title: 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.
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.
authors.forename: Shinichiro
authors.initials: S
authors.lastname: Fuse
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.
authors.forename: Yuto
authors.initials: Y
authors.lastname: Mifune
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Nakamura
authors.affiliation: Department of Chemical Science and Engineering, School of Material and Chemical Technology, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tanaka
mesh_terms: D000577:Amides / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry; D010455:Peptides; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D012212:Rheology
chemical_list: D000577:Amides; D009842:Oligopeptides; D010455:Peptides; D011506:Proteins; C120179:feglymycin; D005998:Glycine