Solid-phase synthesis of a putative heptapeptide intermediate in vancomycin biosynthesis

Abstract

The solid-phase synthesis was completed of the heptapeptide D-Leu-D-Tyr-L-Asn-Hpg-Hpg-L-Tyr-Dhpg, a putative intermediate in vancomycin biosynthesis, where Dhpg = (S)-3,5-dihydroxyphenylglycine and Hpg = (R)-4-hydroxyphenylglycine, using 2-chlorotrityl resin, benzyl side-chain protecting groups for the aromatic residues, and Alloc chemistry for chain elongation; the heptapeptide was obtained in 16% yield with the correct relative and absolute configuration.