A facile Fmoc solid phase synthesis strategy to access epimerization-prone biosynthetic intermediates of glycopeptide antibiotics

Clara Brieke, Max J Cryle

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45 Citations (Scopus)

Abstract

A rapid protocol based on Fmoc-chemistry for the solid phase peptide synthesis of vancomycin- and teicoplanin-type peptides is described. Epimerization of highly racemization-prone arlyglycine derivatives is suppressed through optimized Fmoc-deprotection and coupling conditions. Starting from easily accessible Fmoc-protected amino acids, this strategy enables the enantioselective synthesis of peptides corresponding to intermediates found in vancomycin and teicoplanin biosynthesis with excellent purity and in high yields (38 -71 ).
Original languageEnglish
Pages (from-to)2454-2457
Number of pages4
JournalOrganic Letters
Volume16
Issue number9
DOIs
Publication statusPublished - 14 Apr 2014
Externally publishedYes

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