title: A facile Fmoc solid phase synthesis strategy to access epimerization-prone biosynthetic intermediates of glycopeptide antibiotics.
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%).
authors.affiliation: Department of Biomolecular Mechanisms, Max-Planck Institute for Medical Research , Jahnstrasse 29, 69120 Heidelberg, Germany.
authors.forename: Clara
authors.initials: C
authors.lastname: Brieke
authors.forename: Max J
authors.initials: MJ
authors.lastname: Cryle
mesh_terms: D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D060327:Solid-Phase Synthesis Techniques; D013237:Stereoisomerism; D017334:Teicoplanin / Q000138:chemical synthesis* / Q000737:chemistry; D014640:Vancomycin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D006020:Glycopeptides; D017334:Teicoplanin; D014640:Vancomycin