title: Synthesis of the peptaibol framework of the anticancer agent culicinin D: stereochemical assignment of the AHMOD moiety.
abstract: The postulated structure of the potent anticancer peptaibol culicinin D has been synthesized using Fmoc-based solid-phase peptide synthesis (SPPS). Comparison of the (1)H NMR data for the reported structure of culicinin D with the data obtained for the two synthetic polypeptides epimeric at C-6 in the AHMOD unit established the C-6 stereochemistry of the AHMOD residue in the natural product to be (R).
authors.affiliation: School of Chemical Sciences and The Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors.forename: Kuo-yuan
authors.initials: KY
authors.lastname: Hung
authors.forename: Paul W R
authors.initials: PW
authors.lastname: Harris
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D054848:Peptaibols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000970:Antineoplastic Agents; D009842:Oligopeptides; D054848:Peptaibols; D010455:Peptides; C511568:culicinin D