title: Improved Synthesis of the Unnatural Amino Acids AHMOD and AMD, Components of the Anticancer Peptaibol Culicinin D.
abstract: An improved second-generation synthesis of the unnatural amino acid components of the anticancer peptaibol culicinin D has been developed. With a protected glutamic acid derivate as the starting material, the process readily delivered the Fmoc-protected free acid derivatives of AHMOD ((2S)-amino-(6R)-hydroxy-(4S)-methyl-8-oxodecanoic acid) and AMD ((2S)-amino-(4S)-methyldecanoic acid) required to support solid phase peptide synthesis (SPPS) for structure-activity studies of the natural product. The same approach also provides improved access to pipecolic acid derivatives. A novel Wittig reagent for one-carbon homologation of aldehydes, developed during this work, is also reported.
authors.affiliation: Maurice Wilkins Centre for Molecular Biodiscovery. School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
authors.forename: Kwang-Yoon
authors.initials: KY
authors.lastname: Ko
authors.affiliation: Maurice Wilkins Centre for Molecular Biodiscovery. School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
authors.forename: Sarah
authors.initials: S
authors.lastname: Wagner
authors.affiliation: Maurice Wilkins Centre for Molecular Biodiscovery. School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
authors.forename: Sung-Hyun
authors.initials: SH
authors.lastname: Yang
authors.affiliation: Maurice Wilkins Centre for Molecular Biodiscovery. School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Furkert
authors.affiliation: Maurice Wilkins Centre for Molecular Biodiscovery. School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry* / Q000494:pharmacology*; D054848:Peptaibols / Q000737:chemistry* / Q000494:pharmacology*; D060327:Solid-Phase Synthesis Techniques; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D000970:Antineoplastic Agents; D009842:Oligopeptides; D054848:Peptaibols; C511568:culicinin D