title: Total Synthesis and Stereochemical Assignment of the Antimicrobial Lipopeptide Cerexin A1.
abstract: The isolation and total synthesis of the antimicrobial lipopeptide cerexin A1 is reported. This synthesis includes the preparation of orthogonally protected γ-hydroxylysine, utilizing a nitrile Reformatsky-type reaction as a key step to yield both diastereomers more efficiently than previously reported methods. The configuration of the β-hydroxyl in the lipid tail was determined by the use of a modified Ohrui-Akasaka approach. Furthermore, new cerexin analogues from Bacillus mycoides ATCC 21929 were isolated and characterized, revealing an ε-amino succinylation of a hydroxylysine residue that is unusual in a nonribosomal peptide synthetase product.
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Stephen A
authors.initials: SA
authors.lastname: Cochrane
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Richard R
authors.initials: RR
authors.lastname: Surgenor
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Kevin M W
authors.initials: KM
authors.lastname: Khey
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: John C
authors.initials: JC
authors.lastname: Vederas
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000890:Anti-Infective Agents; D023181:Antimicrobial Cationic Peptides; D001409:Bacillus cereus / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D023181:Antimicrobial Cationic Peptides; D010455:Peptides; C010069:cerexins