title: An improved synthesis of (2S, 4S)- and (2S, 4R)-2-amino-4-methyldecanoic acids: assignment of the stereochemistry of culicinins.
abstract: An improved synthesis of (2S, 4S)- and (2S, 4R)-2-amino-4-methyldecanoic acids was accomplished using a glutamate derivative as starting material and Evans' asymmetric alkylation as the decisive step. The NMR data of the two diastereomers were measured and compared with those of the natural product. As a result, the stereochemistry of this novel amino acid unit in culicinins was assigned as (2S, 4R).
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Ning
authors.initials: N
authors.lastname: Ding
authors.forename: Yingxia
authors.initials: Y
authors.lastname: Li
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003652:Decanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018698:Glutamic Acid / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D054848:Peptaibols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003652:Decanoic Acids; D054848:Peptaibols; D018698:Glutamic Acid