title: Total synthesis and stereochemical reassignment of tasiamide B.
abstract: The first total synthesis of tasiamide B, an octapeptide bearing 4-amino-3-hydroxy-5-phenylpentanoic acid unit isolated from the marine cyanobacteria Symploca sp. is described. A simple and efficient way was found to avoid the pyroglutamylation of N(alpha)-Me-Gln and led to a reassignment of the N(alpha)-Me-L-Phe of tasiamide B to be N(alpha)-Me-D-Phe, which was also supported by 1D and 2D NMR.
authors.affiliation: School of Pharmacy, Ocean University of China, Yushan Rd. 5, Qingdao, China.
authors.forename: Tiantian
authors.initials: T
authors.lastname: Sun
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Chengli
authors.initials: C
authors.lastname: Zong
authors.forename: Peng
authors.initials: P
authors.lastname: Wang
authors.forename: Yingxia
authors.initials: Y
authors.lastname: Li
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D000458:Cyanobacteria / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D009842:Oligopeptides; C480062:tasiamide B; C049986:4-amino-3-hydroxy-5-phenylpentanoic acid