Total synthesis and stereochemical reassignment of tasiamide B.
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.
Sun
Tiantian
T
School of Pharmacy, Ocean University of China, Yushan Rd. 5, Qingdao, China.
Zhang
Wei
W
Zong
Chengli
C
Wang
Peng
P
Li
Yingxia
Y
D000596:Amino Acids / Q000737:chemistry; D000458:Cyanobacteria / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D009842:Oligopeptides; C480062:tasiamide B; C049986:4-amino-3-hydroxy-5-phenylpentanoic acid