Total synthesis and stereochemical reassignment of tasiamide.
The total synthesis of a marine acyclic peptide tasiamide and three diastereomers was reported for the first time. The synthesis has led to a reassignment of the N(alpha)-Me-L-Gln of tasiamide to be N(alpha)-Me-D-Gln, which was supported by 1H NMR, 13C NMR, COSY, HMQC, HMBC, and optical rotation.
Ma
Zhen-Hua
ZH
Key laboratory of Marine Drugs, the Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, China.
Song
Ni
N
Li
Chun-Xia
CX
Zhang
Wei
W
Wang
Peng
P
Li
Ying-Xia
YX
D000458:Cyanobacteria / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D009842:Oligopeptides; C470799:tasiamide