✦ LIBER ✦

Total synthesis and stereochemical reassignment of tasiamide B

✍ Scribed by Tiantian Sun; Wei Zhang; Chengli Zong; Peng Wang; Yingxia Li

Book ID: 105359883
Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 287 KB
Volume: 16
Category: Article
ISSN: 1075-2617
DOI: 10.1002/psc.1254

No coin nor oath required. For personal study only.

✦ Synopsis

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^α^‐Me‐Gln and led to a reassignment of the N^α^‐Me‐L‐Phe of tasiamide B to be N^α^‐Me‐D‐Phe, which was also supported by 1D and 2D NMR. Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd.

📜 SIMILAR VOLUMES

Total synthesis and stereochemical reass

Total synthesis and stereochemical reassignment of tasiamide

✍ Zhen-Hua Ma; Ni Song; Chun-Xia Li; Wei Zhang; Peng Wang; Ying-Xia Li 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 English ⚖ 180 KB

## Abstract 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__^α^‐Me‐L‐Gln of tasiamide to be __N__^α^‐Me‐D‐Gln, which was supported by ^1^H NMR, ^13^C NMR, COSY, HMQC, HMBC, and opt