通过全合成将西米兰酰胺结构修饰为PF1171C。

Structure Revision of Similanamide to PF1171C by Total Synthesis.

作者信息

Masuda Yuichi, Tanaka Ren, Ganesan A, Doi Takayuki

机构信息

Graduate School of Pharmaceutical Sciences, Tohoku University , 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai, Miyagi 980-8578, Japan.

School of Pharmacy, University of East Anglia , Norwich Research Park, Norwich NR4 7TJ, United Kingdom.

出版信息

J Nat Prod. 2015 Sep 25;78(9):2286-91. doi: 10.1021/acs.jnatprod.5b00643. Epub 2015 Sep 8.

DOI:10.1021/acs.jnatprod.5b00643

PMID:26348363

Abstract

The total synthesis of the proposed structure of similanamide, a cyclic hexapeptide recently isolated from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013, was achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The NMR spectra of our synthetic final product were not identical to those of the isolated material and led us to conclude that similanamide is identical to PF1171C, a previously reported diastereomeric hexapeptide.

摘要

西米兰酰胺是一种最近从与海洋海绵相关的真菌西米兰曲霉KUFA 0013中分离出的环状六肽，通过线性前体的固相合成和溶液相大环内酰胺化实现了其提议结构的全合成。我们合成的最终产物的核磁共振谱与分离出的物质的谱图不同，这使我们得出结论，西米兰酰胺与之前报道的非对映体六肽PF1171C相同。