从链霉菌菌株MJ858-NF3中分离并合成新型法尼基蛋白转移酶抑制剂瓦利诺菌素A和B。

Isolation and synthesis of novel farnesyl protein transferase inhibitors, valinoctins A and B, from Streptomyces strain MJ858-NF3.

作者信息

Sekizawa R, Iinuma H, Muraoka Y, Naganawa H, Kinoshita N, Nakamura H, Hamada M, Takeuchi T, Umezawa K

机构信息

Department of Applied Chemistry, Keio University, Kanagawa, Japan.

出版信息

J Nat Prod. 1996 Mar;59(3):232-6. doi: 10.1021/np960067t.

DOI:10.1021/np960067t

PMID:8882425

Abstract

Two novel farnesyl protein transferase inhibitors, valinoctins A (1) and B (2), were isolated from the fermentation broth of Streptomyces strain MJ858-NF3. The tentative structures of these compounds were elucidated from NMR and mass spectra as dipeptides consisting of valine and a novel amino acyl moiety. Four possible isomers of valinoctin A were synthesized, and the protected derivative of the appropriate compound was crystallized to give the relative stereochemistry of X-ray analysis. Since the valine residue of valinoctin A was determined to be the L-configuration by a chiral HPLC column, absolute configuration of valinoctin A was determined.

摘要

从链霉菌菌株MJ858-NF3的发酵液中分离出两种新型法尼基蛋白转移酶抑制剂，缬氨酸辛A（1）和缬氨酸辛B（2）。通过核磁共振和质谱将这些化合物的暂定结构阐明为由缬氨酸和一种新型氨基酰基部分组成的二肽。合成了缬氨酸辛A的四种可能异构体，并使合适化合物的保护衍生物结晶以给出X射线分析的相对立体化学。由于通过手性高效液相色谱柱确定缬氨酸辛A的缬氨酸残基为L-构型，因此确定了缬氨酸辛A的绝对构型。