Clarifying the structure of granadaene: Total synthesis of related analogue [2]-granadaene and confirmation of its absolute stereochemistry

被引：8

作者：

Paradas, Miguel ^{[1
]}

Jurado, Rocio ^{[1
]}

Haidour, Ali ^{[1
]}

Rodriguez Granger, Javier ^{[2
]}

Sampedro Martinez, Antonio ^{[2
]}

de la Rosa Fraile, Manuel ^{[2
]}

Robles, Rafael ^{[1
]}

Justicia, Jose ^{[1
]}

Cuerva, Juan M. ^{[1
]}

机构：

[1] Univ Granada, Fac Sci, Dept Organ Chem, E-18071 Granada, Spain

[2] Univ Hosp Virgen Nieves, Microbiol Serv, Granada 18014, Spain

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2012年 / 20卷 / 22期

关键词：

Natural product; Granadaene; Modular synthesis; Absolute stereochemistry; Structure; STREPTOCOCCUS-AGALACTIAE; CARBANIONS;

D O I：

10.1016/j.bmc.2012.09.017

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Streptococcus agalactiae is an important agent in the infection of neonates in the first world. One of the most extended methods for its identification is based on the detection of a characteristic red pigment in the patient samples, named [12]-granadaene (1). In this article, we present a modular and flexible approach to simple analogues of this ornithine rhamno-polyene 1 and the elucidation of the most important features of its structure: the absolute configuration at C-27, the stereochemistry of the anomeric center and the link of the amino acid ornithine to the rest of the structure. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6655 / 6661

页数：7

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