Stereochemistry of hydrogen introduction at C-25 in ergosterol synthesized by the mevalonate-independent pathway

被引：25

作者：

Zhou, WX ^{[1
]}

Nes, WD ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 16期

关键词：

biosynthesis; non-mevalonate pathway; Prototheca wickerhamii; ergosterol;

D O I：

10.1016/S0040-4039(00)00265-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Feeding of [1-C-13]glucose to Prototheca wickerhamii followed by C-13 NMR analysis of the resulting C-13-labeled ergosterol demonstrated this yeast-like al,aa operates the mevalonate-independent pathway. Based on the C-13 NMR signal assignment of [2,6,11,12,16,18,19, 21,23,27-C-13(10)] egosterol synthesized from [1-C-13]glucose indicated the pro-Z methyl group of cycloartenol is derived from C-5 of IPP and that protonation at C-25 of the Delta(25(27))-sterol intermediate takes place from the Si-face of Delta(25) to form the isopropyl pro-R methyl group. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2791 / 2795

页数：5

共 20 条

[1]

Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement [J].

Arigoni, D ;

Sagner, S ;

Latzel, C ;

Eisenreich, W ;

Bacher, A ;

Zenk, MH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (20) :10600-10605

[2]

SYNTHESIS OF 24-METHYL STEROLS STEREOSPECIFICALLY LABELED WITH H-2 IN THE ISOPROPYL METHYL-GROUPS - C-13 NMR SPECTRAL ASSIGNMENT OF C-26 AND C-27 RESONANCES [J].

COLOMBO, D ;

RONCHETTI, F ;

RUSSO, G ;

TOMA, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (03) :263-264

[3]

Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathways for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis PCC 6714 [J].

Disch, A ;

Schwender, J ;

Müller, C ;

Lichtenthaler, HK ;

Rohmer, M .

BIOCHEMICAL JOURNAL, 1998, 333 :381-388

[4]

DEVELOPMENTAL REGULATION OF STEROL BIOSYNTHESIS IN ZEA-MAYS [J].

GUO, DA ;

VENKATRAMESH, M ;

NES, WD .

LIPIDS, 1995, 30 (03) :203-219

[5]

Stereochemistry of hydrogen migration from C-24 to C-25 during phytosterol biomethylation [J].

Guo, DA ;

Jia, ZH ;

Nes, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (35) :8507-8508

[6]

Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs [J].

Jomaa, H ;

Wiesner, J ;

Sanderbrand, S ;

Altincicek, B ;

Weidemeyer, C ;

Hintz, M ;

Türbachova, I ;

Eberl, M ;

Zeidler, J ;

Lichtenthaler, HK ;

Soldati, D ;

Beck, E .

SCIENCE, 1999, 285 (5433) :1573-1576

[7]

MANGLA AT, 2000, IN PRESS BIOORG MED

[8]

NAGONO M, 1997, CHEM PHARM BULL, V45, P944

[9]

9β,19-cyclosterol analysis by 1H and 13C NMR, crystallographic observations, and molecular mechanics calculations [J].

Nes, WD ;

Koike, K ;

Jia, ZH ;

Sakamoto, Y ;

Satou, T ;

Nikaido, T ;

Griffin, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) :5970-5980

[10]

NES WD, 1992, PHYTOCHEMISTRY, V31, P805, DOI 10.1016/0031-9422(92)80019-B

← 1 2 →