Highly efficient and versatile synthesis of isotopically labelled 1-deoxy-D-xylulose

被引：26

作者：

Piel, J ^{[1
]}

Boland, W ^{[1
]}

机构：

[1] UNIV BONN,KEKULE INST ORGAN CHEM & BIOCHEM,D-53121 BONN,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(97)01448-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and versatile synthesis of 1-deoxy-[4,4-H-2(2)]-D-xylulose 1b (= 1-deoxy-[4,4-H-2(2)]-D-threopentulose) from dimethyl 2,3-O-isopropylidene-D-tartrate in 31% overall yield is described. The synthetic protocol allows a flexible adaptation to other labelling patterns and isotopes. Labelled 1-deoxy-xylulose is of high value as a metabolic probe in biosynthetic studies towards terpenoids and prenylated compounds following the Rohmer pathway. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：6387 / 6390

页数：4

共 20 条

[1]

[Anonymous], ANGEW CHEM

[2] JASMONIC ACID AND CORONATIN INDUCE ODOR PRODUCTION IN PLANTS [J].

BOLAND, W ;

HOPKE, J ;

DONATH, J ;

NUSKE, J ;

BUBLITZ, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1600-1602

[3] THE BIOSYNTHESIS OF THIAMINE - SYNTHESES OF [1,1,1,5-(H4)-H-2]-1-DEOXY-D-THREO-2-PENTULOSE AND INCORPORATION OF THIS SUGAR IN BIOSYNTHESIS OF THIAZOLE BY ESCHERICHIA-COLI-CELLS [J].

DAVID, S ;

ESTRAMAREIX, B ;

FISCHER, JC ;

THERISOD, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2131-2137

[4] Studies on the biosynthesis of taxol: The taxane carbon skeleton is not of mevalonoid origin [J].

Eisenreich, W ;

Menhard, B ;

Hylands, PJ ;

Zenk, MH ;

Bacher, A .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (13) :6431-6436

[5] PROKARYOTIC HOPANOIDS - THE BIOSYNTHESIS OF THE BACTERIOHOPANE SKELETON - FORMATION OF ISOPRENIC UNITS FROM 2 DISTINCT ACETATE POOLS AND A NOVEL TYPE OF CARBON CARBON LINKAGE BETWEEN A TRITERPENE AND D-RIBOSE [J].

FLESCH, G ;

ROHMER, M .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1988, 175 (02) :405-411

[6] BIOSYNTHESIS OF VITAMIN-B6 - INCORPORATION OF D-1-DEOXYXYLULOSE [J].

HILL, RE ;

SAYER, BG ;

SPENSER, ID .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1916-1917

[7] L-GALACTOSACCHARINIC ACIDS - NEW SACCHARINIC ACIDS FORMED BY CALCIUM HYDROXIDE TREATMENT OF L-SORBOSE [J].

ISHIZU, A ;

YOSHIDA, K ;

YAMAZAKI, N .

CARBOHYDRATE RESEARCH, 1972, 23 (01) :23-&

[8] 1-DEOXY-D-XYLULOSE [J].

KENNEDY, IA ;

HEMSCHEIDT, T ;

BRITTEN, JF ;

SPENSER, ID .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (08) :1329-1337

[9] Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway [J].

Lichtenthaler, HK ;

Schwender, J ;

Disch, A ;

Rohmer, M .

FEBS LETTERS, 1997, 400 (03) :271-274

[10]

MORIMOTO Y, 1987, CHEM PHARM BULL, V35, P2266

← 1 2 →