Biosynthesis of thiamin thiazole: Determination of the regiochemistry of the S/O acyl shift by using 1,4-dideoxy-D-xylulose-5-phosphate

被引:7
作者
Chatterjee, Abhishek [1 ]
Han, Xuemei [1 ]
McLafferty, Fred W. [1 ]
Begley, Tadhg P. [1 ]
机构
[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
关键词
acyl shift; biosynthesis; enzyme catalysis; isotopic labeling; vitamins;
D O I
10.1002/anie.200504614
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) ThiS and that: An alternative substrate for thiazole synthase, namely 1,4-dideoxy-D-xylulose-5-phosphate, was synthesized and used as a mechanistic probe to determine the regiochemistry of the acyl-shift reaction that occurs as an intermediate step in the biosynthesis of thiamin thiazole in B. subtilis (see scheme; ThiS protein (blue); ThiG protein (red); OP=phosphate group). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3507 / 3510
页数:4
相关论文
共 23 条
[1]   ANTIBIOTIC 1233A - FUNGAL BETA LACTONE [J].
ALDRIDGE, DC ;
GILES, D ;
TURNER, WB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (23) :3888-&
[2]   β-Lactam synthetase:: A new biosynthetic enzyme [J].
Bachmann, BO ;
Li, RF ;
Townsend, CA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (16) :9082-9086
[3]   Thiamin biosynthesis in prokaryotes [J].
Begley, TP ;
Downs, DM ;
Ealick, SE ;
McLafferty, FW ;
Van Loon, APGM ;
Taylor, S ;
Campobasso, N ;
Chiu, HJ ;
Kinsland, C ;
Reddick, JJ ;
Xi, J .
ARCHIVES OF MICROBIOLOGY, 1999, 171 (05) :293-300
[4]   The biosynthesis and degradation of thiamin (Vitamin B-1) [J].
Begley, TP .
NATURAL PRODUCT REPORTS, 1996, 13 (03) :177-185
[5]   FOURIER-TRANSFORM ELECTROSPRAY INSTRUMENTATION FOR TANDEM HIGH-RESOLUTION MASS-SPECTROMETRY OF LARGE MOLECULES [J].
BEU, SC ;
SENKO, MW ;
QUINN, JP ;
WAMPLER, FM ;
MCLAFFERTY, FW .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1993, 4 (07) :557-565
[6]   Thiamin deficiency and brain disorders [J].
Butterworth, RF .
NUTRITION RESEARCH REVIEWS, 2003, 16 (02) :277-283
[7]   Mechanistic studies on the inactivation of the proteasome by lactacystin A central role for clasto-lactacystin beta-lactone [J].
Dick, LR ;
Cruikshank, AA ;
Grenier, L ;
Melandri, FD ;
Nunes, SL ;
Stein, RL .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (13) :7273-7276
[8]   The biosynthesis of the thiazole phosphate moiety of thiamin: The sulfur transfer mediated by the sulfur carrier protein ThiS [J].
Dorrestein, PC ;
Zhai, HL ;
McLafferty, FW ;
Begley, TP .
CHEMISTRY & BIOLOGY, 2004, 11 (10) :1373-1381
[9]   The biosynthesis of the thiazole phosphate moiety of thiamin (Vitamin B1):: The early steps catalyzed by thiazole synthase [J].
Dorrestein, PC ;
Zhai, HL ;
Taylor, SV ;
McLafferty, FW ;
Begley, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3091-3096
[10]  
Estramareix B, 1996, NEW J CHEM, V20, P607