Chemical synthesis of uridine diphospho-D-Xylose and UDP-L-arabinose

被引:27
作者
Ernst, C
Klaffke, W
机构
[1] Unilever Hlth Inst, Unilever Res & Dev, NL-3130 AT Vlaardingen, Netherlands
[2] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
D O I
10.1021/jo034379u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Leloir transferases, like UDP-D-XyloSyl transferase and arabinosyl transferase, utilize nucleoside diphosphate sugars to build up plant oligo- and polysaccharides. By the described, scalable three-step synthesis a simple route is described to arrive at the respective enzyme substrates, which are otherwise difficult to obtain.
引用
收藏
页码:5780 / 5783
页数:4
相关论文
共 13 条
[1]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[2]   RAPID CHEMICAL SYNTHESIS OF SUGAR NUCLEOTIDES IN A FORM SUITABLE FOR ENZYMATIC OLIGOSACCHARIDE SYNTHESIS [J].
ARLT, M ;
HINDSGAUL, O .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :14-15
[3]   FURTHER STUDIES ON MECHANISM OF ACTION OF UDP-APIOSE-UDP-XYLOSE SYNTHASE FROM CELL-CULTURES OF PARSLEY [J].
BARON, D ;
GRISEBAC.H .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1973, 38 (01) :153-159
[4]   A short route to nucleoside diphosphate activated D- and L-hexoses [J].
Ernst, C ;
Klaffke, W .
TETRAHEDRON LETTERS, 2001, 42 (16) :2973-2975
[5]   One-step, stereocontrolled synthesis of glycosyl 1-phosphates, uridine-5′-diphosphogalactose, and uridine-5′-diphosphoglucose from unprotected glycosyl donors [J].
Hanessian, S ;
Lu, PP ;
Ishida, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) :13296-13300
[6]   Plant glycosyltransferases [J].
Keegstra, K ;
Raikhel, N .
CURRENT OPINION IN PLANT BIOLOGY, 2001, 4 (03) :219-224
[7]   Enzymatic synthesis and purification of uridine diphospho-β-L-arabinopyranose, a substrate for the biosynthesis of plant polysaccharides [J].
Pauly, M ;
Porchia, A ;
Olsen, CE ;
Nunan, KJ ;
Scheller, HV .
ANALYTICAL BIOCHEMISTRY, 2000, 278 (01) :69-73
[8]   NUCLEOSIDE POLYPHOSPHATES .11. AN IMPROVED GENERAL METHOD FOR SYNTHESIS OF NUCLEOTIDE COENZYMES - SYNTHESES OF URIDINE-5', CYTIDINE-5' AND GUANOSINE-5' DIPHOSPHATE DERIVATIVES [J].
ROSEMAN, S ;
DISTLER, JJ ;
MOFFATT, JG ;
KHORANA, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (03) :659-&
[9]  
ROSS J, 2000, GENOME BIOL, V2
[10]   GLYCOSYLIMIDATES .53. DIRECT SYNTHESIS OF NUCLEOSIDE MONOPHOSPHATE SUGARS SYNTHESIS OF GMP-FUCOSE [J].
SCHMIDT, RR ;
BRAUN, H ;
JUNG, KH .
TETRAHEDRON LETTERS, 1992, 33 (12) :1585-1588