CHEMOENZYMATIC SYNTHESIS OF PRECURSORS OF FAGOMINE AND 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL

被引:23
作者
HECQUET, L [1 ]
LEMAIRE, M [1 ]
BOLTE, J [1 ]
DEMUYNCK, C [1 ]
机构
[1] UNIV CLERMONT FERRAND,CNRS,CHIM ORGAN BIOL LAB,F-63177 CLERMONT FERRAND,FRANCE
关键词
D O I
10.1016/S0040-4039(00)78499-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselectivity of transketolase towards, alpha-hydroxy-aldehydes is used to prepare compounds bearing two asymmetric centres, precursors of natural products: 2,3-dideoxynojirimycine (fagomine), 1,4-dideoxy-1,4-imino-D-arabinitol, and its oxidised form.
引用
收藏
页码:8791 / 8794
页数:4
相关论文
共 30 条
[1]  
BERGMEYER HU, 1974, METHOD ENZYMAT AN, V3, P1452
[2]  
BOLTE J, 1987, TETRAHEDRON LETT, V28, P5025
[3]   POTENTIAL GLYCOSIDASE INHIBITORS - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO DERIVATIVES OF D-GLUCITOL, D-XYLITOL AND L-XYLITOL, D-ALLITOL AND L-ALLITOL, D-TALITOL AND L-TALITOL, AND D-GULITOL [J].
BUCHANAN, JG ;
LUMBARD, KW ;
STURGEON, RJ ;
THOMPSON, DK ;
WIGHTMAN, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :699-706
[4]  
CHEN SH, 1990, TETRAHEDRON LETT, V31, P2229
[5]   PREPARATION OF OPTICALLY PURE L-2-HYDROXYALDEHYDES WITH YEAST TRANSKETOLASE [J].
EFFENBERGER, F ;
NULL, V ;
ZIEGLER, T .
TETRAHEDRON LETTERS, 1992, 33 (36) :5157-5160
[6]   LACK OF GLYCOSIDASE INHIBITION BY, AND ISOLATION FROM XANTHOCERCIS-ZAMBESIACA (LEGUMINOSAE) OF, 4-0-(BETA-D-GLUCOPYRANOSYL)-FAGOMINE [1,2,5-TRIDEOXY-4-0-(BETA-D-GLUCOPYRANOSYL)-1,5-IMINO-D-ARABINO-HEXITOL], A NOVEL GLUCOSIDE OF A POLYHYDROXYLATED PIPERIDINE ALKALOID [J].
EVANS, SV ;
HAYMAN, AR ;
FELLOWS, LE ;
SHING, TKM ;
DEROME, AE ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1985, 26 (11) :1465-1468
[7]   GLYCOSIDASE INHIBITION BY PLANT ALKALOIDS WHICH ARE STRUCTURAL ANALOGS OF MONOSACCHARIDES [J].
EVANS, SV ;
FELLOWS, LE ;
SHING, TKM ;
FLEET, GWJ .
PHYTOCHEMISTRY, 1985, 24 (09) :1953-1955
[8]  
FELLOWS LL, 1987, CHEM BR, V27, P842
[9]   ENANTIOSPECIFIC SYNTHESES OF DEOXYMANNOJIRIMYCIN, FAGOMINE AND 2R,5R-DIHYDROXYMETHYL-3R,4R-DIHYDROXYPYRROLIDINE FROM D-GLUCOSE [J].
FLEET, GWJ ;
SMITH, PW .
TETRAHEDRON LETTERS, 1985, 26 (11) :1469-1472
[10]   POTENT COMPETITIVE-INHIBITION OF ALPHA-GALACTOSIDASE AND ALPHA-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS - SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL [J].
FLEET, GWJ ;
NICHOLAS, SJ ;
SMITH, PW ;
EVANS, SV ;
FELLOWS, LE ;
NASH, RJ .
TETRAHEDRON LETTERS, 1985, 26 (26) :3127-3130