SYNTHESIS OF 2-DEOXY-ALPHA-D-ARABINO-HEXOPYRANOSYL PHOSPHATE AND 2-DEOXY-MALTOOLIGOSACCHARIDES WITH PHOSPHORYLASE

被引:31
作者
EVERS, B [1 ]
MISCHNICK, P [1 ]
THIEM, J [1 ]
机构
[1] UNIV HAMBURG,INST ORGAN CHEM,D-20146 HAMBURG,GERMANY
关键词
ENZYMATIC SYNTHESIS; PHOSPHORYLASE; 2-DEOXY-ALPHA-D-ARABINO-HEXOPYRANOSYL PHOSPHATE; 2-DEOXYAMYLOSE;
D O I
10.1016/0008-6215(94)84189-6
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A convenient one-step synthesis of 2-deoxy-alpha-D-arabino-hexopyranosyl phosphate on a millimolar scale is described by reaction of potato phosphorylase with D-glucal at equimolar phosphate concentration. Furthermore, in the presence of catalytic amounts of phosphate, a 2-deoxy-maltooligosaccharide is obtained from maltotetraose and D-glucal. The water,insoluble oligosaccharide was isolated and characterized by H-1 and C-13 NMR spectroscopy. An average dp of 20 was thus determined.
引用
收藏
页码:335 / 341
页数:7
相关论文
共 23 条
[1]  
Fiske CH, 1925, J BIOL CHEM, V66, P375
[2]   PRIMER SPECIFICITY OF POTATO PHOSPHORYLASE [J].
FRENCH, D ;
WILD, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (18) :4490-4492
[3]   OLIGOSACCHARIDE CONFORMATION AND PROTEIN SACCHARIDE INTERACTIONS IN SOLUTION [J].
GOLDSMITH, E ;
FLETTERICK, RJ .
PURE AND APPLIED CHEMISTRY, 1983, 55 (04) :577-588
[4]   SYNTHESIS OF LAMINARIOLIGOSACCHARIDES USING CRUDE EXTRACT OF EUGLENA-GRACILIS Z-CELLS [J].
KITAOKA, M ;
SASAKI, T ;
TANIGUCHI, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (05) :1431-1432
[5]   GENERAL ACID-BASE CATALYSIS OF ALPHA-GLUCAN PHOSPHORYLASES - STEREOSPECIFIC GLUCOSYL TRANSFER FROM D-GLUCAL IS A PYRIDOXAL 5'-PHOSPHATE AND ORTHO-PHOSPHATE (ARSENATE) DEPENDENT REACTION [J].
KLEIN, HW ;
PALM, D ;
HELMREICH, EJM .
BIOCHEMISTRY, 1982, 21 (26) :6675-6684
[7]   NEW ROUTE TO GLYCOSYL PHOSPHATES [J].
MACDONALD, DK .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :1107-&
[8]  
MISCHNICK P, IN PRESS CARBOYDR RE
[9]   SYNTHETIC APPROACHES TO 2-DEOXYGLYCOSYL PHOSPHATES [J].
NIGGEMANN, J ;
LINDHORST, TK ;
WALFORT, M ;
LAUPICHLER, L ;
SAJUS, H ;
THIEM, J .
CARBOHYDRATE RESEARCH, 1993, 246 :173-183
[10]   THE ROLE OF PYRIDOXAL 5'-PHOSPHATE IN GLYCOGEN-PHOSPHORYLASE CATALYSIS [J].
PALM, D ;
KLEIN, HW ;
SCHINZEL, R ;
BUEHNER, M ;
HELMREICH, EJM .
BIOCHEMISTRY, 1990, 29 (05) :1099-1107