INFLUENCE OF LIPOPHILIC N-ACYL DERIVATIVES OF D-GLUCOSAMINE IN THE GALACTOSYLATION WITH GALACTOSYLTRANSFERASE

被引:0
作者
ATS, SC [1 ]
LEHMANN, J [1 ]
机构
[1] UNIV FREIBURG,INST ORGAN CHEM & BIOCHEM,D-79104 FREIBURG,GERMANY
来源
LIEBIGS ANNALEN DER CHEMIE | 1994年 / 09期
关键词
BETA-GALACTOSYLTRANSFERASE; ENZYMES; CARBOHYDRATES;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several D-glucosamine derivatives varying in N-acylation were used as acceptor substrates for galactosyltransferase and the relative rates of their galactosylation by UDP-Gal measured. One of them, 2-deoxy-2-[4-(2-indolyl)butyramido]-D-glucose (6) was newly synthesised and galactosylated at a significantly enhanced rate (14 times) in competition with GlcNAc as standard. Generally an increased lipophilicity increases the relative rate, provided the N-acyl group in question does not sterically hinder acceptor binding because it increases the bulk of the pyranose ring system.
引用
收藏
页码:951 / 953
页数:3
相关论文
共 18 条
[1]   SPACER-MODIFIED TRISACCHARIDE GLYCOSIDES THAT MIMIC THE BIANTENNARY ASN-LINKED OLIGOSACCHARIDE ACCEPTOR OF (1-]4)-BETA-D-GALACTOSYLTRANSFERASE AND CAN BE USED AS COMPETITIVE INHIBITORS AND FOR IRREVERSIBLE DEACTIVATION [J].
ATS, SC ;
LEHMANN, J ;
PETRY, S .
CARBOHYDRATE RESEARCH, 1992, 233 :141-150
[2]  
BAHL OP, 1992, GLYCOCONJUGATES COMP, P1
[3]  
COOK GMW, 1973, SURFACE CARBOHYDRATE, P56
[4]   HYDROPHOBIC CHROMATOGRAPHY OF GALACTOSYLTRANSFERASE [J].
GEREN, CR ;
MAGEE, SC ;
EBNER, KE .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1976, 172 (01) :149-155
[5]  
GREEN CR, 1976, ARCH BIOCHEM BIOPHYS, V172, P149
[6]  
KAYSER H, 1992, J BIOL CHEM, V267, P16934
[7]   NEW AMINO SUGAR ANALOGS ARE INCORPORATED AT DIFFERENT RATES INTO GLYCOPROTEINS OF MOUSE ORGANS [J].
KAYSER, H ;
ATS, C ;
LEHMANN, J ;
REUTTER, W .
EXPERIENTIA, 1993, 49 (10) :885-887
[8]  
LUKIN OV, 1976, J ORG CHEM USSR, V12, P556
[9]   CONTROL OF GLYCOPROTEIN-SYNTHESIS - SUBSTRATE-SPECIFICITY OF RAT-LIVER UDP-GLCNAC-MAN ALPHA-3R BETA-2-N-ACETYLGLUCOSAMINYL-TRANSFERASE-I USING SYNTHETIC SUBSTRATE-ANALOGS [J].
MOLLER, G ;
RECK, F ;
PAULSEN, H ;
KAUR, KJ ;
SARKAR, M ;
SCHACHTER, H ;
BROCKHAUSEN, I .
GLYCOCONJUGATE JOURNAL, 1992, 9 (04) :180-190
[10]   GALACTOSYLATION OF NONNATURAL GLYCOSIDES WITH HUMAN BETA-D-GALACTOSYLTRANSFERASE ON A PREPARATIVE SCALE [J].
OHRLEIN, R ;
ERNST, B ;
BERGER, EG .
CARBOHYDRATE RESEARCH, 1992, 236 :335-338