SYNTHESIS OF REGIOISOMERIC METHYL ALPHA-L-ARABINOFURANOBIOSIDES

被引:40
作者
KAWABATA, Y
KANEKO, S
KUSAKABE, I
GAMA, Y
机构
[1] UNIV TSUKUBA,INST APPL BIOCHEM,TSUKUBA,IBARAKI 305,JAPAN
[2] NATL INST MAT & CHEM RES,TSUKUBA,IBARAKI 305,JAPAN
关键词
REGIOISOMERIC; ARABINOFURANOBIOSIDES; METHYL ALPHA-L-;
D O I
10.1016/0008-6215(94)00290-V
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
The three regioisomers of methyl alpha-L-arabinofuranobioside, namely methyl O-alpha-L-arabinofuranosyl-(1-->2)-alpha-L-arabinofuranoside, methyl O-alpha-L-arabinofuranosyl-(1-->3)-alpha-L-arabinofuranoside, and methyl O-alpha-L-arabinofuranosyl-(1-->5)-alpha-L-arabinofuranoside, were synthesized for use as substrates in studies of the specificity of alpha-L-arabinofuranosidase. The regiospecifically protected precursors, namely methyl 3,5-di-O-benzoyl-alpha-L-arabinofuranoside, methyl 2,5-di-O-benzyl-alpha-L-arabinofuranoside, and methyl 2,3-di-O-benzoyl-alpha-L-arabinofuranoside, were prepared from 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl chloride (4) and methyl 5-O-trityl-alpha-L-arabinofuranoside, respectively, and glycosylated with 4 in the presence of silver trifluoromethanesulfonate and s-collidine. H-1 and C-13 NMR data for all compounds are presented.
引用
收藏
页码:39 / 47
页数:9
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