PREPARATION OF 1-THIOGLYCOSIDES HAVING OMEGA-ALDEHYDO AGLYCONS USEFUL FOR ATTACHMENT TO PROTEINS BY REDUCTIVE AMINATION

被引:25
作者
LEE, RT
LEE, YC
机构
[1] JOHNS HOPKINS UNIV,DEPT BIOL,BALTIMORE,MD 21218
[2] JOHNS HOPKINS UNIV,MCCOLLUM PRATT INST,BALTIMORE,MD 21218
关键词
D O I
10.1016/S0008-6215(00)83801-X
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 series of 1-thioglycosides containing an ω-aldehydo group (as the dimethyl acetal) on the aglycon were prepared by reaction of O-acetyl-1-thioaldoses with N-(chloroacetyl)aminoacetaldehyde dimethyl acetal, a compound readily prepared by the action of chloroacetyl chloride or chloroacetic anhydride on 2-aminoacetaldehyde dimethyl acetal. O-Deacetylation of the 1-thioglycosides, followed by deacetalation, yielded the desired products. An analogous 1-thioglycoside having a longer aglycon was prepared by reaction of 1-thio-D-galactose with (6-aminohexanoyl)-aminoacetaldehyde dimethyl acetal, obtained by condensing 6-bromohexanoic acid and aminoacetaldehyde with 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide. These glycosides were found to be useful for modification of proteins to yield neoglyco-proteins. © 1979.
引用
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页码:149 / 156
页数:8
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