2-IMINO-2-METHOXYETHYL 1-THIOGLYCOSIDES - NEW REAGENTS FOR ATTACHING SUGARS TO PROTEINS
2-IMINO-2-METHOXYETHYL 1-THIOGLYCOSIDES - NEW REAGENTS FOR ATTACHING SUGARS TO PROTEINS
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DOI：
10.1021/bi00663a008
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发表时间：
1976-01-01
期刊：
影响因子：
2.9
通讯作者：
KRANTZ, MJ
中科院分区：
文献类型：
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作者：
LEE, YC;STOWELL, CP;KRANTZ, MJ
以假硫脲衍生物和氯乙腈为原料，分别合成了D-半乳糖、D-葡萄糖、2-乙酰氨基-2-脱氧-D-葡萄糖和D-甘露糖的氰甲基1-硫代糖苷。这些氰甲基硫代糖苷中的腈基可以通过用甲醇钠或HCl在无水甲醇中处理转化为亚氨酸甲酯基，得到2-亚氨基-2-甲氧基乙基1-硫代糖苷（IME-硫代糖苷）。考察了影响IME-硫代糖苷收率的因素。制备IME-硫代糖苷的最方便的方法是通过在室温下用0.01 M甲醇钠在无水甲醇中处理0.1 M氰基甲基硫代糖苷过乙酸酯24-48 h（50-60%产率）。这些IME-硫代糖苷在弱碱性缓冲溶液中容易与简单的胺、氨基酸和蛋白质反应。α-在适当的条件下，用这些试剂修饰的淀粉酶和溶菌酶保留了全部活性。因此，IME-硫代糖苷构成了一组新的用于将糖连接至蛋白质的试剂。
Cyanomethyl 1-thioglycosides of D-galactose, D-glucose, 2-acetamido-2-deoxy-D-glucose and D-mannose were prepared from the respective pseudothiourea derivatives and chloroacetonitrile. The nitrile group in these cyanomethyl thioglycosides can be converted to a methyl imidate group by treatment with sodium methoxide or HCl in dry methanol to yield 2-imino-2-methoxyethyl 1-thioglycosides (IME-thioglycosides). The factors influencing the yield of IME-thioglycosides were investigated. The most convenient method of preparing IME-thioglycosides was by treating 0.1 M cyanomethyl thioglycoside peracetate in dry methanol with 0.01 M sodium methoxide at room temperature for 24-48 h (50-60% yield). These IME-thioglycosides reacted readily with simple amines, amino acids and proteins in mildly alkaline buffer solutions. .alpha.-Amylase and lysozyme modified with these reagents under appropriate conditions retained full activities. Thus the IME-thioglycosides constitute a new group of reagents for attaching sugars to proteins.