Preparation of some new neoglycoproteins by amidination of bovine serum albumin using 2-imino-2-methoxyethyl 1-thioglycosides.
Preparation of some new neoglycoproteins by amidination of bovine serum albumin using 2-imino-2-methoxyethyl 1-thioglycosides.
复制标题
使用 2-亚氨基-2-甲氧基乙基 1-硫代糖苷通过牛血清白蛋白脒化制备一些新的新糖蛋白。
DOI：
10.1021/bi00562a030
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发表时间：
1980
期刊：
影响因子：
2.9
通讯作者：
Lee,YC
中科院分区：
文献类型：
--
作者：
Stowell,CP;Lee,YC
Christopher P. Stowell和Yuan Chuan Lee*摘要：以相应的假硫脲衍生物和氯乙腈制备了ß- d -半乳糖、6-0-甲基-/3- d -半乳糖、- l-阿拉伯糖、0-D- focus、ß-L- focus、/3- d -葡萄糖、0-D-木糖、ß-D-allose、ß- d -甘露糖、2-乙酰氨基-2-脱氧-/3- d -葡萄糖、2-乙酰氨基-2-脱氧-0-D-葡萄糖和3-6 - >-甲基-/3- d -葡萄糖的氰乙基1-巯基糖苷。在甲醇溶液中用甲氧基钠处理后，氰甲基1-巯基糖苷的糖基中的腈功能转化为甲基亚胺酯，从而得到2-亚胺-2-甲氧基乙基1-巯基糖苷[Lee， Y. C., Stowell， CP, & Krantz， M. J.^ íeoglycoproteins，碳水化合物通过化学手段共价附着的蛋白质，长期以来一直用于研究糖蛋白碳水化合物配基的生物学作用。已经开发的用于各种目的将碳水化合物附着在蛋白质上的方法已经进行了回顾（Stowell & Lee, 1980）。在温和条件下将碳水化合物附着在蛋白质上的有效方法之一是使用2-亚胺-2-甲氧基乙基1-硫代糖苷（IME-thioglycosides） 1 （Lee et al., 1976）。这些试剂在糖基中含有甲基亚胺酯功能，它与蛋白质的氨基反应形成脒。ime -巯基苷也被用来使酶酰胺化而不丧失活性（Lee et al., 1976; Stowell, 1978）。0- d -半乳糖吡喃糖、ß- d -葡萄糖吡喃糖、-d -甘露吡喃糖和2-乙酰氨基-2-脱氧-/3-葡萄糖吡喃糖通过这些试剂附着的几种蛋白质的新糖蛋白已被用来表征几种糖蛋白结合系统的特异性（Krantz等，1976;Stowell & Lee, 1978； Stahl等，1978）。我们现在报道了一些新的ime -巯基糖苷的制备，以及它们的稳定性、酰胺化条件和合成的氨基糖蛋白的稳定性的研究结果。
Christopher P. Stowell and Yuan Chuan Lee* abstract: The cyanomethyl 1-thioglycosides of ß-D-galactose, 6-0-methyl-/3-D-galactose,«-L-arabinose, 0-D-fucose, ß-L-fucose,/3-D-glucose, 0-D-xylose, ß-D-allose,«-D-mannose, 2-acetamido-2-deoxy-/3-D-glucose, 2-acetamido-2-deoxy-/3-D-galactose, 2-deoxy-0-D-glucose, and 3-6>-methyl-/3-D-glucose were prepared from the respective pseudothiourea derivatives and chloroacetonitrile. The nitrile function in the aglycon of the cyanomethyl 1-thioglycosides was converted to a methyl imido ester by treatment with sodium methoxide in methanolic solutions, thereby affording the 2-imino-2-methoxyethyl 1-thioglycosides [Lee, Y. C., Stowell, CP, & Krantz, M. J.^ íeoglycoproteins, proteins to which carbohydrates have been covalently attached by chemical means, have long been used tostudy the biological role of the carbohydrate prosthetic group of glycoproteins. The methods which have been developed for attachingcarbohydrates to proteins for various purposes have been reviewed (Stowell & Lee, 1980). One of the effective methods for attaching carbohydrates to proteins under mild conditions is to use the 2-imino-2-methoxyethyl 1-thioglycosides (IME-thioglycosides) 1 (Lee et al., 1976). These reagents contain a methyl imido ester function in the aglycon which reacts with the amino groups of proteins to form amidines. The IME-thioglycosides have also been used to amidinate enzymes with no loss of activity (Lee et al., 1976; Stowell, 1978). The neoglycoproteins of several proteins to which 0-D-galactopyranose, ß-D-glucopyranose,-D-mannopyranose, and 2-acetamido-2-deoxy-/3-glucopyranose had been attached by using these reagents have been used to characterize the specificity of several glycoprotein-binding systems (Krantz et al., 1976; Stowell & Lee, 1978; Stahl et al., 1978). We now report the preparation of a number of new IME-thioglycosides, as well as the results of an investigation of their stability, the conditions for amidination, and the stability of the resultant amidinoneoglycoproteins.
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影响因子：
3.1
作者：
Stefan Chipowsky;C. L. Yuan
通讯作者：
C. L. Yuan
硫代糖苷与蛋白质的结合：增强肝膜结合。
影响因子：
2.9
作者：
M. Krantz;N. Holtzman;C. Stowell;Yuan C. Lee;Jerry W. Weiner;Hans H. Liu
通讯作者：
Hans H. Liu
[6] 自动液相色谱法分析糖类
DOI：
--
发表时间：
1972
期刊：
影响因子：
--
作者：
Y. C. Lee
通讯作者：
Y. C. Lee
芳香腈中亚氨基酯的形成
DOI：
--
发表时间：
1956
期刊：
影响因子：
--
作者：
N. S. Bayliss;R. L. Heppolette;L. H. Little;Joseph A. Miller
通讯作者：
Joseph A. Miller
d-葡萄糖基新糖蛋白与肝脱唾液酸糖蛋白受体的结合。
影响因子：
4.8
作者：
C. Stowell;Y. Lee
通讯作者：
Y. Lee