19F型肺炎链球菌荚膜多糖三糖成分的合成
Synthesis of a trisaccharide component of the capsular polysaccharide of Streptococcus pneumoniae type 19F.
作者信息
Sugawara T, Igarashi K
机构信息
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
出版信息
Carbohydr Res. 1988 Feb 1;172(2):195-207. doi: 10.1016/s0008-6215(00)90854-1.
2-O-[4-O-(2-Acetamido-2-deoxy-beta-D-mannopyranosyl)-alpha-D- glucopyranosyl]-alpha,beta-L-rhamnopyranose, a structural component of the capsular polysaccharide of Streptococcus pneumoniae type 19F, has been synthesized by sequential glycosylation reactions using the glycosyl acceptor 2,2,2-trichloroethyl 3,4-di-O-benzyl-alpha-L-rhamnopyranoside (prepared from the known 2-O-acetyl-3,4-di-O-benzyl-alpha-L-rhamnopyranosyl chloride), and the glycosyl donors 4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl chloride and 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-alpha-D-mannopyranosyl bromide (prepared in seven steps from the known methyl 2-azido-4,6-O-benzylidene-2-deoxy-alpha-D-altropyranoside). The corresponding 8-(methoxycarbonyl)octyl glycoside has also been synthesized, by coupling of 8-(methoxycarbonyl)octyl trifluoromethanesulfonate and the sodium salt of 2-O-[4-O-(2-acetamido-4,6-di-O-acetyl-3-O-benzyl-2-deoxy-beta-D- mannopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl]-3,4-di-O- benzyl-alpha,beta-L-rhamnopyranose.
2-O-[4-O-(2-乙酰氨基-2-脱氧-β-D-甘露吡喃糖基)-α-D-吡喃葡萄糖基]-α,β-L-鼠李吡喃糖是肺炎链球菌19F型荚膜多糖的一种结构成分，它是通过糖基化反应顺序合成的，使用糖基受体2,2,2-三氯乙基3,4-二-O-苄基-α-L-鼠李吡喃糖苷（由已知的2-O-乙酰基-3,4-二-O-苄基-α-L-鼠李吡喃糖基氯制备）以及糖基供体4-O-乙酰基-2,3,6-三-O-苄基-α-D-吡喃葡萄糖基氯和4,6-二-O-乙酰基-2-叠氮基-3-O-苄基-2-脱氧-α-D-甘露吡喃糖基溴（由已知的甲基2-叠氮基-4,6-O-亚苄基-2-脱氧-α-D-阿卓吡喃糖苷经七步制备）。相应的8-(甲氧基羰基)辛基糖苷也已通过8-(甲氧基羰基)辛基三氟甲磺酸酯与2-O-[4-O-(2-乙酰氨基-4,6-二-O-乙酰基-3-O-苄基-2-脱氧-β-D-甘露吡喃糖基)-2,3,6-三-O-苄基-α-D-吡喃葡萄糖基]-3,4-二-O-苄基-α,β-L-鼠李吡喃糖的钠盐偶联而合成。
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