Glycosyl Imidates, 52. Synthesis of Globotriaosylceramide (Gb3) and Isoglobotriaosylceramide (isoGb3)
Glycosyl Imidates, 52. Synthesis of Globotriaosylceramide (Gb3) and Isoglobotriaosylceramide (isoGb3)
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糖基亚氨酸酯，52。三酰神经酰胺球蛋白 (Gb3) 和三酰神经酰胺异球蛋白酯 (isoGb3) 的合成
DOI：
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发表时间：
1992
期刊：
影响因子：
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通讯作者：
R. Schmidt
中科院分区：
文献类型：
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作者：
D. Qiu;R. Schmidt
以o -半乳糖-三氯乙酸酯5α为供体，4b- o -无保护的乳糖7为受体，合成了globotriaosyl神经酰胺(1)；7很容易从乳糖中获得。通过“反向过程”进行糖基化，优先得到α-三糖8α。它转化为o -乙酰基保护的三氯乙酸酯11α，为3- o -苯甲酰-叠氮膦氨酸12的β选择性糖基化提供了有效的三酰基供体。得到的溶糖鞘脂衍生物13直接转化为n -棕榈酰衍生物14，对靶分子1进行o -去酰化。对于异血红蛋白三烷基神经酰胺(2)的合成基本上采用了相同的程序。因此，通过从5α和3b， 4b- o无保护的乳糖受体15开始，使用糖苷键形成的倒置程序优先得到三糖16α，将其转化为三烷基供体24α。应用叠氮膦糖基化程序得到溶鞘脂25和随后的鞘脂糖26；脱保护后得到目标分子2。
The synthesis of globotriaosylceramide (1) was based on O-galactosyl trichloroacetimidate 5α as donor and 4b-O-unprotected lactose 7 as acceptor; 7 was readily accessible from lactose. Glycosylation by an “inverted procedure” afforded preferentially the α-trisaccharide 8α. Its transformation into the O-acetyl-protected trichloroacetimidate 11α led to an efficient triaosyl donor for the β-selective glycosylation of 3-O-benzoyl-azidosphingosine 12. The obtained lysoglycosphingolipid derivative 13 was directly converted into the N-palmitoyl derivative 14 which gave upon O-deacylation the target molecule 1. For the synthesis of isoglobotriaosylceramide (2) essentially the same procedure was applied. Thus, by starting from 5α and 3b, 4b-O-unprotected lactose acceptor 15 the use of the inverted procedure for glycoside-bond formation gave preferentially trisaccharide 16α, which was transformed into triaosyl donor 24α. Application of the azidosphingosine glycosylation procedure afforded lysosphingolipid 25 and subsequently glycosphingolipid 26; after deprotection the target molecule 2 was obtained.
人类畸胎瘤中的新球系列鞘糖脂可与针对发育调节抗原（阶段特异性胚胎抗原 3）的单克隆抗体发生反应。
DOI：
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发表时间：
1983
期刊：
The Journal of biological chemistry
影响因子：
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作者：
Kannagi,R;Levery,SB;Ishigami,F;Hakomori,S;Shevinsky,LH;Knowles,BB;Solter,D
通讯作者：
Solter,D
伯基特淋巴瘤和类淋巴母细胞系中伯基特淋巴瘤相关抗原（三酰神经酰胺）表达的酶学和组织差异。
DOI：
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发表时间：
1984
期刊：
The Journal of biological chemistry
影响因子：
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作者：
Wiels,J;Holmes,EH;Cochran,N;Tursz,T;Hakomori,S
通讯作者：
Hakomori,S
从人胚胎癌细胞中分离出的鞘糖脂的结构。
DOI：
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发表时间：
1986
期刊：
The Journal of biological chemistry
影响因子：
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作者：
Fukuda,MN;Bothner,B;Lloyd,KO;Rettig,WJ;Tiller,PR;Dell,A
通讯作者：
Dell,A