Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni
Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni
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DOI：
10.1016/j.carres.2012.08.008
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发表时间：
2012-11-01
影响因子：
3.1
通讯作者：
Hada, Noriyasu
中科院分区：
文献类型：
--
作者：
Kanaya, Takayuki;Schweizer, Frank;Hada, Noriyasu
从曼氏血吸虫中发现的三种中性鞘糖脂和六种寡糖衍生物的立体控制合成已经完成。一种五糖鞘糖脂β-D-Galp-（1 -> 4）-[α-L-Fucp-（1 -> 3）]-β-D-GlcpNAc-（1 -> 3）-β-D-GalpNAc-（1 -> 4）-β-D-Glcp-（11）-Cer（1），二种六糖鞘糖脂α-L-Fucp-（1 -> 3）-beta-D-Galp-（1 -> 4）-[α-L-Fucp-（1 -> 3）]-beta-D-GlcpNAc-（1 -> 3）-beta-D-GalpNAc-（1 -> 4）-beta-D-Glcp-（11）-Cer（2）和b-D-Galp-（1 -> 4）-[α-L-Fucp-（1 -> 3）]-β-D-GlcpNAc-（1-> 3）-β-D-GlcpNAc-（1 -> 4）-β-D-Glcp-（11）-Cer（3），连同它们的非还原性末端三糖和四糖，通过嵌段合成法合成β-D-Galp-（1 -> 4）-[α-L-Fucp-（1 -> 3）]-β-D-GlcpNAcOR（4）和α-L-Fucp-（1 -> 3）-β-D-Galp-（1 -> 4）-[α-L-Fucp-（1 -> 3）]-β-D-GlcpNAcOR（5）。此外，糖体鞘糖脂的非还原性末端寡糖，β-D-GalpNAc-（1 -> 4）-[α-L-Fucp-（1 -> 3）]-β-D-GlcpNAcOR（6），α-L-Fucp-（1 -> 3）-β-D-GalpNAc-（1 -> 4）-[α-L-Fucp-（1 -> 3）] -β-D-GlcpNAcOR（7），α-L-Fucp-（1 -> 3）-β-D-GalpNAc-（1 -> 4）-[α-L-Fucp-（1 -> 2）-α-L-Fucp-（1 -> 3）]-β-D-GlcpNAcOR（8）和α-L-Fucp-（1 -> 3）-β-D-GalpNAc-（1 -> 4）-[α-L-Fucp-（1 -> 2）-α-L-Fucp-（1-> 2）-α-L-Fucp-（1 -> 2）-α-L-Fucp-（1 -> 3）]-β-D-GlcpNAcOR（9）[R = 2-（三甲基硅基）乙基]作为探针，探讨其对血吸虫病患者血清的诊断潜力。(C)2012爱思唯尔有限公司保留所有权利。
Stereocontrolled syntheses of three neutral glycosphingolipids and six oligosaccharide derivatives found from the parasite Schistosoma mansoni have been accomplished. A pentasaccharide glycosphingolipid beta-D-Galp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAc-(1 -> 3)-beta-D-GalpNAc-(1 -> 4)-beta-D-Glcp-(1 1)-Cer (1), two hexasaccharide glycosphingolipids alpha-L-Fucp-(1 -> 3)-beta-D-Galp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAc-(1 -> 3)-beta-D-GalpNAc-(1 -> 4)-beta-D-Glcp-(1 1)-Cer (2) and b-D-Galp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAc-( 1 -> 3)-beta-D-GlcpNAc-(1 -> 3)-beta-D-GalpNAc-(1 -> 4)-beta-D-Glcp-(1 1)-Cer (3), together with their non-reducing end tri- and tetrasaccharides, beta-D-Galp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAcOR (4) and alpha-L-Fucp-(1 -> 3)-beta-D-Galp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAcOR (5), were synthesized by block synthesis. Moreover, non-reducing end oligosaccharides of schistosomal glycosphingolipids, beta-D-GalpNAc-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAcOR (6), alpha-L-Fucp-(1 -> 3)-beta-D-GalpNAc-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)] -beta-D-GlcpNAcOR (7), alpha-L-Fucp-(1 -> 3)-beta-D-GalpNAc-(1 -> 4)-[alpha-L-Fucp-(1 -> 2)-alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAcOR (8) and alpha-L-Fucp-(1 -> 3)-beta-D-GalpNAc-(1 -> 4)-[alpha-L-Fucp-(1 -> 2)-alpha-L-Fucp-(1 -> 2)-alpha-L-Fucp-(1 -> 3)]-beta-D-GlcpNAcOR (9) [R = 2-(trimethylsilyl) ethyl], were synthesized as probes to explore their diagnostic potential to detect schistosomiasis from patients' sera. (C) 2012 Elsevier Ltd. All rights reserved.