在多聚乙二醇上通过化学酶法支持合成3 - 硫酸化路易斯a五糖。

Chemo-enzymatic supported synthesis of the 3-sulfated Lewis a pentasaccharide on a multimeric polyethylene glycol.

作者信息

Malleron Annie, Le Narvor Christine

机构信息

Laboratoire de Chimie Organique Multifonctionnelle, Equipe Glycochimie Moléculaire et Macromoléculaire, Centre National de la Rercherche Scientifique, UMR 8182, Bâtiment 420, Universite Paris-Sud, Orsay, France.

出版信息

Carbohydr Res. 2008 Apr 7;343(5):970-6. doi: 10.1016/j.carres.2008.01.005. Epub 2008 Jan 15.

DOI:10.1016/j.carres.2008.01.005

PMID:18280461

Abstract

The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage.

摘要

在基于多聚体的聚乙二醇载体上合成了3-硫酸化路易斯（a）五糖。将O-(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基)-(1→3)-4,6-二-O-乙酰基-2-脱氧-2-邻苯二甲酰亚氨基-β-D-吡喃葡萄糖基三氯乙酰亚胺与连接在聚合物上的(2,6-二-O-乙酰基-β-D-吡喃半乳糖基)-(1→4)-(2,3,6-三-O-乙酰基-β-D-葡萄糖苷)偶联，得到乳糖-N-四糖，然后使用亚锡法在末端半乳糖的3-OH位置进行区域选择性硫酸化。使用固定化岩藻糖基转移酶FucTIII对硫酸化四糖进行岩藻糖基化，裂解后得到标题化合物。