合成一种含有鹦鹉热衣原体特异性分支 Kdo 三糖表位的糖缀合物。

Synthesis of a neoglycoconjugate containing a Chlamydophila psittaci-specific branched Kdo trisaccharide epitope.

机构信息

Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.

出版信息

Carbohydr Res. 2010 Mar 30;345(5):704-8. doi: 10.1016/j.carres.2009.12.015. Epub 2009 Dec 21.

DOI:10.1016/j.carres.2009.12.015

PMID:20116048

Abstract

The branched Kdo trisaccharide sodium (3-deoxy-alpha-D-manno-oct-2-ulopyranosyl)onate-(2-->8)-[sodium (3-deoxy-alpha-D-manno-oct-2-ulopyranosyl)onate-(2-->4)]-sodium (allyl 3-deoxy-alpha-D-manno-oct-2-ulopyranosid)onate has been prepared utilizing the regioselective glycosylation of the C-7, C-8 diol entity of a Kdo monosaccharide acceptor with a Kdo bromide donor followed by the attachment of the third Kdo unit to O-4 of the disaccharide intermediate. Deacetylation and hydrolysis of the methyl ester groups furnished the trisaccharide allyl glycoside which was converted into the corresponding 3-(2-aminoethylthio)propyl glycoside. Subsequent covalent attachment to bovine serum albumin furnished a neoglycoconjugate serving as an antigen for the induction of Chlamydophila psittaci-specific monoclonal antibodies.

摘要

分支 Kdo 三糖钠盐（3-脱氧-α-D-甘露辛吡喃糖基）-（2→8）-[（3-脱氧-α-D-甘露辛吡喃糖基）-（2→4）]-（烯丙基 3-脱氧-α-D-甘露辛吡喃糖苷基）-（3-脱氧-α-D-甘露辛吡喃糖酸钠）已通过 Kdo 溴化物供体与 Kdo 单糖受体的 C-7、C-8 二醇基的区域选择性糖基化制备，然后将第三个 Kdo 单元连接到二糖中间体的 O-4 上。脱乙酰化和甲酯基团的水解提供了三糖烯丙基糖苷，将其转化为相应的 3-（2-氨基乙基硫代）丙基糖苷。随后与牛血清白蛋白的共价连接提供了一种作为诱导鹦鹉热衣原体特异性单克隆抗体的抗原的新糖缀合物。