Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf-(1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi

被引：28

作者：

Gallo-Rodriguez, C ^{[1
]}

Gil-Libarona, MA ^{[1
]}

Mendoza, VM ^{[1
]}

de Lederkremer, RM ^{[1
]}

机构：

[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, CIHIDECAR, RA-1428 Buenos Aires, DF, Argentina

来源：

TETRAHEDRON | 2002年 / 58卷 / 46期

关键词：

galactofuranose; mucins; Trypanosoma cruzi; D-galactono-1,4-lactone; glycosylation; trichloroacetimidate;

D O I：

10.1016/S0040-4020(02)01226-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of free beta-D-Galp-(1-->3)-beta-D-Galp-(1-->6)-[beta-D-Galf-(1-->4)]-D-G]cNAc and the corresponding alditol which has been previously isolated by reductive beta-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of beta-D-Galf-(1-->4)-D-GlcNAc with a donor derivative of beta-D-Galp-(1-->3)-D-Galp. The trichloroacetimidate method, as well as SnCl4-promoted condensation were utilized for the introduction of the galactofuranosyl unit. On the other hand, the glycosyl-aldonolactone approach, followed by reduction of the lactone with diisoamylborane, and further isomerization to the galactopyranose configuration gave the donor derivative, which was condensed by the trichloroacetimidate method. Moreover, a synthon for the introduction of the beta-D-Galp-(1-->3)-D-Galf unit is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9373 / 9380

页数：8

共 22 条

[1] The mucin-like glycoprotein super-family of Trypanosoma cruzi:: structure and biological roles [J].