Synthesis of heparin-like oligosaccharides

Posted on:2015-04-30

Degree:Ph.D

Type:Thesis

University:Purdue University

Candidate:Morales Collazo, Oscar

Full Text:PDF

GTID:2471390020951999

Subject:Chemistry

Abstract/Summary:

Heparan-like disaccharides (GlcN(alpha1→4)Glc) bearing a beta-ethylamino linker were prepared by solution-phase synthesis, using an orthogonal protecting group strategy to obtain a diverse set of polysulfated derivatives (sulfoforms) from a common intermediate. This approach generated sulfoforms bearing a 6-O-sulfate in the beta-Glc moiety and variable sulfation patterns in the alpha-GlcN unit, to support screening assays against heparin-binding proteins and Chlamydia trachomatis, a major bacterial pathogen in sexually trasmitted infections. A synthetic route toward an unsulfated heparan trisaccharide, GlcA(beta1→4)GlcNAc(alpha1→4)GlcAbeta, was also developed using a convergent approach, in order to confirm its high affinity for the signaling factor FGF-2, and to evaluate its potential role in promoting chlamydial infections.

Keywords/Search Tags:

Synthesis

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