Synthesis of heparin-like oligosaccharides
Abstract
Heparan-like disaccharides (GlcN(α1→4)Glc) bearing a β-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 β-Glc moiety and variable sulfation patterns in the α-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(β1→4)GlcNAc(α1→4)GlcAβ, 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.
Degree
Ph.D.
Advisors
Wei, Purdue University.
Subject Area
Biochemistry|Organic chemistry
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