Synthesis of C-glycopolymers as mimics of fungal beta-glucans

John August Bohn, Purdue University

Abstract

Several naturally occurring $\beta$-glucans have demonstrated immunomodulating activities. All clinically active polymers have a linear backbone of (1$\rightarrow$3)-linked $\beta$-D-glucopyranosyl units with single (1$\rightarrow$6)-linked glucopyranosyl units attached at every third to fifth backbone unit. Use of these polymers is limited by their low solubility in water. In order to test the importance of the side-chain sugar units and to make similar water-soluble polymers, polyacrylamides with C-($\beta$-D-glucopyranosyl) derivatives attached randomly to the backbone were prepared. These glycopolymers were constructed in two ways. Synthesis of a C-glucopyranosyl-acrylamide derivative and copolymerizing this derivative with acrylamide resulted in a lower incorporation of the monomer than was desired. In this method, a series of monomers was made in which the aglycon provided a range of spacer-arm lengths. A different strategy was then employed. It involved preparing a copolymer of acrylamide and methyl acrylate, and then attaching the C-glycosylmethylamine monomer to the copolymer at the position of the methyl ester groups in the polymer. In application of this method, only a $\beta$-alanyl unit was used as the spacer arm. Proton and $\sp{13}$C-nmr, GPC, viscosity, and chemical methods were used to characterize these latter polymers.

Degree

Ph.D.

Advisors

BeMiller, Purdue University.

Subject Area

Immunology|Pharmacology|Biomedical research

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