Controlled synthesis of O-glycopolypeptide polymers and their molecular recognition by lectins

TitleControlled synthesis of O-glycopolypeptide polymers and their molecular recognition by lectins
Publication TypeJournal Article
Year of Publication2012
AuthorsPati, D, Shaikh, AY, Das, S, Nareddy, PKumar, Swamy, MJ, Hotha, S, Gupta, SSen
JournalBiomacromolecules
Volume13
Issue5
Pagination1287-1295
Date PublishedMAY
Type of ArticleArticle
ISSN1525-7797
Abstract

The facile synthesis of high molecular weight water-soluble O-glycopolypeptide polymers by the ring-opening polymerization of their corresponding N-carboxyanhydride (NCA) in very high yield (overall yield > 70%) is reported. The per-acetylated-O-glycosylated lysine-NCA monomers, synthesized using stable glycosyl donors and a commercially available protected amino acid in very high yield, was polymerized using commercially available amine initiators. The synthesized water-soluble glycopolypeptides were found to be alpha-helical in aqueous solution. However, we were able to control the secondary conformation of the glycopolypeptides (alpha-helix vs nonhelical structures) by polymerizing raceznic amino acid glyco NCAs. We have also investigated the binding of the glycopolypeptide poly(alpha-manno-O-lys) with the lectin Con-A using precipitation and hemagglutination assays as well as by isothermal titration calorimetry (ITC). The ITC results clearly show that the binding process is enthalpy driven for both alpha-helical and nonhelical structures, with negative entropic contribution. Binding stoichiometry for the glycopolypeptide poly(alpha-manno-O-lys) having a nonhelical structure was slightly higher as compared to the corresponding polypeptide which adopted an alpha-helical structure.

DOI10.1021/bm201813s
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)5.371
Divison category: 
Chemical Engineering & Process Development