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Carbohydrate‐Protein Interactions with Poly‐amido‐saccharides (PASs) as Unique Carbohydrate‐Inspired Polymer Structures
Author(s) -
Chin Stacy L.,
Grinstaff Mark W.
Publication year - 2016
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.30.1_supplement.1097.2
Subject(s) - chemistry , pyranose , polysaccharide , biochemistry , carbohydrate , glycobiology , glycopolymer , polymer , stereochemistry , polymerization , glycan , glycoprotein , organic chemistry
Natural polysaccharides are of significant interest in biochemistry research because of their structural diversity and essential roles in metabolism, energy storage, cellular signaling, protein recognition, and other physiological processes. However the synthesis of polysaccharides is challenging due to the presence of many similar functional groups and the large number of stereocenters throughout the polymer structure. In response to the need for reliable approaches to prepare polysaccharides, we reported a synthetic method to prepare well‐defined, enantiopure carbohydrate polymers, termed poly‐amido‐saccharides (PASs), using a controlled anionic polymerization of b‐lactam sugar monomers. Unlike natural polysaccharides, in which sugar units are joined by ether linkages, pyranose units in PASs are linked through the 1‐and 2‐positions by an amide group, which affords PASs with unique structural features and interesting chemical properties. We recently found that PASs 1) possess a helical conformation in their secondary structure, 2) are able to maintain its rigid structure under varying pH, temperature, ionic strength, and denaturing conditions, and 3) are non‐cytotoxic and can be endocytosed across different mammalian cell lines. Our initial investigation indicate that glucose‐derived PAS (glc‐PAS) structures can be recognized by lectin concanavalin A at the same site as glucose through binding activity assays, which suggests the potential for PASs to serve as natural polysaccharide mimics. Based on this preliminary result, we hypothesize that sulfated galactose‐derived PAS (gal‐PAS) structures can potentially interact proteins in the coagulation cascade and posses anticoagulant‐like properties, similarly to heparin. The synthesis and characterization of glc‐PAS, gal‐PAS, and sulfated glc‐PAS polymer structures with via IR, NMR, and GPC will also be discussed.