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Decoration of chondroitin polysaccharide with threonine : synthesis, conformational study, and ice-recrystallization inhibition activity
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Laezza, Antonio, Casillo, Angela, Cosconati, Sandro, Biggs, Caroline I., Fabozzi, Antonio, Paduano, Luigi, Iadonisi, Alfonso, Novellino, Ettore, Gibson, Matthew I., Randazzo, Antonio, Corsaro, Maria M. and Bedini, Emiliano (2017) Decoration of chondroitin polysaccharide with threonine : synthesis, conformational study, and ice-recrystallization inhibition activity. Biomacromolecules . doi:10.1021/acs.biomac.7b00326 ISSN 1526-4602.
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Official URL: http://doi.org/10.1021/acs.biomac.7b00326
Abstract
Several threonine (Thr)- and alanine (Ala)-rich antifreeze glycoproteins (AFGPs) and polysaccharides act in nature as ice recrystallization inhibitors. Among them, the Thr-decorated capsular polysaccharide (CPS) from the cold-adapted Colwellia psychrerythraea 34H bacterium was recently investigated for its cryoprotectant activity. A semisynthetic mimic thereof was here prepared from microbial sourced chondroitin through a four-step strategy, involving a partial protection of the chondroitin polysaccharide as a key step for gaining an unprecedented quantitative amidation of its glucuronic acid units. In-depth NMR and computational analysis suggested a fairly linear conformation for the semisynthetic polysaccharide, for which the antifreeze activity by a quantitative ice recrystallization inhibition assay was measured. We compared the structure–activity relationships for the Thr-derivatized chondroitin and the natural Thr-decorated CPS from C. psychrerythraea.
Item Type: | Journal Article | ||||||
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Subjects: | Q Science > QD Chemistry | ||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||
SWORD Depositor: | Library Publications Router | ||||||
Library of Congress Subject Headings (LCSH): | Polysaccharides -- Synthesis, Antifreeze proteins, Alanine | ||||||
Journal or Publication Title: | Biomacromolecules | ||||||
Publisher: | American Chemical Society (ACS) | ||||||
ISSN: | 1526-4602 | ||||||
Official Date: | 11 July 2017 | ||||||
Dates: |
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DOI: | 10.1021/acs.biomac.7b00326 | ||||||
Status: | Peer Reviewed | ||||||
Publication Status: | Published | ||||||
Reuse Statement (publisher, data, author rights): | ** From Crossref via Jisc Publications Router. | ||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||
Date of first compliant deposit: | 18 July 2017 | ||||||
Date of first compliant Open Access: | 26 June 2018 | ||||||
Funder: | European Research Council (ERC) | ||||||
Grant number: | Starter Grant CRYOMAT 638661 |
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