Document Detail

Chemical Modifications of Alginates in Organic Solvent Systems.
MedLine Citation:
PMID:  22004188     Owner:  NLM     Status:  Publisher    
Alginates are (1→4) linked linear copolysaccharides composed of β-D-mannuronic acid (M) and its C-5 epimer, α-L-guluronic acid (G). Several strategies to synthesize organically modified alginate derivatives have been reported, but almost all chemistries are performed in either aqueous or aqueous-organic media. The ability to react alginates homogeneously in organic solvents would open up access to a wide range of new chemistries and derivatives. However, past attempts have been restricted by the absence of methods for alginate dissolution in organic media. We therefore report a strategy to dissolve tetrabutylammonium (TBA) salts of alginic acid in polar aprotic solvents containing tetrabutylammonium fluoride (TBAF). Acylation of TBA-alginate was performed under homogeneous conditions, such that both M and G residues were acetylated up to a total degree of substitution (DS) ≈ 1.0. Performing the same reaction under heterogeneous conditions resulted in selective acylation of M residues. Regioselectivity in the acylated alginate products was studied and degradation under basic reaction conditions was probed.
Siddhesh Nitin Pawar; Kevin J Edgar
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-10-17
Journal Detail:
Title:  Biomacromolecules     Volume:  -     ISSN:  1526-4602     ISO Abbreviation:  -     Publication Date:  2011 Oct 
Date Detail:
Created Date:  2011-10-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100892849     Medline TA:  Biomacromolecules     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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