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- Title
Regioselective synthesis of 6-amino- and 6-amido-6-deoxypullulans.
- Authors
Pereira, Junia; Edgar, Kevin
- Abstract
Hydrophobically modified polysaccharides that contain amine and amide groups possess valuable features for drug delivery and other applications. These chemical groups are known to play a fundamental role in the biological activity of important polysaccharides. Pullulan is known for its non-toxicity and biocompatibility, therefore, we have applied the versatile Staudinger reaction for the synthesis of regioselectively substituted pullulan derivatives containing amine or amide groups with promise for biomedical applications. The synthesis began with the regioselective bromination of pullulan at C-6 with N-bromosuccinimide and triphenylphosphine, providing 6-bromo-6-deoxy-pullulan, which is soluble in a range of organic solvents and therefore is a dynamic intermediate for the synthesis of other pullulan derivatives. Azide displacement of bromide from 6-bromo-6-deoxy-pullulan esters yielded the corresponding 6-azido-6-deoxy-pullulan esters. Staudinger reduction of these azides efficiently and chemoselectively afforded the corresponding amino- or amidopullulans.
- Subjects
POLYSACCHARIDE synthesis; REGIOSELECTIVITY (Chemistry); DRUG delivery devices; BIOCOMPATIBILITY; BROMINATION
- Publication
Cellulose, 2014, Vol 21, Issue 4, p2379
- ISSN
0969-0239
- Publication type
Article
- DOI
10.1007/s10570-014-0259-6