期刊
BIOMACROMOLECULES
卷 13, 期 4, 页码 992-1001出版社
AMER CHEMICAL SOC
DOI: 10.1021/bm2017004
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资金
- Institute for Critical Technologies and Applied Science (ICTAS) for an ICTAS
- Macromolecules and Interfaces Institute (MII)
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1126534] Funding Source: National Science Foundation
Aminated polysaccharides have been extensively investigated for a wide range of biomedical applications. To achieve targeted properties such as solubility and miscibility, it can be beneficial to modify the polysaccharide hydroxyl groups; selectively while leaving the amino groups unmodified. This tends to be difficult because of the higher reactivity of primary amines than hydroxyl groups toward electrophilic reagents. We describe herein a new method that can produce O-acylated, aminated polysaccharides with extremely high selectivity. In this procedure, 6-azido-6-deoxy-cellulose esters are synthesized from 6-bromo-6-deoxy-cellulose esters. The azide groups are then selectively and mildly reduced using the Staudinger reaction to produce 6-amino-6-deoxy-2,3-di-O-acyl-cellulose derivatives. This demonstrates the effectiveness of the Staudinger reduction on a polysaccharide substrate in the presence of easily reducible ester groups.
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