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Synthesis and anti‐HIV activity of 6‐amino‐6‐deoxy‐(1→3)‐β‐ D ‐curdlan sulfate
Author(s) -
Borjihan Gereltu,
Zhong Guiyun,
Baigude Huricha,
Nakashima Hedeki,
Uryu Toshiyuki
Publication year - 2003
Publication title -
polymers for advanced technologies
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.61
H-Index - 90
eISSN - 1099-1581
pISSN - 1042-7147
DOI - 10.1002/pat.315
Subject(s) - curdlan , sulfation , chemistry , pyridine , sodium borohydride , dimethylformamide , dimethyl sulfoxide , sodium azide , organic chemistry , stereochemistry , medicinal chemistry , biochemistry , solvent , polysaccharide , catalysis
6‐Amino‐6‐deoxy‐(1→3)‐β‐ D ‐curdlan sulfate was synthesized in three steps. First, curdlan was azidized by lithium azide (LiN 3 ) and carbon tetrabromide (CBr 4 ) with triphenylphosphine (Ph 3 P) in dimethylformamide (DMF). Second, the azido group was reduced to an amino group with sodium borohydride (NaBH 4 ) in dimethyl sulfoxide (DMSO) to afford 6‐amino‐6‐deoxy‐(1→3)‐β‐ D ‐curdlan. Third, sulfation of the amino‐group‐containing curdlan with a sulfur trioxide‐pyridine complex produced a 6‐amino‐6‐deoxy‐(1→3)‐β‐ D ‐curdlan sufate exhibiting high anti‐HIV (human immunodeficiency virus) activity (EC 50 = 0.912 µg/ml) and low cytotoxicity (CC 50 = 2512 µg/ml). Copyright © 2003 John Wiley & Sons, Ltd.
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