Synthesis and chain length-anti-HIV activity relationship of fully N- and O-sulfated homooligomers of tyrosine.
Fully N- and O-sulfated homooligomers from octamer to nonadecamer of tyrosine were obtained as their sodium salts, aO3S-[Tyr(SO3Na)]n-ONa (n = 8-19), from reaction mixtures of tyrosine with sulfur trioxide trimethylamine and pyridine comlexes, respectively, in pyridine. Their anti-HIV activity increased along with the increase of the chain length up to the dodecamer, maintained the same level to the length of the heptadecamer and then decreased. The maximal activity level was the same as or higher than that of dextran and curdlan sulfates.
Ueki
M
M
Department of Applied Chemistry, Science University of Tokyo, Japan. maueki@ch.kagu.sut.ac.jp
Watanabe
S
S
Saitoh
T
T
Nakashima
H
H
Yamamoto
N
N
Ogawara
H
H
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002461:Cell Line, Transformed / Q000187:drug effects / Q000382:microbiology; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D003588:Cytopathogenic Effect, Viral; D006801:Humans; D020128:Inhibitory Concentration 50; D009842:Oligopeptides; D013329:Structure-Activity Relationship; D014443:Tyrosine / Q000031:analogs & derivatives
D019380:Anti-HIV Agents; D009842:Oligopeptides; C005662:tyrosine O-sulfate; D014443:Tyrosine