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Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase

Title
Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase
Authors
Jeong L.S.Yoo S.J.Lee K.M.Koo M.J.Choi W.J.Kim H.O.Moon H.R.Lee M.Y.Park J.G.Lee S.K.Chun M.W.
Ewha Authors
이강만정낙신이상국
SCOPUS Author ID
이강만scopus
Issue Date
2003
Journal Title
Journal of Medicinal Chemistry
ISSN
0022-2623JCR Link
Citation
vol. 46, no. 2, pp. 201 - 203
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 °C). Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A. A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition.
DOI
10.1021/jm025557z
Appears in Collections:
약학대학 > 약학과 > Journal papers
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