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Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion

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Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion

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Title: Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion
Author: Ma, Jimei; Zhao, Yanying; Ng, Simon; Zhang, Jing; Zeng, Jing; Than, Aung; Chen, Peng; Liu, Xue-Wei
Copyright year: 2010
Abstract: Tamiflu is currently the most effective drug for the treatment of influenza, but the insufficient supply and side-effects of this drug demand urgent solutions. We present a practical synthesis of Tamiflu by using novel synthetic routes, cheap reagents, and the abundantly available starting material D-glucal. The strategy features a Claisen rearrangement of hexose to obtain the cyclohexene backbone and introduction of diamino groups through tandem intramolecular aziridination and ring opening. In addition, this synthetic protocol allows late-stage functionalization for the flexible synthesis of Tamiflu analogues. By using the synthesized Tamiflu and its active metabolite (oseltamivir carboxylate), we investigated their influences on neuroendocrine PC12 cells in various aspects. It was discovered that oseltamivir carboxylate significantly inhibits the vesicular exocytosis (regulated secretion) of PC12 cells, and suggests a mechanism underlying the Tamiflu side-effects, in particular its possible adverse influences on neurotransmitter release in the central nervous system.
Subject: DRNTU::Science::Biological sciences::Biochemistry.
Type: Journal Article
Series/ Journal Title: Chemistry - a European journal
School: School of Physical and Mathematical Sciences
Rights: © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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