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

Jimei Ma¹, Yanying Zhao², Simon Ng¹, Jing Zhang², Jing Zeng¹, Aung Than², Peng Chen² & Xuewei Liu¹

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1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371
2. Division of Bioengineering, School of Chemical and Biomedical Engineering, Nanyang Technological University, Singapore 637457

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Date:

Received 19 June 2009 16:47 UTC; Posted 22 June 2009

Subjects:

Chemistry, Molecular Cell Biology

Tags:

• Chemical synthesis
• Cell Biology
• Cell Secretion

Abstract:

Tamiflu is currently the most effective drug for the treatment of influenza. But the unmet supply and side effects of this drug demand urgent solutions. In this article, a practical synthesis of Tamiflu was developed using novel synthetic routes, cheap reagents, and abundantly available starting material D-glucose. In addition, our synthetic scheme allows late-stage functionalization for readily and flexible synthesis of Tamiflu analogues. 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 inhibited the vesicular exocytosis (regulated secretion) of PC12 cells, postulating a mechanism underlying the Tamiflu side-effects, particularly, its possible adverse influences on neurotransmitter release in the central nervous system.

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This document is licensed to the public under the Creative Commons Attribution 3.0 License

How to cite this document:

Ma, Jimei, Zhao, Yanying, Ng, Simon, Zhang, Jing, Zeng, Jing, Than, Aung, Chen, Peng, and Liu, Xuewei. Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion. Available from Nature Precedings <http://hdl.handle.net/10101/npre.2009.3351.1> (2009)

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