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American Chemical Society, Journal of the American Chemical Society, 39(129), p. 11892-11893, 2007

DOI: 10.1021/ja073992i

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Synthesis of Tamiflu and its Phosphonate Congeners Possessing Potent Anti-Influenza Activity

Journal article published in 2007 by Jim-Min Fang, Shi-Yun Wang, Keng-Chang Tsai, Yih-Shyun E. Cheng, An-Suei Yang, Ching-Yao Su, Shih-Chia Hsiao, Chi-Huey Wong, Jiun-Jie; Fang Jim-Min; Wang Shi-Yun; Tsai Keng-Chang; Cheng Yih-Shyun E.; Yang An-Suei; Hsiao Shih-Chia; Su Ching-Yao; Wong Chi-Huey Shie ORCID
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This paper is available in a repository.

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Abstract

Using d-xylose as an appropriate chiral precursor, we have synthesized active neuraminidase inhibitor oseltamivir, antiflu drug Tamiflu, and novel phosphonate congeners that exhibit even stronger antiflu activities by inhibiting the neuraminidases of the wild-type and H274Y mutant of H1N1 and H5N1 viruses. Molecular modeling of the neuraminidase−phosphonate complex indicates a pertinent binding mode of the phosphonate with three arginine residues in the active site. Discovery of such potent neuraminidase inhibitors will offer an opportunity to the development of new anti-influenza drugs.