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Title: Carbohydrate-derived molecular diversity : synthesis and application in cell biology
Authors: Ma, Jimei
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Issue Date: 2010
Source: Ma, J. M. (2010). Carbohydrate-derived molecular diversity : synthesis and application in cell biology. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: Tamiflu is currently the most effective drug for the treatment of influenza. In this part, a practical synthesis of Tamiflu was developed using novel synthetic route, cheap reagents, and abundantly available starting material D-glucal. This strategy features Claisen rearrangement of hexose to obtain the cyclohexene backbone and introduction of diamino groups through tandem intramolecular aziridination and ring opening. In addition, our synthetic protocol allows late-stage functionalization for facile and flexible synthesis of Tamiflu analogues. Using the synthesized Tamiflu and its active metabolite (oseltamivir carboxylate), we investigated their influence on morphology, proliferation, differentiation and vesicular exocytosis (regulated secretion) of neuroendocrine PC12 cells. It was found that oseltamivir carboxylate significantly inhibited the vesicular exocytosis of PC12 cells, postulating a mechanism underlying the Tamiflu side-effects, particularly, its possible adverse influences on neurotransmitter release in the central nervous system.
DOI: 10.32657/10356/42235
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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