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Synthesis of a Monophosphoryl Derivative of Escherichia coli Lipid A and Its Efficient Coupling to a Tumor-Associated Carbohydrate Antigen

✍ Scribed by Shouchu Tang; Qianli Wang; Zhongwu Guo

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 296 KB
Volume: 16
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200902153

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✦ Synopsis

Abstract

Monophosphoryl lipid A is a safe and potent immunostimulant and vaccine adjuvant, which is potentially useful for the development of effective carbohydrate‐based conjugate vaccines. This paper presents a convergent and efficient synthesis of a monophosphoryl derivative of E. coli lipid A that has an alkyne functionality at the reducing end, which is suitable for coupling with various molecules. The coupling of this derivative to an N‐modified analogue of tumor‐associated antigen GM3 through click chemistry is also presented.

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