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Synthesis of a Monophosphoryl Derivative of Escherichia coli Lipid A and Its Efficient Coupling to a Tumor‐Associated Carbohydrate Antigen
Author(s) -
Tang Shouchu,
Wang Qianli,
Guo Zhongwu
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902153
Subject(s) - lipid a , immunostimulant , conjugate , derivative (finance) , adjuvant , chemistry , escherichia coli , carbohydrate , glycosylation , combinatorial chemistry , antigen , biochemistry , biology , immunology , lipopolysaccharide , immune system , mathematical analysis , mathematics , gene , economics , financial economics
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.