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Synthesis of a monophosphoryl derivative of Escherichia coli lipid A and its efficient coupling to a tumor-associated carbohydrate antigen.

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.

SUBMITTER: Tang S

PROVIDER: S-EPMC2867242 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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Synthesis of a monophosphoryl derivative of Escherichia coli lipid A and its efficient coupling to a tumor-associated carbohydrate antigen.

Tang Shouchu S Wang Qianli Q Guo Zhongwu Z

Chemistry (Weinheim an der Bergstrasse, Germany) 20100101 4

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 clic ...[more]

PMID: 19943286

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Synthesis of a monophosphoryl lipid A derivative and its conjugation to a modified form of a tumor-associated carbohydrate antigen GM3.

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