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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Adjuvants, Immunologic / chemical synthesis*
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Adjuvants, Immunologic / chemistry
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Adjuvants, Immunologic / pharmacology
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Alkynes / chemistry
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Antigens, Tumor-Associated, Carbohydrate / chemistry*
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Antigens, Tumor-Associated, Carbohydrate / immunology
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Carbohydrates / chemistry
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Escherichia coli / chemistry
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Lipid A / analogs & derivatives*
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Lipid A / chemical synthesis
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Lipid A / chemistry
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Lipid A / pharmacology
Substances
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Adjuvants, Immunologic
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Alkynes
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Antigens, Tumor-Associated, Carbohydrate
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Carbohydrates
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Lipid A
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monophosphoryl lipid A