Synthesis of a monophosphoryl derivative of Escherichia coli lipid A and its efficient coupling to a tumor-associated carbohydrate antigen.
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.
Tang
Shouchu
S
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.
Wang
Qianli
Q
Guo
Zhongwu
Z
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000480:Alkynes / Q000737:chemistry; D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry* / Q000276:immunology; D002241:Carbohydrates / Q000737:chemistry; D004926:Escherichia coli / Q000737:chemistry; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000276:Adjuvants, Immunologic; D000480:Alkynes; D015295:Antigens, Tumor-Associated, Carbohydrate; D002241:Carbohydrates; D008050:Lipid A; C048436:monophosphoryl lipid A