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

Chemistry : a European Journal
Shouchu TangZhongwu Guo

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.

References

Feb 1, 1994·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·E T RietschelF Di Padova
Aug 17, 1993·Carbohydrate Research·H Rembold, R R Schmidt
Mar 6, 1999·Current Opinion in Microbiology·R P Darveau
May 26, 1999·Infectious Disease Clinics of North America·D C MorrisonA Shnyra
Oct 20, 1999·Methods : a Companion to Methods in Enzymology·J R Baldridge, R T Crane
Dec 2, 1999·Journal of Medicinal Chemistry·D A JohnsonV G Brookshire
Mar 15, 2001·Proceedings of the National Academy of Sciences of the United States of America·V KudryashovK O Lloyd
Jul 11, 2002·Microbes and Infection·Marina A Dobrovolskaia, Stefanie N Vogel
Sep 25, 2002·Microbes and Infection·Clett ErridgeIan R Poxton
Oct 16, 2002·Trends in Microbiology·David H PersingSteven G Reed
Feb 27, 2003·Journal of the American Chemical Society·Ning YinPaul B Savage
Jun 6, 2003·Journal of the American Chemical Society·Alexei V DemchenkoGeert-Jan Boons
Jul 15, 2003·Clinical Microbiology Reviews·Edwin S Van AmersfoortJohan Kuiper
Sep 10, 2004·Organic Letters·Balaji Santhanam, Geert-Jan Boons
Sep 17, 2004·Chemistry : a European Journal·Balaji SanthanamGeert-Jan Boons
Feb 4, 2005·Journal of Medicinal Chemistry·Yanbin PanZhongwu Guo
Mar 30, 2007·Journal of the American Chemical Society·Yanghui ZhangGeert-Jan Boons
May 22, 2007·Bioorganic & Medicinal Chemistry·Yanghui ZhangGeert-Jan Boons
Aug 1, 2008·Cellular and Molecular Life Sciences : CMLS·C R Casella, T C Mitchell
Jan 16, 2009·Chembiochem : a European Journal of Chemical Biology·Sampat IngaleGeert-Jan Boons
Apr 17, 2001·Angewandte Chemie·Hiroaki YoshizakiShoichi Kusumoto

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Citations

Jan 23, 2016·Chemical Reviews·Vinod K TiwariXi Chen
Apr 18, 2016·Carbohydrate Research·Xiao-Peng HeGuo-Rong Chen
Mar 16, 2012·Future Medicinal Chemistry·Rachel Hevey, Chang-Chun Ling
Jul 4, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Qingjiang Li, Zhongwu Guo
Jun 18, 2017·Medicinal Research Reviews·Jian Gao, Zhongwu Guo
Feb 2, 2021·Nature Reviews. Chemistry·Carlo PifferiAlberto Fernández-Tejada
Dec 18, 2020·Frontiers in Chemistry·Biswajit Sarkar, Narayanaswamy Jayaraman
Oct 9, 2020·Carbohydrate Research·Enrico C J M VerpalenGeert-Jan Boons
Jun 25, 2021·Chemical Reviews·Anand K AgrahariVinod K Tiwari
Jan 30, 2018·Bioconjugate Chemistry·Bob J IgnacioMartijn Verdoes

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