Chemoenzymatic Assembly of Bacterial Glycoconjugates for Site-Specific Orthogonal Labeling

Journal of the American Chemical Society
Vinita LukoseBarbara Imperiali

Abstract

The cell surfaces of bacteria are replete with diverse glycoconjugates that play pivotal roles in determining how bacteria interact with the environment and the hosts that they colonize. Studies to advance our understanding of these interactions rely on the availability of chemically defined glycoconjugates that can be selectively modified under orthogonal reaction conditions to serve as discrete ligands to probe biological interactions, in displayed arrays and as imaging agents. Herein, enzymes in the N-linked protein glycosylation (Pgl) pathway of Campylobacter jejuni are evaluated for their tolerance for azide-modified UDP-sugar substrates, including derivatives of 2,4-diacetamidobacillosamine and N-acetylgalactosamine. In vitro analyses reveal that chemoenzymatic approaches are useful for the preparation of undecaprenol diphosphate-linked glycans and glycopeptides with site-specific introduction of azide functionality for orthogonal labeling at three specific sites in the heptasaccharide glycan. The uniquely modified glycoconjugates represent valuable tools for investigating the roles of C. jejuni cell surface glycoconjugates in host pathogen interactions.

References

Jul 19, 2002·Molecular Microbiology·Inga Benz, M Alexander Schmidt
Jun 5, 2003·Trends in Microbiology·Christine M SzymanskiBrendan W Wren
Oct 29, 2003·Current Opinion in Chemical Biology·Danielle H Dube, Carolyn R Bertozzi
Sep 28, 2005·Proceedings of the National Academy of Sciences of the United States of America·Kerney Jebrell GloverBarbara Imperiali
Apr 28, 2006·Proceedings of the National Academy of Sciences of the United States of America·Michael WackerMarkus Aebi
Apr 2, 2010·Nature Reviews. Drug Discovery·Rena D Astronomo, Dennis R Burton
Oct 16, 2010·Nature Reviews. Microbiology·Harald Nothaft, Christine M Szymanski
Feb 9, 2011·Proceedings of the National Academy of Sciences of the United States of America·Michael BoyceCarolyn R Bertozzi
Sep 1, 2011·The Journal of Biological Chemistry·Isabelle HugMario F Feldman
Mar 14, 2012·Proceedings of the National Academy of Sciences of the United States of America·Seok-Ho YuJennifer J Kohler
Jan 1, 2014·Journal of the American Chemical Society·Feng LiuBenjamin G Davis
Mar 22, 2014·Chemical Communications : Chem Comm·Van N Tra, Danielle H Dube
May 13, 2014·Nature Chemical Biology·Sean R StowellRichard D Cummings
Sep 4, 2014·Microbiology and Molecular Biology Reviews : MMBR·Hanne L P Tytgat, Sarah Lebeer

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Citations

Mar 10, 2017·Trends in Biotechnology·Timo Johannssen, Bernd Lepenies
Nov 16, 2019·Chembiochem : a European Journal of Chemical Biology·Zhenrun J ZhangHoward C Hang
Aug 25, 2018·Chemical Reviews·Chao Li, Lai-Xi Wang
Feb 27, 2016·Journal of the American Chemical Society·Monika Musial-SiwekBarbara Imperiali

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Methods Mentioned

BETA
glycosylation
electrophoresis

Related Concepts

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Campylobacteriosis (ASM)

Campylobacteriosis is caused by the bacteria Campylobacter jejuni and is a common cause of gastroenteritis in humans. Discover the latest research on Campylobacteriosis here.