Synthesis of Rhamnosylated Arginine Glycopeptides and Determination of the Glycosidic Linkage in Bacterial Elongation Factor P

Authors

Siyao Wang, University of Sydney
Leo Corcilius, University of Sydney
Phillip B. Sharp, Walter and Eliza Hall Institute of Medical Research
Andrei Rajkovic, The Ohio State University
Michael Ibba, Chapman UniversityFollow
Benjamin L. Parker, University of Sydney
Richard J. Payne, University of Sydney

Document Type

Article

Publication Date

12-12-2016

Abstract

A new class of N-linked protein glycosylation – arginine rhamnosylation – has recently been discovered as a critical modification for the function of bacterial elongation factor P (EF-P). Herein, we describe the synthesis of suitably protected α- and β-rhamnosylated arginine amino acid “cassettes” that can be directly installed into rhamnosylated peptides. Preparation of a proteolytic fragment of Pseudomonas aeruginosa EF-P bearing both α- and β-rhamnosylated arginine enabled the unequivocal determination of the native glycosidic linkage to be α through 2D NMR and nano-UHPLC-tandem mass spectrometry studies.

Comments

This article was originally published in Chemical Science, volume 8, in 2017. https://doi.org/10.1039/C6SC03847F

Recommended Citation

Wang, S., Corcilius, L., Sharp, P.P., Rajkovic, A., Ibba, M., Parker, B.L. and Payne, R.J. (2017) Synthesis of rhamnosylated arginine glycopeptides and determination of the glycosidic linkage in bacterial elongation factor P. Chem. Sci. 8, 2296-2302. https://doi.org/10.1039/C6SC03847F

Copyright

Royal Society of Chemistry

Creative Commons License

This work is licensed under a Creative Commons Attribution 3.0 License.