Design and synthesis of cysteine-specific labels for photo-crosslinking studies. Issue 14 (7th March 2019)

• Record Type: Journal Article
• Authors: Walko, Martin; Hewitt, Eric; Radford, Sheena E.; Wilson, Andrew J.
• Is Part Of: RSC advances. Volume 9:Issue 14(2019)
• Page Start: 7610
• Page End: 7614
• Publication Date: 2019-03-07
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8ra10436k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : The design and synthesis of cysteine specific diazirine containing labels is described. Abstract : Chemical cross-linking mass-spectrometry (XL-MS) represents a powerful methodology to map ligand/biomacromolecule interactions, particularly where conventional methods such as X-ray crystallography, nuclear magnetic resonance (NMR) spectroscopy or cryo-electron microscopy (EM) are not feasible. In this manuscript, we describe the design and synthesis of two new photo-crosslinking reagents that can be used to specifically label free thiols through either maleimido or methanethiosulfonate groups and facilitate PXL-MS workflows. Both crosslinkers are based on light sensitive diazirines – precursors of highly reactive carbenes which offer additional advantages over alternative crosslinking groups such as benzophenones and aryl nitrenes given the controlled rapid and more indiscriminate reactivity.