Design and synthesis of cysteine-specific labels for photo-crosslinking studies

Martin Walko; Eric Hewitt; Sheena E. Radford; Andrew J. Wilson

doi:10.1039/C8RA10436K

Design and synthesis of cysteine-specific labels for photo-crosslinking studies

Martin Walko, Eric Hewitt, Sheena E. Radford, Andrew J. Wilson^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7610-7614
Number of pages	5
Journal	RSC Advances
Volume	9
Issue number	14
DOIs	https://doi.org/10.1039/C8RA10436K
Publication status	Published - 2019

Bibliographical note

Funding Information:
The EPSRC (EP/N035267/1) are acknowledged for their support. S. E. R. acknowledges funding from the European Research Council under the European Union's Seventh Framework Programme grant FP7.2007-2013/grant agreement number 322408.

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1039/C8RA10436K

Cite this

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title = "Design and synthesis of cysteine-specific labels for photo-crosslinking studies",

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.",

author = "Martin Walko and Eric Hewitt and Radford, \{Sheena E.\} and Wilson, \{Andrew J.\}",

note = "Funding Information: The EPSRC (EP/N035267/1) are acknowledged for their support. S. E. R. acknowledges funding from the European Research Council under the European Union's Seventh Framework Programme grant FP7.2007-2013/grant agreement number 322408. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/C8RA10436K",

language = "English",

volume = "9",

pages = "7610--7614",

journal = "RSC Advances",

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publisher = "Royal Society of Chemistry",

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T1 - Design and synthesis of cysteine-specific labels for photo-crosslinking studies

AU - Walko, Martin

AU - Hewitt, Eric

AU - Radford, Sheena E.

AU - Wilson, Andrew J.

N1 - Funding Information: The EPSRC (EP/N035267/1) are acknowledged for their support. S. E. R. acknowledges funding from the European Research Council under the European Union's Seventh Framework Programme grant FP7.2007-2013/grant agreement number 322408. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85062839219

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DO - 10.1039/C8RA10436K

M3 - Article

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JO - RSC Advances

JF - RSC Advances

IS - 14

ER -

Design and synthesis of cysteine-specific labels for photo-crosslinking studies

Abstract

Bibliographical note

ASJC Scopus subject areas

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