Synthesis of next generation maleimide radical labels

Bouchra Hajjaj; Anokhi Shah; Stacey Bell; Sally Lorna Shirran; Catherine Helen Botting; Alexandra Martha Zoya Slawin; Alison Hulme; Janet Eleanor Lovett

doi:10.1055/s-0035-1562451

Synthesis of next generation maleimide radical labels

Bouchra Hajjaj, Anokhi Shah, Stacey Bell, Sally Lorna Shirran, Catherine Helen Botting, Alexandra Martha Zoya Slawin, Alison Hulme, Janet Eleanor Lovett

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

Abstract

The synthesis and characterization of four new nitroxide-radical-containing next-generation maleimides are presented. Each new label has a single leaving group which is either a phenoxyl or bromide. The linker between the maleimide and the nitroxide-containing framework is either a racemic mixture of a short chain or an achiral longer chain. These molecules have been designed to site-specifically label vicinal cysteines in proteins for magnetic resonance studies. The characterization of the final products includes crystallography and the labeling of sperm whale myoglobin protein.

Original language	English
Article number	27
Pages (from-to)	2357-2361
Number of pages	5
Journal	Synlett
Early online date	5 Jul 2016
DOIs	https://doi.org/10.1055/s-0035-1562451
Publication status	Published - Oct 2016

Keywords

Next-generation maleimide
Succinimide
Nitroxide spin label
Radical
EPR spectroscopy

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10.1055/s-0035-1562451

NGMSL Synlett accepted
© 2016, Georg Thieme. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at www.thieme-connect.de / https://dx.doi.org/10.1055/s-0035-1562451
Accepted author manuscript, 549 KB

New Strategies for Spin Labelling: New strategies for spin labelling cysteine-rich proteins
Lovett, J. E. (PI)
EPSRC
1/09/14 → 31/08/15
Project: Standard
Royal Society Research Fellowship: Royal Society Research Fellowship
Lovett, J. E. (PI)
The Royal Society
1/05/14 → 15/02/17
Project: Fellowship

Data underpinning - Synthesis of Next Generation Maleimide Radical Labels
Hajjaj, B. (Creator), Shah, A. (Creator), Bell, S. (Creator), Shirran, S. L. (Creator), Botting, C. H. (Creator), Slawin, A. M. Z. (Creator), Hulme, A. (Creator) & Lovett, J. E. (Creator), University of St Andrews, 3 Aug 2016
DOI: 10.17630/19ac1929-f829-449b-adee-323baeedf0e5
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@article{2015c6bd6e3f4d88bf565d1aeae2a168,

title = "Synthesis of next generation maleimide radical labels",

abstract = "The synthesis and characterization of four new nitroxide-radical-containing next-generation maleimides are presented. Each new label has a single leaving group which is either a phenoxyl or bromide. The linker between the maleimide and the nitroxide-containing framework is either a racemic mixture of a short chain or an achiral longer chain. These molecules have been designed to site-specifically label vicinal cysteines in proteins for magnetic resonance studies. The characterization of the final products includes crystallography and the labeling of sperm whale myoglobin protein.",

keywords = "Next-generation maleimide, Succinimide, Nitroxide spin label, Radical, EPR spectroscopy",

author = "Bouchra Hajjaj and Anokhi Shah and Stacey Bell and Shirran, {Sally Lorna} and Botting, {Catherine Helen} and Slawin, {Alexandra Martha Zoya} and Alison Hulme and Lovett, {Janet Eleanor}",

note = "This work was funded by EPSRC, Grant Number EP/LO22044/1, a Royal Society University Research Fellowship to JEL , Royal Society Research Grant RG120645 and support from Active Spectrum Inc.",

year = "2016",

month = oct,

doi = "10.1055/s-0035-1562451",

language = "English",

pages = "2357--2361",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Synthesis of next generation maleimide radical labels

AU - Hajjaj, Bouchra

AU - Shah, Anokhi

AU - Bell, Stacey

AU - Shirran, Sally Lorna

AU - Botting, Catherine Helen

AU - Slawin, Alexandra Martha Zoya

AU - Hulme, Alison

AU - Lovett, Janet Eleanor

N1 - This work was funded by EPSRC, Grant Number EP/LO22044/1, a Royal Society University Research Fellowship to JEL , Royal Society Research Grant RG120645 and support from Active Spectrum Inc.

PY - 2016/10

Y1 - 2016/10

N2 - The synthesis and characterization of four new nitroxide-radical-containing next-generation maleimides are presented. Each new label has a single leaving group which is either a phenoxyl or bromide. The linker between the maleimide and the nitroxide-containing framework is either a racemic mixture of a short chain or an achiral longer chain. These molecules have been designed to site-specifically label vicinal cysteines in proteins for magnetic resonance studies. The characterization of the final products includes crystallography and the labeling of sperm whale myoglobin protein.

AB - The synthesis and characterization of four new nitroxide-radical-containing next-generation maleimides are presented. Each new label has a single leaving group which is either a phenoxyl or bromide. The linker between the maleimide and the nitroxide-containing framework is either a racemic mixture of a short chain or an achiral longer chain. These molecules have been designed to site-specifically label vicinal cysteines in proteins for magnetic resonance studies. The characterization of the final products includes crystallography and the labeling of sperm whale myoglobin protein.

KW - Next-generation maleimide

KW - Succinimide

KW - Nitroxide spin label

KW - Radical

KW - EPR spectroscopy

U2 - 10.1055/s-0035-1562451

DO - 10.1055/s-0035-1562451

M3 - Article

SN - 0936-5214

SP - 2357

EP - 2361

JO - Synlett

JF - Synlett

M1 - 27

ER -

Synthesis of next generation maleimide radical labels

Abstract

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Projects

New Strategies for Spin Labelling: New strategies for spin labelling cysteine-rich proteins

Royal Society Research Fellowship: Royal Society Research Fellowship

Datasets

Data underpinning - Synthesis of Next Generation Maleimide Radical Labels

Cite this