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Synthesis of next generation maleimide radical labels

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NGMSL_Synlett_accepted.pdf (549.2Kb)
Date
10/2016
Author
Hajjaj, Bouchra
Shah, Anokhi
Bell, Stacey
Shirran, Sally Lorna
Botting, Catherine Helen
Slawin, Alexandra Martha Zoya
Hulme, Alison
Lovett, Janet Eleanor
Keywords
Next-generation maleimide
Succinimide
Nitroxide spin label
Radical
EPR spectroscopy
QC Physics
QD Chemistry
DAS
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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.
Citation
Hajjaj , B , Shah , A , Bell , S , Shirran , S L , Botting , C H , Slawin , A M Z , Hulme , A & Lovett , J E 2016 , ' Synthesis of next generation maleimide radical labels ' , Synlett , pp. 2357-2361 . https://doi.org/10.1055/s-0035-1562451
Publication
Synlett
Status
Peer reviewed
DOI
https://doi.org/10.1055/s-0035-1562451
ISSN
0936-5214
Type
Journal article
Rights
© 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
Description
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.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/11153

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