Imperial College London
Alternate

ProfessorAlanArmstrong

Faculty of Natural Sciences, Department of Chemistry

Professor of Organic Synthesis
 
 
 
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Contact

 

+44 (0)20 7594 5876a.armstrong

 
 
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Location

 

501EMolecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@article{Craven:2019:10.1039/C8MD00566D,
author = {Craven, G and Affron, D and Raymond, P and Mann, D and Armstrong, A},
doi = {10.1039/C8MD00566D},
journal = {MedChemComm},
pages = {158--163},
title = {Vinyl sulfonamide synthesis for irreversible tethering via a novel α-selenoether protection strategy},
url = {http://dx.doi.org/10.1039/C8MD00566D},
volume = {10},
year = {2019}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - Vinyl sulfonamides are valuable electrophiles for targeted protein modification and inhibition. We describe a novel approach to the synthesis of terminal vinyl sulfonamides which uses mild oxidative conditions to induce elimination of an α-selenoether masking group. The method complements traditional synthetic approaches and typically yields vinyl sulfonamides in high purity after aqueous work-up without requiring column chromatography of the final electrophilic product. The methodology is applied to the synthesis of covalent fragments for use in irreversible protein tethering and crucially enables the attachment of diverse fragments to the vinyl sulfonamide warhead via a chemical linker. Using thymidylate synthase as a model system, ethylene glycol is identified as an effective linker for irreversible protein tethering.
AU  - Craven,G
AU  - Affron,D
AU  - Raymond,P
AU  - Mann,D
AU  - Armstrong,A
DO  - 10.1039/C8MD00566D
EP  - 163
PY  - 2019///
SN  - 2040-2503
SP  - 158
TI  - Vinyl sulfonamide synthesis for irreversible tethering via a novel α-selenoether protection strategy
T2  - MedChemComm
UR  - http://dx.doi.org/10.1039/C8MD00566D
UR  - http://hdl.handle.net/10044/1/66774
VL  - 10
ER  -
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