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Article: Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containlng peptides in aqueous medium

TitleElectron-deficient alkynes as cleavable reagents for the modification of cysteine-containlng peptides in aqueous medium
Authors
KeywordsAlkynes
Chemoselectivity
Cleavage reactions
Cysteine
Peptides
Issue Date2009
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2009, v. 15 n. 15, p. 3839-3850 How to Cite?
AbstractAn efficient method has been developed for the chemoselective cysteine modification of unprotected peptides and proteins in aqueous media through the formation of a vinyl sulfide linkage by using electron-deficient alkynes, including alkynoic amides, esters and alkynones. The terminal alkynone-modified peptides could be converted back into the unmodified peptides (81 % isolated yield) by adding thiols under mild conditions. The usefulness of this thiol-assisted cleavage of the vinyl sulfide linkage in peptides has been exemplified by the enrichment of a cysteine-containing peptide (71% recovery) from a mixture of cysteine-containing and non-cysteine-containing peptides. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Persistent Identifierhttp://hdl.handle.net/10722/135048
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
Funding AgencyGrant Number
The University of Hong Kong
Area of Excellence SchemeAoE/P-10-01
Research Grants Council (HKSAR)HKU 7052/07P
Funding Information:

This work was supported by The University of Hong Kong (University Development Fund) and the Area of Excellence Scheme (AoE/P-10-01) established under the University Grants Committee (HKSAR) and the Research Grants Council (HKSAR) (HKU 7052/07P). We thank Dr. W.-H. Cheung for providing some of the peptide samples and Dr. C.-N. Lok for providing advice and materials for the peptide enrichment experiment. We thank the reviewers for their helpful comments and suggestions.

References

 

DC FieldValueLanguage
dc.contributor.authorShiu, HYen_HK
dc.contributor.authorChan, TCen_HK
dc.contributor.authorHo, CMen_HK
dc.contributor.authorLiu, Yen_HK
dc.contributor.authorWong, MKen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2011-07-27T01:27:09Z-
dc.date.available2011-07-27T01:27:09Z-
dc.date.issued2009en_HK
dc.identifier.citationChemistry - A European Journal, 2009, v. 15 n. 15, p. 3839-3850en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/135048-
dc.description.abstractAn efficient method has been developed for the chemoselective cysteine modification of unprotected peptides and proteins in aqueous media through the formation of a vinyl sulfide linkage by using electron-deficient alkynes, including alkynoic amides, esters and alkynones. The terminal alkynone-modified peptides could be converted back into the unmodified peptides (81 % isolated yield) by adding thiols under mild conditions. The usefulness of this thiol-assisted cleavage of the vinyl sulfide linkage in peptides has been exemplified by the enrichment of a cysteine-containing peptide (71% recovery) from a mixture of cysteine-containing and non-cysteine-containing peptides. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.en_HK
dc.languageengen_US
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistryen_HK
dc.relation.ispartofChemistry - A European Journalen_HK
dc.subjectAlkynesen_HK
dc.subjectChemoselectivityen_HK
dc.subjectCleavage reactionsen_HK
dc.subjectCysteineen_HK
dc.subjectPeptidesen_HK
dc.subject.meshAlbumins - chemistry-
dc.subject.meshAlkynes - chemistry-
dc.subject.meshCysteine - chemistry-
dc.subject.meshElectrons-
dc.subject.meshPeptides - chemistry-
dc.titleElectron-deficient alkynes as cleavable reagents for the modification of cysteine-containlng peptides in aqueous mediumen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0947-6539&volume=15&issue=15&spage=3839–3850&epage=&date=2009&atitle=Electron-deficient+alkynes+as+cleavable+reagents+for+the+modification+of+cysteine-containing+peptides+in+aqueous+medium-
dc.identifier.emailHo, CM: rickyho@hkucc.hku.hken_HK
dc.identifier.emailLiu, Y: lyg100@hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hken_HK
dc.identifier.authorityHo, CM=rp00705en_HK
dc.identifier.authorityLiu, Y=rp00749en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.200800669en_HK
dc.identifier.pmid19229937en_HK
dc.identifier.scopuseid_2-s2.0-63849141606en_HK
dc.identifier.hkuros188102en_US
dc.identifier.hkuros155952-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-63849141606&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume15en_HK
dc.identifier.issue15en_HK
dc.identifier.spage3839en_HK
dc.identifier.epage3850en_HK
dc.identifier.isiWOS:000265162900026-
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridShiu, HY=6602861753en_HK
dc.identifier.scopusauthoridChan, TC=35119958300en_HK
dc.identifier.scopusauthoridHo, CM=12807243800en_HK
dc.identifier.scopusauthoridLiu, Y=8225912600en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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