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Article: A water-soluble ruthenium glycosylated porphyrin catalyst for carbenoid transfer reactions in aqueous media with applications in bioconjugation reactions

TitleA water-soluble ruthenium glycosylated porphyrin catalyst for carbenoid transfer reactions in aqueous media with applications in bioconjugation reactions
Authors
Issue Date2010
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 2010, v. 132 n. 6, p. 1886-1894 How to Cite?
AbstractWater-soluble [RuII(4-Glc-TPP)(CO)] (1, 4-Glc-TPP ) = meso-tetrakis(4-(β-D-glucosyl)phenyl)porphyrinato dianion) is an active catalyst for the following carbenoid transfer reactions in aqueous media with good selectivities and up to 100% conversions: intermolecular cyclopropanation of styrenes (up to 76% yield), intramolecular cyclopropanation of an allylic diazoacetate (68% yield), intramolecular ammonium/ sulfonium ylide formation/[2,3]-sigmatroptic rearrangement reactions (up to 91% yield), and intermolecular carbenoid insertion into N-H bonds of primary arylamines (up to 83% yield). This ruthenium glycosylated porphyrin complex can selectively catalyze alkylation of the N-terminus of peptides (8 examples) and mediate N-terminal modification of proteins (four examples) using a fluorescent-tethered diazo compound (15). A fluorescent group was conjugated to ubiquitin via 1-catalyzed alkene cyclopropanation with 15 in aqueous solution in two steps: (1) incorporation of an alkenic group by the reaction of N-hydroxysuccinimide ester 19 with ubiquitin and (2) cyclopropanation of the alkene-tethered Lys 6 ubiquitin (23) with the fluorescentlabeled diazoacetate 15 in the presence of a catalytic amount of 1. The corresponding cyclopropanation product (24) was obtained with -55% conversion based on MALDI-TOF mass spectrometry. The products 23, 24, and the N-terminal modified peptides and proteins were characterized by LC-MS/MS and/or SDS-PAGE analyses. © 2010 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/69335
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
Funding AgencyGrant Number
University of Hong Kong
University Grants Council of HKSARAoE 10/01P
Hong Kong Research Grants CouncilHKU 1/CRF/08
Funding Information:

This work was supported by The University of Hong Kong (University Development Fund), the University Grants Council of HKSAR (the Area of Excellence Scheme AoE 10/01P). and the Hong Kong Research Grants Council (HKU 1/CRF/08)

References

 

DC FieldValueLanguage
dc.contributor.authorHo, CMen_HK
dc.contributor.authorZhang, JLen_HK
dc.contributor.authorZhou, CYen_HK
dc.contributor.authorChan, OYen_HK
dc.contributor.authorYan, JJen_HK
dc.contributor.authorZhang, FYen_HK
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:12:43Z-
dc.date.available2010-09-06T06:12:43Z-
dc.date.issued2010en_HK
dc.identifier.citationJournal Of The American Chemical Society, 2010, v. 132 n. 6, p. 1886-1894en_HK
dc.identifier.issn0002-7863en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69335-
dc.description.abstractWater-soluble [RuII(4-Glc-TPP)(CO)] (1, 4-Glc-TPP ) = meso-tetrakis(4-(β-D-glucosyl)phenyl)porphyrinato dianion) is an active catalyst for the following carbenoid transfer reactions in aqueous media with good selectivities and up to 100% conversions: intermolecular cyclopropanation of styrenes (up to 76% yield), intramolecular cyclopropanation of an allylic diazoacetate (68% yield), intramolecular ammonium/ sulfonium ylide formation/[2,3]-sigmatroptic rearrangement reactions (up to 91% yield), and intermolecular carbenoid insertion into N-H bonds of primary arylamines (up to 83% yield). This ruthenium glycosylated porphyrin complex can selectively catalyze alkylation of the N-terminus of peptides (8 examples) and mediate N-terminal modification of proteins (four examples) using a fluorescent-tethered diazo compound (15). A fluorescent group was conjugated to ubiquitin via 1-catalyzed alkene cyclopropanation with 15 in aqueous solution in two steps: (1) incorporation of an alkenic group by the reaction of N-hydroxysuccinimide ester 19 with ubiquitin and (2) cyclopropanation of the alkene-tethered Lys 6 ubiquitin (23) with the fluorescentlabeled diazoacetate 15 in the presence of a catalytic amount of 1. The corresponding cyclopropanation product (24) was obtained with -55% conversion based on MALDI-TOF mass spectrometry. The products 23, 24, and the N-terminal modified peptides and proteins were characterized by LC-MS/MS and/or SDS-PAGE analyses. © 2010 American Chemical Society.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_HK
dc.relation.ispartofJournal of the American Chemical Societyen_HK
dc.subject.meshAlkenes - chemistry-
dc.subject.meshGlycosylation-
dc.subject.meshMetalloporphyrins - chemistry-
dc.subject.meshRuthenium - chemistry-
dc.subject.meshWater - chemistry-
dc.titleA water-soluble ruthenium glycosylated porphyrin catalyst for carbenoid transfer reactions in aqueous media with applications in bioconjugation reactionsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0002-7863&volume=132&issue=6&spage=1886&epage=1894&date=2010&atitle=A+water-soluble+ruthenium+glycosylated+porphyrin+catalyst+for+carbenoid+transfer+reactions+in+aqueous+media+with+applications+in+bioconjugation+reactionsen_HK
dc.identifier.emailHo, CM: rickyho@hkucc.hku.hken_HK
dc.identifier.emailZhou, CY: cyzhou@hku.hken_HK
dc.identifier.emailHuang, JS: jshuang@hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hken_HK
dc.identifier.authorityHo, CM=rp00705en_HK
dc.identifier.authorityZhou, CY=rp00843en_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja9077254en_HK
dc.identifier.pmid20088517-
dc.identifier.scopuseid_2-s2.0-77249158404en_HK
dc.identifier.hkuros168985en_HK
dc.identifier.hkuros204504-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-77249158404&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume132en_HK
dc.identifier.issue6en_HK
dc.identifier.spage1886en_HK
dc.identifier.epage1894en_HK
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000275085000051-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridHo, CM=12807243800en_HK
dc.identifier.scopusauthoridZhang, JL=7601343511en_HK
dc.identifier.scopusauthoridZhou, CY=35742480200en_HK
dc.identifier.scopusauthoridChan, OY=36025013200en_HK
dc.identifier.scopusauthoridYan, JJ=35752634300en_HK
dc.identifier.scopusauthoridZhang, FY=7404970654en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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