A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid   Transfer Reactions in Aqueous Media with Applications in Bioconjugation   Reactions

doi:10.1021/ja9077254

CORC > 北京大学 > 化学与分子工程学院

	A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media with Applications in Bioconjugation Reactions
	Ho, Chi-Ming ; Zhang, Jun-Long ; Zhou, Cong-Ying ; Chan, On-Yee ; Yan, Jessie Jing ; Zhang, Fu-Yi ; Huang, Jie-Sheng ; Che, Chi-Ming
刊名	journal of the american chemical society
	2010
关键词	C-H INSERTION MANGANESE-GLYCOCONJUGATED PORPHYRINS RAY CRYSTAL-STRUCTURE ALPHA-AMINO-ACIDS N-H ASYMMETRIC CYCLOPROPANATION ETHYL DIAZOACETATE RHODIUM CARBENOIDS ORGANIC-SYNTHESIS IRON PORPHYRINS
DOI	10.1021/ja9077254
英文摘要	Water-soluble [Ru-II(4-Glc-TPP)(CO)] (1, 4-Glc-TPP = meso-tetrakis(4-(beta-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 fluorescent-labeled diazoacetate 15 in the presence of a catalytic amount of 1. The corresponding cyclopropanation product (24) was obtained with similar to 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; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000275085000051&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Chemistry, Multidisciplinary; SCI(E); EI; 46; ARTICLE; 6; 1886-1894; 132
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/244845]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Ho, Chi-Ming,Zhang, Jun-Long,Zhou, Cong-Ying,et al. A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media with Applications in Bioconjugation Reactions[J]. journal of the american chemical society,2010.
APA	Ho, Chi-Ming.,Zhang, Jun-Long.,Zhou, Cong-Ying.,Chan, On-Yee.,Yan, Jessie Jing.,...&Che, Chi-Ming.(2010).A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media with Applications in Bioconjugation Reactions.journal of the american chemical society.
MLA	Ho, Chi-Ming,et al."A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media with Applications in Bioconjugation Reactions".journal of the american chemical society (2010).