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A water-soluble ruthenium glycosylated porphyrin catalyst for carbenoid transfer reactions in aqueous media with applications in bioconjugation reactions.
J Am Chem Soc. 2010 Feb 17; 132(6):1886-94.JA

Abstract

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 approximately 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.

Authors+Show Affiliations

Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, PR China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20088517

Citation

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, vol. 132, no. 6, 2010, pp. 1886-94.
Ho CM, Zhang JL, Zhou CY, et al. A water-soluble ruthenium glycosylated porphyrin catalyst for carbenoid transfer reactions in aqueous media with applications in bioconjugation reactions. J Am Chem Soc. 2010;132(6):1886-94.
Ho, C. M., Zhang, J. L., Zhou, C. Y., Chan, O. Y., Yan, J. J., Zhang, F. Y., Huang, J. S., & Che, C. M. (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, 132(6), 1886-94. https://doi.org/10.1021/ja9077254
Ho CM, et al. A Water-soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media With Applications in Bioconjugation Reactions. J Am Chem Soc. 2010 Feb 17;132(6):1886-94. PubMed PMID: 20088517.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A water-soluble ruthenium glycosylated porphyrin catalyst for carbenoid transfer reactions in aqueous media with applications in bioconjugation reactions. AU - Ho,Chi-Ming, AU - Zhang,Jun-Long, AU - Zhou,Cong-Ying, AU - Chan,On-Yee, AU - Yan,Jessie Jing, AU - Zhang,Fu-Yi, AU - Huang,Jie-Sheng, AU - Che,Chi-Ming, PY - 2010/1/22/entrez PY - 2010/1/22/pubmed PY - 2010/4/30/medline SP - 1886 EP - 94 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 6 N2 - 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 approximately 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. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20088517/A_water_soluble_ruthenium_glycosylated_porphyrin_catalyst_for_carbenoid_transfer_reactions_in_aqueous_media_with_applications_in_bioconjugation_reactions_ DB - PRIME DP - Unbound Medicine ER -