Reductive Alkylation of Proteins Using Iridium Catalyzed Transfer Hydrogenation
- 8 September 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (39) , 13490-13491
- https://doi.org/10.1021/ja054686c
Abstract
An efficient transition metal catalyzed procedure for the reductive alkylation of proteins has been developed. Imines formed from the condensation of aldehydes (1 mM) with lysine residues and the N-terminus can be reduced efficiently by a [Cp*Ir(4,4‘-dimethoxy-2,2‘-bipyridine)(H2O)]SO4 catalyst in the presence of formate ions. The reaction proceeds readily at pH 7.4 in aqueous phosphate buffer at temperatures ranging from 22 to 37 °C, and reaches high levels of conversion for a number of aromatic aldehydes. UV experiments have confirmed that the catalyst does not bind to protein substrates. The utility of the reaction has been demonstrated through an efficient two-step procedure for the attachment of unfunctionalized poly(ethylene glycol) to protein targets.Keywords
This publication has 11 references indexed in Scilit:
- Suzuki coupling for protein modificationTetrahedron Letters, 2005
- pH-Selective Synthesis and Structures of Alkynyl, Acyl, and Ketonyl Intermediates in Anti-Markovnikov and Markovnikov Hydrations of a Terminal Alkyne with a Water-Soluble Iridium Aqua Complex in WaterJournal of the American Chemical Society, 2004
- Selective Tryptophan Modification with Rhodium Carbenoids in Aqueous SolutionJournal of the American Chemical Society, 2004
- Determining the Geometries of Transition States by Use of Antihydrophobic Additives in WaterAccounts of Chemical Research, 2004
- pH-Dependent Chemoselective Synthesis of α-Amino Acids. Reductive Amination of α-Keto Acids with Ammonia Catalyzed by Acid-Stable Iridium Hydride Complexes in WaterJournal of the American Chemical Society, 2004
- Half-Sandwich Complexes with 4,7-Dihydroxy-1,10-phenanthroline: Water-Soluble, Highly Efficient Catalysts for Hydrogenation of Bicarbonate Attributable to the Generation of an Oxyanion on the Catalyst LigandOrganometallics, 2004
- Activity-Based Protein Profiling in Vivo Using a Copper(I)-Catalyzed Azide-Alkyne [3 + 2] CycloadditionJournal of the American Chemical Society, 2003
- Isolation and Crystal Structure of a Water-Soluble Iridium Hydride: A Robust and Highly Active Catalyst for Acid-Catalyzed Transfer Hydrogenations of Carbonyl Compounds in Acidic MediaJournal of the American Chemical Society, 2003
- Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] CycloadditionJournal of the American Chemical Society, 2003
- .pi.-Arene Aqua Complexes of Cobalt, Rhodium, Iridium, and Ruthenium: Preparation, Structure, and Kinetics of Water Exchange and Water SubstitutionInorganic Chemistry, 1995