Literature DB >> 21265534

Cupric superoxo-mediated intermolecular C-H activation chemistry.

Ryan L Peterson1, Richard A Himes, Hiroaki Kotani, Tomoyoshi Suenobu, Li Tian, Maxime A Siegler, Edward I Solomon, Shunichi Fukuzumi, Kenneth D Karlin.   

Abstract

The new cupric superoxo complex [LCu(II)(O(2)(•-))](+), which possesses particularly strong O-O and Cu-O bonding, is capable of intermolecular C-H activation of the NADH analogue 1-benzyl-1,4-dihydronicotinamide (BNAH). Kinetic studies indicated a first-order dependence on both the Cu complex and BNAH with a deuterium kinetic isotope effect (KIE) of 12.1, similar to that observed for certain copper monooxygenases.

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Year:  2011        PMID： 21265534      PMCID： PMC3091961          DOI： 10.1021/ja110466q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  32 in total

Review 1.  Reactivity of dioxygen-copper systems.

Authors:  Elizabeth A Lewis; William B Tolman
Journal:  Chem Rev       Date:  2004-02       Impact factor: 60.622

2.  Oxygen Binding, Activation, and Reduction to Water by Copper Proteins.

Authors:  Edward I. Solomon; Peng Chen; Markus Metz; Sang-Kyu Lee; Amy E. Palmer
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

3.  A 1:1 copper-dioxygen adduct is an end-on bound superoxo copper(II) complex which undergoes oxygenation reactions with phenols.

Authors:  Debabrata Maiti; H Christopher Fry; Julia S Woertink; Michael A Vance; Edward I Solomon; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

4.  Enzymatic C-H activation by metal-superoxo intermediates.

Authors:  J Martin Bollinger; Carsten Krebs
Journal:  Curr Opin Chem Biol       Date:  2007-03-19       Impact factor: 8.822

5.  The catalytic mechanism of peptidylglycine alpha-hydroxylating monooxygenase investigated by computer simulation.

Authors:  Alejandro Crespo; Marcelo A Martí; Adrian E Roitberg; L Mario Amzel; Darío A Estrin
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

6.  Copper-hydroperoxo-mediated N-debenzylation chemistry mimicking aspects of copper monooxygenases.

Authors:  Debabrata Maiti; Amy A Narducci Sarjeant; Kenneth D Karlin
Journal:  Inorg Chem       Date:  2008-09-11       Impact factor: 5.165

7.  Mononuclear Cu-O2 complexes: geometries, spectroscopic properties, electronic structures, and reactivity.

Authors:  Christopher J Cramer; William B Tolman
Journal:  Acc Chem Res       Date:  2007-04-26       Impact factor: 22.384

8.  Dioxygen binds end-on to mononuclear copper in a precatalytic enzyme complex.

Authors:  Sean T Prigge; Betty A Eipper; Richard E Mains; L Mario Amzel
Journal:  Science       Date:  2004-05-07       Impact factor: 47.728

9.  Evidence that dioxygen and substrate activation are tightly coupled in dopamine beta-monooxygenase. Implications for the reactive oxygen species.

Authors:  John P Evans; Kyunghye Ahn; Judith P Klinman
Journal:  J Biol Chem       Date:  2003-09-09       Impact factor: 5.157

10.  CopperII-mediated aromatic ortho-hydroxylation: a hybrid DFT and AB initio exploration.

Authors:  Peter Comba; Stefan Knoppe; Bodo Martin; Gopalan Rajaraman; Claudio Rolli; Brett Shapiro; Timon Stork
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
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  47 in total

1.  Intramolecular Hydrogen Bonding Enhances Stability and Reactivity of Mononuclear Cupric Superoxide Complexes.

Authors:  Mayukh Bhadra; Jung Yoon C Lee; Ryan E Cowley; Sunghee Kim; Maxime A Siegler; Edward I Solomon; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2018-07-13       Impact factor: 15.419

2.  Dioxygen Activation by a Macrocyclic Copper Complex Leads to a Cu2O2 Core with Unexpected Structure and Reactivity.

Authors:  Isaac Garcia-Bosch; Ryan E Cowley; Daniel E Díaz; Maxime A Siegler; Wonwoo Nam; Edward I Solomon; Kenneth D Karlin
Journal:  Chemistry       Date:  2016-02-26       Impact factor: 5.236

3.  Substrate and Lewis Acid Coordination Promote O-O Bond Cleavage of an Unreactive L2CuII2(O22-) Species to Form L2CuIII2(O)2 Cores with Enhanced Oxidative Reactivity.

Authors:  Isaac Garcia-Bosch; Ryan E Cowley; Daniel E Díaz; Ryan L Peterson; Edward I Solomon; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2017-02-14       Impact factor: 15.419

Review 4.  Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Authors:  Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal:  Chem Rev       Date:  2019-01-30       Impact factor: 60.622

5.  Reactivity of a stable copper-dioxygen complex.

Authors:  Diana A Iovan; Alexandra T Wrobel; Arthur A McClelland; Austin B Scharf; Guy A Edouard; Theodore A Betley
Journal:  Chem Commun (Camb)       Date:  2017-09-14       Impact factor: 6.222

Review 6.  Activation of Dioxygen by Iron and Manganese Complexes: A Heme and Nonheme Perspective.

Authors:  Sumit Sahu; David P Goldberg
Journal:  J Am Chem Soc       Date:  2016-08-30       Impact factor: 15.419

7.  Structure of the Reduced Copper Active Site in Preprocessed Galactose Oxidase: Ligand Tuning for One-Electron O2 Activation in Cofactor Biogenesis.

Authors:  Ryan E Cowley; Jordi Cirera; Munzarin F Qayyum; Dalia Rokhsana; Britt Hedman; Keith O Hodgson; David M Dooley; Edward I Solomon
Journal:  J Am Chem Soc       Date:  2016-09-28       Impact factor: 15.419

8.  Laser-Induced Dynamics of Peroxodicopper(II) Complexes Vary with the Ligand Architecture. One-Photon Two-Electron O2 Ejection and Formation of Mixed-Valent Cu(I)Cu(II)-Superoxide Intermediates.

Authors:  Claudio Saracini; Kei Ohkubo; Tomoyoshi Suenobu; Gerald J Meyer; Kenneth D Karlin; Shunichi Fukuzumi
Journal:  J Am Chem Soc       Date:  2015-12-11       Impact factor: 15.419

9.  Spin Interconversion of Heme-Peroxo-Copper Complexes Facilitated by Intramolecular Hydrogen-Bonding Interactions.

Authors:  Andrew W Schaefer; Melanie A Ehudin; David A Quist; Joel A Tang; Kenneth D Karlin; Edward I Solomon
Journal:  J Am Chem Soc       Date:  2019-03-14       Impact factor: 15.419

10.  Coordination chemistry and reactivity of a cupric hydroperoxide species featuring a proximal H-bonding substituent.

Authors:  Sunghee Kim; Claudio Saracini; Maxime A Siegler; Natalia Drichko; Kenneth D Karlin
Journal:  Inorg Chem       Date:  2012-11-15       Impact factor: 5.165
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