Literature DB >> 24123634

Thiols and selenols as electron-relay catalysts for disulfide-bond reduction.

John C Lukesh1, Brett Vanveller, Ronald T Raines.   

Abstract

Pass them on! Dithiobutylamine immobilized on a resin is a useful reagent for the reduction of disulfide bonds. Its ability to reduce a disulfide bond in a protein is enhanced greatly if used along with a soluble strained cyclic disulfide or mixed diselenide that relays electrons from the resin to the protein. This electron-relay catalysis system provides distinct advantages over the use of excess soluble reducing agent alone.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  heterogeneous catalysis; proteins; redox chemistry; selenium; sulfur

Mesh:

Substances:

Year:  2013        PMID: 24123634      PMCID: PMC3885359          DOI: 10.1002/anie.201307481

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  40 in total

1.  Labeling of antibodies by in situ modification of thiol groups generated from selenol-catalyzed reduction of native disulfide bonds.

Authors:  Rajeeva Singh; Erin K Maloney
Journal:  Anal Biochem       Date:  2002-05-15       Impact factor: 3.365

2.  The segmented anisotropic refinement of monoclinic papain by the application of the rigid-body TLS model and comparison to bovine ribonuclease A.

Authors:  G W Harris; R W Pickersgill; B Howlin; D S Moss
Journal:  Acta Crystallogr B       Date:  1992-02-01

3.  Electron transfer in peptides with cysteine and methionine as relay amino acids.

Authors:  Min Wang; Jian Gao; Pavel Müller; Bernd Giese
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 4.  Differing views of the role of selenium in thioredoxin reductase.

Authors:  Robert J Hondal; Erik L Ruggles
Journal:  Amino Acids       Date:  2010-02-21       Impact factor: 3.520

5.  Structure and properties of TentaGel resin beads: implications for combinatorial library chemistry.

Authors:  R Quarrell; T D Claridge; G W Weaver; G Lowe
Journal:  Mol Divers       Date:  1996-08       Impact factor: 2.943

6.  On the size of the active site in proteases. I. Papain.

Authors:  I Schechter; A Berger
Journal:  Biochem Biophys Res Commun       Date:  1967-04-20       Impact factor: 3.575

7.  Diselenides as universal oxidative folding catalysts of diverse proteins.

Authors:  Joris Beld; Kenneth J Woycechowsky; Donald Hilvert
Journal:  J Biotechnol       Date:  2010-10-08       Impact factor: 3.307

8.  Catalytic selenols couple the redox cycles of metallothionein and glutathione.

Authors:  Y Chen; W Maret
Journal:  Eur J Biochem       Date:  2001-06

9.  Selenium and sulfur in exchange reactions: a comparative study.

Authors:  Daniel Steinmann; Thomas Nauser; Willem H Koppenol
Journal:  J Org Chem       Date:  2010-10-01       Impact factor: 4.354

10.  Reaction of Tris(2-carboxyethyl)phosphine (TCEP) with maleimide and alpha-haloacyl groups: anomalous elution of TCEP by gel filtration.

Authors:  D E Shafer; J K Inman; A Lees
Journal:  Anal Biochem       Date:  2000-06-15       Impact factor: 3.365

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  6 in total

1.  Pyrazine-derived disulfide-reducing agent for chemical biology.

Authors:  John C Lukesh; Kelly K Wallin; Ronald T Raines
Journal:  Chem Commun (Camb)       Date:  2014-08-28       Impact factor: 6.222

2.  Cyclic Thiosulfonates for Thiol-Mediated Uptake: Cascade Exchangers, Transporters, Inhibitors.

Authors:  Takehiro Kato; Bumhee Lim; Yangyang Cheng; Anh-Tuan Pham; John Maynard; Dimitri Moreau; Amalia I Poblador-Bahamonde; Naomi Sakai; Stefan Matile
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3.  Diselenolane-mediated cellular uptake.

Authors:  Nicolas Chuard; Amalia I Poblador-Bahamonde; Lili Zong; Eline Bartolami; Jana Hildebrandt; Wolfgang Weigand; Naomi Sakai; Stefan Matile
Journal:  Chem Sci       Date:  2018-01-17       Impact factor: 9.825

4.  High efficiency reduction capability for the formation of Fab׳ antibody fragments from F(ab)2 units.

Authors:  Victor Crivianu-Gaita; Alexander Romaschin; Michael Thompson
Journal:  Biochem Biophys Rep       Date:  2015-04-25

5.  An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates.

Authors:  Quentin Laurent; Naomi Sakai; Stefan Matile
Journal:  Chemistry       Date:  2022-05-04       Impact factor: 5.020

6.  Inhibitors of thiol-mediated uptake.

Authors:  Yangyang Cheng; Anh-Tuan Pham; Takehiro Kato; Bumhee Lim; Dimitri Moreau; Javier López-Andarias; Lili Zong; Naomi Sakai; Stefan Matile
Journal:  Chem Sci       Date:  2020-11-18       Impact factor: 9.825

  6 in total

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