Unexpected mechanochemical complexity: distinct reaction mechanisms in disulfide bond reduction in alkaline solution

Przemyslaw Dopieralski, Jordi Ribas–Arino, Padmesh Anjukandi, Martin Krupicka, and Dominik Marx (1) Lehrstuhl für Theoretische Chemie, Ruhr–Universität Bochum, 44780 Bochum, Germany (2) Permanent Address: Faculty of Chemistry, University of Wroclaw, Joliot–Curie 14, 50-383 Wroclaw, Poland (3) Current Address: Departament de Qúımica F́ısica and IQTCUB, Universitat de Barcelona, Av. Diagonal 645, 08028, Barcelona, Spain (4) Current Address: Max-Planck-Institut für Chemische Energiekoversion, Stiftstr. 34–36, 45470 Mülheim an der Ruhr, Germany

[1]  D. Marx,et al.  Force-Induced Reversal of β-Eliminations: Stressed Disulfide Bonds in Alkaline Solution. , 2016, Angewandte Chemie.

[2]  J. Oh,et al.  Recent Strategies to Develop Self‐Healable Crosslinked Polymeric Networks , 2015 .

[3]  R. Waymouth,et al.  Structurally dynamic hydrogels derived from 1,2-dithiolanes. , 2015, Journal of the American Chemical Society.

[4]  D. Marx,et al.  Disfavoring Mechanochemical Reactions by Stress-Induced Steric Hindrance. , 2015, Journal of chemical theory and computation.

[5]  D. Marx,et al.  The Effect of Tensile Stress on the Conformational Free Energy Landscape of Disulfide Bonds , 2014, PloS one.

[6]  F. Gräter,et al.  Identification of allosteric disulfides from prestress analysis. , 2014, Biophysical journal.

[7]  R. Boulatov,et al.  Model studies of force-dependent kinetics of multi-barrier reactions , 2013, Nature Communications.

[8]  D. Marx,et al.  The Janus-faced role of external forces in mechanochemical disulfide bond cleavage. , 2013, Nature chemistry.

[9]  P. Kosuri,et al.  Force dependency of biochemical reactions measured by single-molecule force-clamp spectroscopy , 2013, Nature Protocols.

[10]  R. J. Boyd,et al.  Revealing unexpected mechanisms for nucleophilic attack on S-S and Se-Se bridges. , 2013, Chemistry.

[11]  Canhui Lu,et al.  Mechanochemical devulcanization of ground tire rubber and its application in acoustic absorbent polyurethane foamed composites , 2013 .

[12]  R. Szoszkiewicz Single-molecule studies of disulfide bond reduction pathways used by human thioredoxin. , 2013, Biophysical chemistry.

[13]  CPMD simulation of a bimolecular chemical reaction: nucleophilic attack of a disulfide bond under mechanical stress. , 2012, Chemistry.

[14]  M. Siebert,et al.  Mechanism of thiolate-disulfide exchange: addition-elimination or effectively S(N)2? Effect of a shallow intermediate in gas-phase direct dynamics simulations. , 2012, The journal of physical chemistry. A.

[15]  D. Marx,et al.  Covalent mechanochemistry: theoretical concepts and computational tools with applications to molecular nanomechanics. , 2012, Chemical reviews.

[16]  F. Gräter,et al.  Mechanical force can fine-tune redox potentials of disulfide bonds. , 2012, Biophysical journal.

[17]  A. V. van Duin,et al.  Tunable nanomechanics of protein disulfide bonds in redox microenvironments. , 2012, Journal of the mechanical behavior of biomedical materials.

[18]  P. Kosuri,et al.  Direct observation of disulfide isomerization in a single protein , 2011, Nature chemistry.

[19]  D. Marx,et al.  Force-transformed free-energy surfaces and trajectory-shooting simulations reveal the mechano-stereochemistry of cyclopropane ring-opening reactions. , 2011, Angewandte Chemie.

[20]  R. Boulatov,et al.  Chemomechanics: chemical kinetics for multiscale phenomena. , 2011, Chemical Society reviews.

[21]  T. Helgaker,et al.  Influence of external force on properties and reactivity of disulfide bonds. , 2011, The journal of physical chemistry. A.

[22]  Julio M. Fernandez,et al.  Kinetic measurements on single-molecule disulfide bond cleavage. , 2011, Journal of the American Chemical Society.

[23]  S. Garcia-Manyes,et al.  Contrasting the individual reactive pathways in protein unfolding and disulfide bond reduction observed within a single protein. , 2011, Journal of the American Chemical Society.

[24]  Jeremy M. Lenhardt,et al.  From molecular mechanochemistry to stress-responsive materials , 2011 .

[25]  Luca De Gioia,et al.  Computational Organic Chemistry , 2011 .

[26]  F. Gräter,et al.  Atomistic evidence of how force dynamically regulates thiol/disulfide exchange. , 2010, Journal of the American Chemical Society.

[27]  I. Frank,et al.  Disulfide bond cleavage: a redox reaction without electron transfer. , 2010, Chemistry.

[28]  Amalendu Chandra,et al.  Aqueous basic solutions: hydroxide solvation, structural diffusion, and comparison to the hydrated proton. , 2010, Chemical reviews.

[29]  G. Whitesides,et al.  Thiol—disulfide interchange , 2010 .

[30]  G. Duan,et al.  A review of mechanochemistry applications in waste management. , 2010, Waste management.

[31]  M. A. Wouters,et al.  Disulfides as redox switches: from molecular mechanisms to functional significance. , 2010, Antioxidants & redox signaling.

[32]  Mary M. Caruso,et al.  Mechanically-induced chemical changes in polymeric materials. , 2009, Chemical reviews.

[33]  R. Boulatov,et al.  Kinetics of thiol/disulfide exchange correlate weakly with the restoring force in the disulfide moiety. , 2009, Angewandte Chemie.

[34]  Julio M. Fernandez,et al.  Mechanochemistry: one bond at a time. , 2009, ACS nano.

[35]  R. Szoszkiewicz,et al.  Force-activated reactivity switch in a bimolecular chemical reaction. , 2009, Nature chemistry.

[36]  D. Marx,et al.  Understanding covalent mechanochemistry. , 2009, Angewandte Chemie.

[37]  Sri Rama Koti Ainavarapu,et al.  Single-molecule force spectroscopy measurements of bond elongation during a bimolecular reaction. , 2008, Journal of the American Chemical Society.

[38]  C. Thorpe,et al.  Mechanism of thiolate-disulfide interchange reactions in biochemistry. , 2008, The Journal of organic chemistry.

[39]  Frauke Gräter,et al.  Probing the chemistry of thioredoxin catalysis with force , 2007, Nature.

[40]  H. Versteeg,et al.  Disulfide isomerization switches tissue factor from coagulation to cell signaling , 2006, Proceedings of the National Academy of Sciences.

[41]  Hector H. Huang,et al.  Force-dependent chemical kinetics of disulfide bond reduction observed with single-molecule techniques. , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[42]  B. Schmidt,et al.  Allosteric disulfide bonds. , 2006, Biochemistry.

[43]  B. Persson,et al.  Crack propagation in rubber-like materials , 2005 .

[44]  H. Clausen‐Schaumann,et al.  Mechanochemistry: the mechanical activation of covalent bonds. , 2005, Chemical reviews.

[45]  S. Bachrach,et al.  Competing elimination and substitution reactions of simple acyclic disulfides. , 2005, Organic & biomolecular chemistry.

[46]  Ali Fatemi,et al.  Factors that affect the fatigue life of rubber: A literature survey , 2004 .

[47]  P. Fernandes,et al.  Theoretical insights into the mechanism for thiol/disulfide exchange. , 2004, Chemistry.

[48]  S. Bachrach,et al.  Effect of Micro and Bulk Solvation on the Mechanism of Nucleophilic Substitution at Sulfur in Disulfides , 2003 .

[49]  P. Hogg,et al.  Disulfide bonds as switches for protein function. , 2003, Trends in biochemical sciences.

[50]  P. Li,et al.  Disulfide exchange in domain 2 of CD4 is required for entry of HIV-1 , 2002, Nature Immunology.

[51]  Frank Jensen,et al.  Steric Effects in SN2 Reactions. The Influence of Microsolvation , 2001 .

[52]  S. Patai,et al.  The Chemistry of sulphur-containing functional groups , 1993 .

[53]  J. J. Grabowski,et al.  Dimethyl disulfide: anion-molecule reactions in the gas phase at 300 K , 1989 .

[54]  T. Florence Degradation of protein disulphide bonds in dilute alkali. , 1980, The Biochemical journal.

[55]  A. Parker,et al.  The Scission Of The Sulfur-Sulfur Bond , 1959 .

[56]  R. Cecil,et al.  The sulfur chemistry of proteins. , 1959, Advances in protein chemistry.

[57]  J. Swan Mechanism of Alkaline Degradation of Cystine Residues in Proteins , 1957, Nature.

[58]  D. Tarbell,et al.  Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds. , 1951 .