RONALD C BRESLOW

Summary

Affiliation: Columbia University
Country: USA

Publications

  1. ncbi request reprint Antihydrophobic cosolvent effects in organic displacement reactions
    R Breslow
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    Org Lett 1:117-20. 1999
  2. doi request reprint Catalysis of glyceraldehyde synthesis by primary or secondary amino acids under prebiotic conditions as a function of pH
    Ronald Breslow
    Columbia University, New York City, USA
    Orig Life Evol Biosph 43:323-9. 2013
  3. pmc Transketolase reaction under credible prebiotic conditions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 110:4184-7. 2013
  4. pmc L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 107:5723-5. 2010
  5. doi request reprint Imitating prebiotic homochirality on Earth
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Orig Life Evol Biosph 40:11-26. 2010
  6. pmc On the origin of terrestrial homochirality for nucleosides and amino acids
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 106:9144-6. 2009
  7. ncbi request reprint Water exclusion and enantioselectivity in catalysis
    Ronald Breslow
    Department of Chemistry, Columbia University New York, NY 10027, USA
    Chembiochem 7:1491-6. 2006
  8. pmc Amplification of enantiomeric concentrations under credible prebiotic conditions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 103:12979-80. 2006
  9. ncbi request reprint Oxaziridinium salts as hydrophobic epoxidation reagents: remarkable hydrophobically-directed selectivity in olefin epoxidation
    Mark R Biscoe
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    J Am Chem Soc 127:10812-3. 2005
  10. ncbi request reprint Antihydrophobic cosolvent effects for alkylation reactions in water solution, particularly oxygen versus carbon alkylations of phenoxide ions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 124:3622-35. 2002

Research Grants

  1. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2006
  2. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2005
  3. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2004
  4. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2003
  5. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2002
  6. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2001
  7. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2000
  8. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 1999
  9. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2007

Collaborators

  • Mindy Levine
  • Richard Friesner
  • Bartolo Gabriele
  • David Wilson
  • Ying Huang
  • Lei Liu
  • Wenjun Zhou
  • Zhenglai Fang
  • Mark R Biscoe
  • Rachid Skouta
  • Sujun Wei
  • Jason J Chruma
  • Severin T Schneebeli
  • Huanyu Zhao
  • Subhajit Bandyopadhyay
  • Paul A Marks
  • Jerry Yang
  • Mary Rozenman
  • Jianing Wang
  • Scott Venhuizen
  • Michelle Lynn Hall
  • Frank W Foss
  • Nancy Yerkes
  • Jason Chruma
  • Christopher Uyeda
  • Sandro Belvedere

Detail Information

Publications32

  1. ncbi request reprint Antihydrophobic cosolvent effects in organic displacement reactions
    R Breslow
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    Org Lett 1:117-20. 1999
    ..The effects have been sorted out for some displacement reactions, revealing the geometry of an interesting branching reaction whose two paths show different antihydrophobic effects...
  2. doi request reprint Catalysis of glyceraldehyde synthesis by primary or secondary amino acids under prebiotic conditions as a function of pH
    Ronald Breslow
    Columbia University, New York City, USA
    Orig Life Evol Biosph 43:323-9. 2013
    ..Detailed mechanistic proposals make these preferences understandable. The relevance of these findings to the origin of D sugars on prebiotic Earth is described. ..
  3. pmc Transketolase reaction under credible prebiotic conditions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 110:4184-7. 2013
    ....
  4. pmc L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 107:5723-5. 2010
    ..The D/L glyceraldehyde ratio in water solution is amplified to 92/8 using simple selective solubilities of the D and the DL forms. This D center would then be carried into the prebiotic syntheses of larger sugars...
  5. doi request reprint Imitating prebiotic homochirality on Earth
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Orig Life Evol Biosph 40:11-26. 2010
    ..Thus when credible examples are produced where small enantioexcesses of D-ribose are created under credible prebiotic conditions, the prerequisites for the RNA world will have been exemplified...
  6. pmc On the origin of terrestrial homochirality for nucleosides and amino acids
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 106:9144-6. 2009
    ..Guanosine crystallizes as a conglomerate and does not amplify in this way. However, under prebiotic conditions it could have been formed from homochiral D ribose from the hydrolysis of amplified adenosine or cytidine...
  7. ncbi request reprint Water exclusion and enantioselectivity in catalysis
    Ronald Breslow
    Department of Chemistry, Columbia University New York, NY 10027, USA
    Chembiochem 7:1491-6. 2006
  8. pmc Amplification of enantiomeric concentrations under credible prebiotic conditions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Proc Natl Acad Sci U S A 103:12979-80. 2006
    ..Such a process on the prebiotic earth could lead to a mechanism by which meteoritic chiral alpha-alkyl amino acids could form solutions with high ee values that were needed for the beginning of biology...
  9. ncbi request reprint Oxaziridinium salts as hydrophobic epoxidation reagents: remarkable hydrophobically-directed selectivity in olefin epoxidation
    Mark R Biscoe
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    J Am Chem Soc 127:10812-3. 2005
    ..Furthermore, the oxaziridinium ions could be generated with oxone from catalytic amounts of the corresponding iminium salts. These substrate selectivities should also carry over to positional selectivities in polyenes...
  10. ncbi request reprint Antihydrophobic cosolvent effects for alkylation reactions in water solution, particularly oxygen versus carbon alkylations of phenoxide ions
    Ronald Breslow
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 124:3622-35. 2002
    ..The mechanisms and explanations for competing oxygen and carbon alkylations differ from previous proposals by others...
  11. ncbi request reprint Biomimetic selectivity
    R Breslow
    Department of Chemistry, Columbia University, Chandler Laboratory, New York, New York 10027, USA
    Chem Rec 1:3-11. 2001
    ..Recent work uses a mimic of the enzyme class cytochrome P-450 to achieve the selective hydroxylations of steroids with complete domination by the geometry of the catalyst-substrate complex...
  12. ncbi request reprint Polymeric and dendrimeric pyridoxal enzyme mimics
    Lei Liu
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Bioorg Med Chem 12:3277-87. 2004
    ....
  13. doi request reprint Dendrimers in solution can have their remote catalytic groups folded back into the core: enantioselective transaminations by dendritic enzyme mimics-II
    Sujun Wei
    Columbia University, Department of Chemistry, 3000 Broadway, New York, NY 10027, USA
    Bioorg Med Chem Lett 19:5543-6. 2009
    ..Transamination to afford natural isomers of phenylalanine and alanine induced enantioselectivity by the peripheral chiral caps, supporting a computer model that indicates folding of dendrimer chains back into the core...
  14. ncbi request reprint Enantioselective synthesis and enantiomeric amplification of amino acids under prebiotic conditions
    Mindy Levine
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Org Lett 10:2433-6. 2008
    ..This asymmetry can be amplified to nearly homochiral levels, thus providing the necessary prerequisite for life to start on this planet and elsewhere in the universe...
  15. ncbi request reprint Chiral polyamines from reduction of polypeptides: asymmetric pyridoxamine-mediated transaminations
    Wenjun Zhou
    Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA
    Bioorg Med Chem Lett 15:1351-5. 2005
    ..These compounds transaminate alpha-ketoacids with moderate to good enantioselectivity, while their peptidyl counterparts show almost no chiral induction...
  16. ncbi request reprint Catalytic oxidations of steroid substrates by artificial cytochrome p-450 enzymes
    Jerry Yang
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Org Chem 67:5057-67. 2002
    ..Selective hydroxylations of steroid carbon 9 positions are of particular practical interest...
  17. ncbi request reprint Dendrimeric pyridoxamine enzyme mimics
    Lei Liu
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 125:12110-1. 2003
    ..The new catalysts showed both general acid/base catalysis by their amino groups and hydrophobic binding of the phenylpyruvate substrate...
  18. ncbi request reprint Stereoselectivity in reactions of amino acids catalyzed by pyridoxal derivatives carrying rigidly-attached chirally-mounted basic groups--transamination, racemization, decarboxylation, retro-aldol reaction, and aldol condensation
    Lei Liu
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Bioorg Med Chem 10:3973-9. 2002
    ..The observed stereoselectivities were all consistent with prediction...
  19. ncbi request reprint Hydrophobic effects on rates and substrate selectivities in polymeric transaminase mimics
    Lei Liu
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 124:12660-1. 2002
    ..The result is that the amination of indolepyruvic acid to produce tryptophan is accelerated by 240000-fold...
  20. pmc Metal coordination-directed hydroxylation of steroids with a novel artificial P-450 catalyst
    Zhenglai Fang
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    Org Lett 8:251-4. 2006
    ....
  21. ncbi request reprint Determining the geometries of transition States by use of antihydrophobic additives in water
    Ronald Breslow
    Department of Chemistry, Columbia University New York, New York 10027, USA
    Acc Chem Res 37:471-8. 2004
    ..Methods were devised to sort out the effect of the cosolvents on solvation of hydrophobic surfaces and the effect on solvation of polar groups. The result is a set of geometries for these reactions that is consistent with theory...
  22. ncbi request reprint Transamination reactions with multiple turnovers catalyzed by hydrophobic pyridoxamine cofactors in the presence of polyethylenimine polymers
    Lei Liu
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    J Am Chem Soc 126:8136-7. 2004
    ..Turnover catalysis was achieved by sacrificial oxidative decarboxylation of C-substituted amino acids, which reconverted the pyridoxals to pyridoxamines...
  23. pmc Isotactic polyethylenimines induce formation of L-amino acids in transamination
    Subhajit Bandyopadhyay
    Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA
    Org Lett 9:1009-12. 2007
    ..However, the racemization did not occur when the coenzyme was covalently attached to the polymer. [reaction: see text]..
  24. ncbi request reprint Helical templating of oligopeptides by cyclodextrin dimers
    David Wilson
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Bioorg Med Chem 11:2649-53. 2003
    ..Our studies suggest that receptors of this type may be useful in molecular recognition of hydrophobic, already alpha-helical peptides in aqueous solution...
  25. pmc High rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics
    Rachid Skouta
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 131:15604-5. 2009
    ..The properties of various polyvinylimidazoles were compared, including those prepared with the RAFT modification of the polymerization process...
  26. pmc Quantitative DFT modeling of the enantiomeric excess for dioxirane-catalyzed epoxidations
    Severin T Schneebeli
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 131:3965-73. 2009
    ..Our work suggests the possibility of using computational methods not simply to explain organic phenomena, but also to predict them quantitatively...
  27. ncbi request reprint A potent polymer/pyridoxamine enzyme mimic
    Lei Liu
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 124:4978-9. 2002
    ..The acceleration by polymer is a strong function of the length of the alkyl chains that are appended. The polymer furnishes acid and base groups to catalyze the proton transfers that are involved in transamination...
  28. pmc Artificial enzymes with thiazolium and imidazolium coenzyme mimics
    Huanyu Zhao
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    J Am Chem Soc 130:12590-1. 2008
    ..Polycationic enzyme mimics provide not only a hydrophobic binding domain for coenzyme and substrate, but also electrostatic stabilization of anionic species that arise along the reaction pathway of the benzoin condensation...
  29. ncbi request reprint Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug
    Paul A Marks
    Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10021, USA
    Nat Biotechnol 25:84-90. 2007
    ..A new drug application was approved by the US Food and Drug Administration for vorinostat for treatment of cutaneous T-cell lymphoma. More potent analogs of SAHA have shown unacceptable toxicity...
  30. ncbi request reprint Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics
    Jason J Chruma
    Columbia University, Department of Chemistry, 3000 Broadway, New York, NY 10027, USA
    Bioorg Med Chem 13:5873-83. 2005
    ..The effects of hydrophobic and electronic factors in the 2,2-disubstituted sacrificial amine source and the pyridoxamine catalyst on turnover frequency and turnover number are explored...
  31. ncbi request reprint Requirements for selective hydrophobic acceleration in the reduction of ketones
    Mark R Biscoe
    Department of Chemistry, Columbia University, New York, New York 10027, USA
    Org Lett 6:4331-4. 2004
    ..Some derivatives of naturally occurring steroid diones have also been employed as substrates to probe the mechanism and utility of these hydrophobically accelerated selective reductions further...
  32. ncbi request reprint A thiolate ligand on a cytochrome P-450 mimic permits the use of simple environmentally benign oxidants for biomimetic steroid hydroxylation in water
    Zhenglai Fang
    Department of Chemistry, Columbia University, New York, NY 10027, USA
    Bioorg Med Chem Lett 15:5463-6. 2005
    ..Thiol ligands were then added to the catalyst, both covalently attached and hydrophobically bound, and with these ligands hydrogen peroxide was now an effective oxidant...

Research Grants16

  1. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2006
    ..Here too the health relevance is the development of novel synthetic methods that could be useful in the manufacture of medicinal compounds. In addition, both parts of the project will help us understand natural enzymes. ..
  2. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2005
    ..Here too the health relevance is the development of novel synthetic methods that could be useful in the manufacture of medicinal compounds. In addition, both parts of the project will help us understand natural enzymes. ..
  3. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2004
    ..Here too the health relevance is the development of novel synthetic methods that could be useful in the manufacture of medicinal compounds. In addition, both parts of the project will help us understand natural enzymes. ..
  4. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2003
    ..For this to be possible, it is important that they function in water solution, as they are designed to do. ..
  5. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2002
    ..For this to be possible, it is important that they function in water solution, as they are designed to do. ..
  6. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2001
    ..For this to be possible, it is important that they function in water solution, as they are designed to do. ..
  7. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2000
    ..For this to be possible, it is important that they function in water solution, as they are designed to do. ..
  8. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 1999
    ..They may prove to be useful medicinals in their own right, replacing or augmenting catalysis by natural enzymes. For this to be possible, it is important that they function in water solution, as they are designed to do. ..
  9. BIOCHEMICAL MODEL REACTIONS
    Ronald Breslow; Fiscal Year: 2007
    ..Here too the health relevance is the development of novel synthetic methods that could be useful in the manufacture of medicinal compounds. In addition, both parts of the project will help us understand natural enzymes. ..