A Fifty-Year Perspective on Chemistry in Water

Organic Reactions in Water: Principles, Strategies and Applications

Volumn , Issue , 2007, Pages 1-28

  Breslow, Ronald ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Cyclodextrin dimers; Diels alder reactions; Enzyme mimics; Hydrophobic binding; Quantitative antihydrophobic effects

Indexed keywords

EID: 84890642189     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470988817.ch1     Document Type: Chapter

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120. Zimmerman, S.C. and Breslow, R.,Asymmetric synthesis of amino acids by pyridoxamine enzymeanalogues utilizing general base-acid catalysis, J. Am. Chem. Soc., 1984, 106, 1490-1491.
121. Chmielewski, J. and Breslow, R., Increasing the racemase activity versus transaminase activity of a pyridoxal enzyme model by the attachment of a rigid base, Heterocycles, 1987, 25, 533.
122. Liu, L., Rozenman, M. and Breslow, R., 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 condensations, Bioorg. Med. Chem., 2002, 10, 3973- 3979.
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126. Liu, L. and Breslow, R., A potent polymer/pyridoxamine enzyme mimic, J. Am. Chem. Soc., 2002, 124, 4978-4979.
127. Zhou, W., Liu, L. and Breslow, R., Transamination by polymeric enzyme mimics, Helv. Chim. Acta, 2003, 86, 3560-3567.
128. Liu, L., Zhou,W., Chruma, J.J. and Breslow, R., Transamination reactions withmultiple turnovers catalyzed by hydrophobic pyridoxamine cofactors in the presence of polyethylenimine polymers, J. Am. Chem. Soc., 2004, 126, 8136-8137.
129. Liu, L. and Breslow, R., Polymeric and dendrimeric pyridoxal enzyme mimics, Bioorg. Med. Chem., 2004, 12, 3277-3287.
130. Liu, L. and Breslow, R., Dendrimeric pyridoxamine enzyme mimics, J. Am. Chem. Soc., 2003, 125, 12110- 12111.
131. Liu, L., Rozenman, M. and Breslow, R.,Hydrophobic effects on rates and substrate selectivities in polymeric transaminase mimics, J. Am. Chem. Soc., 2002, 124, 12660-12661.
132. Chruma, J.J., Liu, L., Zhou,W. and Breslow, R., Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics, Bioorg. Med. Chem., 2005, 13, 5873-5883.
133. Zhou,W., Yerkes, N., Chruma, J., Liu, L. and Breslow, R., Chiral polyamines from reduction of polypeptides: asymmetric pyridoxamine-mediated transaminations, Bioorg. Med. Chem. Lett., 2005, 15, 1351-1355.
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135. Koh, J.T., Delaude, L. and Breslow, R., Geometric control of a pyridoxal-catalyzed aldol condensation, J. Am. Chem. Soc., 1994, 116, 11234-11240.
136. Fasella, E., Dong, S.D. and Breslow, R., Reversal of optical induction in transamination by regioisomeric bifunctionalized cyclodextrins, Bioorg. Med. Chem., 1999, 7, 709-714.
137. Liu, L. andBreslow, R., Selective racemization in preference to transamination catalyzed by pyridoxal enzyme analogs, Tetrahedron Lett., 2001, 42, 2775-2777.
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139. Breslow, R., Zhang, X.,Xu, R.,Maletic, M. andMerger, R., Selective catalytic oxidation of substrates that bind to metalloporphyrin enzyme mimics carrying two or four cyclodextrin groups and related metallosalens, J. Am. Chem. Soc., 1996, 118, 11678-11679.
140. Breslow, R., Zhang, X. andHuang, Y., Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme, J. Am. Chem. Soc., 1997, 119, 4535-4536.
141. Breslow, R., Huang, Y., Zhang, X. and Yang, J., An artificial cytochrome P450 that hydroxylates unactivated carbons with regio- and stereoselectivity and useful catalytic turnovers, Proc. Natl. Acad. Sci. U.S.A., 1997, 94, 11156-11158.
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143. Yang, J. and Breslow, R., Selective hydroxylation of a steroid at C-9 by an artificial cytochrome P-450, Angew. Chem. Int. Ed., 2000, 39, 2692-2694.
144. Breslow, R., Yang, J. and Yan, J., Biomimetic hydroxylation of saturated carbons with artificial cytochrome P-450 enzymes-liberating chemistry fromthe tyranny of functional groups,Tetrahedron, 2002, 58, 653-659.
145. Breslow, R., Yan, J. and Belvedere, S., Catalytic hydroxylation of steroids by cytochrome P-450 mimics. Hydroxylation at C-9 with novel catalysts and steroid substrates, Tetrahedron Lett., 2002, 43, 363-365.
146. Yang, J., Gabriele, B., Belvedere, S., Huang, Y. and Breslow, R., Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes, J. Org. Chem., 2002, 67, 5057-5067.
147. Breslow, R. and Fang, Z., Hydroxylation of steroids with an artificial P-450 catalyst bearing synthetic cyclophanes as binding groups, Tetrahedron Lett., 2002, 43, 5197-5200.
148. Breslow, R. and Gellman, S.H., Tosylamidation of cyclohexane by a cytochrome P-450 model, J. Chem. Soc., Chem. Commun., 1982, 1400-1401.
149. Breslow, R. and Gellman, S.H., Intramolecular nitrene C-H insertions mediated by transition-metal complexes as nitrogen analogues of cytochrome P-450 reactions, J. Am. Chem. Soc., 1983, 105, 6728-6729.
150. Breslow, R.,Hydrophobic and antihydrophobic effects on organic reactions in aqueous solution, In: Cramer, C.J. and Truhlar, D.G. (Eds.), Structure and Reactivity in Aqueous Solution, American Chemical Society, Washington, DC, 1994, pp. 291-302.
151. Rideout, D. and Breslow, R., Hydrophobic acceleration of Diels-Alder reactions, J. Am. Chem. Soc., 1980, 102, 7816-7817.
152. Breslow, R. and Rizzo, C.J., Chaotropic salt effects in a hydrophobically accelerated Diels-Alder reaction, J. Am. Chem. Soc., 1991, 113, 4340-4341.
153. Breslow, R., Hydrophobic effects on simple organic reactions in water, Acc. Chem. Res., 1991, 24, 159-164.
154. Breslow, R.,Maitra,U. and Rideout,D., Selective Diels-Alder reactions in aqueous solutions and suspensions, Tetrahedron Lett., 1983, 24, 1901-1904.
155. Breslow, R. andMaitra,U.,Onthe origin of product selectivity in aqueous Diels-Alder reactions,Tetrahedron Lett., 1984, 25, 1239-1240.
156. Kool, E.T. and Breslow, R., Dichotomous salt effects in the hydrophobic acceleration of the benzoin condensation, J. Am. Chem. Soc., 1988, 110, 1596-1597.
157. Breslow, R. and Guo, T., Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers, Proc. Natl. Acad. Sci. U. S. A., 1990, 87, 167-169.
158. Breslow, R. and Guo, T., Diels-Alder reactions in nonaqueous polar solvents. Kinetic effects of chaotropic and antichaotropic agents and of beta-cyclodextrin, J. Am. Chem. Soc., 1990, 110, 5613-5617.
159. Biscoe, M. and Breslow, R.,Hydrophobically directed selective reduction of ketones, J. Am. Chem. Soc., 2003, 125, 12718-12719.
160. Biscoe, M.,Uyeda, C. and Breslow, R., Requirements for selective hydrophobic accelerations in the reduction of ketones, Org. Lett., 2004, 6, 4331-4334.
161. Uyeda, C., Biscoe, M., Le Plae, P. and Breslow, R., Hydrophobically-directed selective reduction of ketones using amine boranes, Tetrahedron Lett., 2005, 47, 127-130.
162. Biscoe, M. and Breslow, R., Oxaziridinium salts as hydrophobic epoxidation reagents: remarkable hydrophobically-directed selectivity in olefin epoxidation, J. Am. Chem. Soc., 2005, 127, 10812-10813.
163. Breslow, R., Determining the geometries of transition states by use of antihydrophobic additives in water, Acc. Chem. Res., 2004, 3, 471-478.
164. Breslow, R. and Halfon, S., Quantitative effects of antihydrophobic agents on binding constants and solubilities in water, Proc. Natl. Acad. Sci. U. S. A., 1992, 89, 6916-6918.
165. Breslow, R. and Connors, R.V., Quantitative antihydrophobic effects as probes for transition state structures. 1. Benzoin condensation and displacement reactions, J. Am. Chem. Soc., 1995, 117, 6601-6602.
166. Breslow, R. and Zhu, Z., Quantitative antihydrophobic effects as probes for transition state structures. 2. Diels-alder reactions, J. Am. Chem. Soc., 1995, 117, 9923-9924.
167. Breslow, R. and Connors, R., Antihydrophobic cosolvent effects detect two different geometries for an SN2 displacement and the change to a single-electron transfer mechanisms in related cases, J. Am. Chem. Soc., 1996, 118, 6323-6324.
168. Breslow, R., Connors, R. and Zhu, Z.,Mechanistic studies using antihydrophobic agents, Pure Appl. Chem., 1996, 68, 1527-1533.
169. Mayer, M.U. and Breslow, R., Antihydrophobic evidence for the single electron transfer mechanism of nucleophilic substitution, J. Am. Chem. Soc., 1998, 120, 9098-9099.
170. Breslow, R., Groves, K. and Mayer, M.U., The hydrophobic effect as a mechanistic tool, Pure Appl. Chem., 1998, 70, 1933-1938.
171. Breslow, R., Groves, K. and Mayer, M.U., Antihydrophobic cosolvent effects in organic displacement reactions, Org. Lett., 1999, 1, 117-120.
172. Breslow, R., Groves, K. andMayer, M.U., Antihydrophobic cosolvent effects for alkylation reactions in water solution, particularly oxygen versus carbon alkylations of phenoxide ions, J. Am. Chem. Soc., 2002, 124, 3622-3635.