Selected Publications

Edward R. Thornton

Neelamkavil, S.; Arison, B.; Birzin, E.; Feng, J.-J.; Chen, K.-H.; Lin, A.; Cheng, F.-C.; Taylor, L.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. J. Med. Chem. 2005, 48, 4025-4030. "Replacement of Phe6, Phe7, and Phe11 of D-Trp8-Somatostatin-14 with L-Pyrazinylalanine. Predicted and Observed Effects on Binding Affinities at hSST2 and hSST4. An Unexpected Effect of the Chirality of Trp8 on NMR Spectra in Methanol."

Angeles, A. R.; Neagu, I.; Birzin, E. T.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. Org. Lett. 2005, 7, 1121-1124. "Synthesis and Binding Affinities of Novel SRIF-Mimicking beta-D-Glucosides Satisfying the Requirement for a pi-Cloud at C1."

Neelamkavil, S.; Mowery, B.P.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. J. Pept. Res. 2005, 65, 139-142. "A Practical Synthesis of Nalpha-Fmoc-L-pyrazinylalanine via Schöllkopf’s Chiral Auxiliary."

Turowski, M.; Yamakawa, N.; Meller, J.; Kimata, K.; Ikegami, T.; Hosoya, K.; Tanaka, N.; Thornton, E. R. J. Am. Chem. Soc. 2003, 125, 13836-13849. "Deuterium Isotope Effects on Hydrophobic Interactions: The Importance of Dispersion Interactions in the Hydrophobic Phase."

Prasad, V.; Birzin, E. T.; McVaugh, C. T.; van Rijn, R. D.; Rohrer, S. P.; Chicchi, G.; Underwood, D. J.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. J. Med. Chem. 2003, 46, 1858-1869. "Effects of Heterocyclic Aromatic Substituents on Binding Affinities at Two Distinct Sites of Somatostatin Receptors. Correlation with the Electrostatic Potential of Substituents."

Przeslawski, R. M.; Newman, S.; Thornton, E. R.; Joullie, M. M. Syn. Commun. 1995, 25, 2975-2980. "A short, Affordable, One-Pot synthesis of a Camphor-Derived Amino Alcohol."

Choudhury, A.; Thornton, E. R. Tetrahedron Lett. 1993, 34, 2221-2224, "alpha´-Benzoyloxy and alpha´-Methoxymethoxy Lithium Enolates Giving Opposite Diastereofacial Selectivities in Aldol Reactions. Use of (Probable) Extended Chelation for Reversal of Stereoselectivities."

Das, G.; Thornton, E. R. J. Am. Chem. Soc. 1993, 115, 1302-1312, "Aldol Additions of Pinacolone Lithium Enolate with Ketones: Reactivities Governed Predominantly by Field Effects."

Reddy, D. R.; Thornton, E. R., J. Chem. Soc., Chem. Commun. 1992, 172-173, "A Very Mild, Catalytic and Versatile Procedure for alpha-Oxidation of Ketone Silyl Enol Ethers Using (salen)Manganese(III) Complexes; A New, Chiral Complex Giving Asymmetric Induction. A Possible Model for Selective Biochemical Oxidative Reactions Through Enol Formation."

Siegel, C.; Thornton, E. R., Tetrahedron: Asymmetry 1991, 2, 1413-1428, "Diels-Alder Reactions with Dienes Bearing a Remote Stereogenic Center. Conformational Model for Diastereofacial Selectivity." [invited paper]

Tripathy, R.; Carroll, P. J.; Thornton, E. R., J. Am. Chem. Soc. 1991, 113, 7630-7640, "Diene-Dienophile Hydrogen-Bonding Control of Diels-Alder Reactions with Dienes Bearing a Remote Stereogenic Center. Amplification of the Receptor Nature of Dienes by Conformational Tuning Leading to High Diastereofacial Discrimination."

Prapansiri, V.; Thornton, E. R., Tetrahedron Lett. 1991, 32, 3147-3150, "Asymmetric Diels-Alder Reactions. Inverse Electron Demand Reactions of Esters of 3-Hydroxypyran-2-one with Vinyl Ethers: Use of High Pressure to Avoid Decarboxylation of Adducts."

Nerz-Stormes, M.; Thornton, E. R., J. Org. Chem. 1991, 56, 2489-2498, "Asymmetric Aldol Reactions. Use of the Titanium Enolate of a Chiral N-Acyloxazolidinone to Reverse Diastereofacial Selectivities."

Bonner, M. P.; Thornton, E. R., J. Am. Chem. Soc. 1991, 113, 1299-1308, "Asymmetric Aldol Reactions. A New Camphor-Derived Chiral Auxiliary Giving Highly Stereoselective Aldol Reactions of Both Lithium and Titanium(IV) Enolates."

Panyachotipun, C.; Thornton, E. R., Tetrahedron Lett. 1990, 31, 6001-6004, "Steric Influence of Silyl Groups in Titanium- and Lithium-Mediated Aldol Condensations."

Shirodkar, S.; Nerz-Stormes, M.; Thornton, E. R., Tetrahedron Lett. 1990, 31, 4699-4702, "Asymmetric Aldol Reactions. Mechanism of Solvent Effect on Stereoselectivity Is Specific, Stoichiometric Binding of Tetrahydrofuran to a Chiral Titanium Enolate."

Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722-5728, "Asymmetric Aldol Reactions. A Titanium Enolate Giving Very High Diastereofacial Selectivities."

Nerz-Stormes, M.; Thornton, E. R. J. Am. Chem. Soc. 1984, 106, 5240-5246, "Carbon-13 Spin-Lattice Relaxation Studies of GD1a Micelles. Limited Segmental Motion of Head Group Saccharide Units."

Wydila, J.; Thornton, E. R. J. Org. Chem. 1984, 49, 244-249, "Synthesis and Photochemical Studies of a Diazomalonyl-Containing Galactocerebroside Analogue. A Glycolipid Photolabeling Reagent."

Keilbaugh, S. A.; Thornton, E. R. Biochemistry 1983, 22, 5063-5068, "Photolysis of Cholesteryl Diazoacetate in Small Unilamellar Vesicles."

Keilbaugh, S. A.; Thornton, E. R. J. Am. Chem. Soc. 1983, 105, 3283-3286, "Synthesis and Photoreactivity of Cholesteryl Diazoacetate: A Novel Photolabeling Reagent."

Thornton, E. K.; Thornton, E. R. In Transition States of Biochemical Processes; Gandour, R. D.; Schowen, R. L., Eds.; Plenum Press: New York, 1978, Chapter 1, pp. 3-76, "Scope and Limitations of the Concept of the Transition State."

Winey, D. A.; Thornton, E. R. J. Am. Chem. Soc. 1975, 97, 3102-3108, "Elimination Mechanisms. Deuteroxide/Hydroxide Isotope Effects as a Measure of Proton Transfer in the Transition States for E2 Elimination of 2-(p-Trimethylammoniophenyl)ethyl 'Onium Ions and Halides. Mapping of the Reaction-Coordinate Motion."

Choi, M.-u.; Thornton, E. R. J. Am. Chem. Soc. 1974, 96, 1428-1436, "A Kinetic Study of the Hydrolysis of Substituted N-Benzoylimidazoles and N-Benzoyl--methylimidazolium Ions in Light and Heavy Water. Hydrogen Bridging without Rate-Determining Proton Transfer as a Mechanism of General Base Catalyzed Hydrolysis and a Model for Enzymic Charge-Relay."

Taagepera, M.; Thornton, E. R. J. Am. Chem. Soc. 1972, 94, 1168-1177, "Secondary Deuterium Isotope Effects. The Transition State in the Reverse Diels-Alder Reaction of 9,10-Dihydro-9,10-ethanoanthracene. A Potentially General Method for Experimentally Determining Transition-State Symmetry and Distinguishing Concerted from Stepwise Mechanisms."

Thornton, E. K.; Thornton, E. R. In Isotope Effects in Chemical Reactions; Collins, C. J.; Bowman, N. S., Eds.; Van Nostrand Reinhold: New York, 1970, Chapter 4, pp. 213-285, "Origin and Interpretation of Isotope Effects."

Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 2915-2927, "A Simple Theory for Predicting the Effects of Substituent Changes on Transition-State Geometry."

All E. R. Thornton Publications



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