Publications

Research Articles »
Chapters »
Patents »
Dissertations »

 

Article

Links
Ran, N.; Draths, K. M.; Frost, J. W. "Creation of a Shikimate Pathway Variant." J. Am. Chem. Soc. 2004, In press.
Guo, J.; Frost, J. W. "Synthesis of Aminoshikimic Acid." Org. Lett. 2004, 6, 1585.
Zha, W.; Shao, Z.; Frost, J. W.; Zhao, H. "Rational Pathway Engineering of Type I Fatty Acid Synthase Allows the Biosynthesis of Triacetic Acid Lactone from D-Glucose in Vivo." J. Am. Chem. Soc. 2004, 126, 4534
Chang, Y.-C; Almy, E. A.; Blamer, G. A.; Gray, I. A.; Frost, J. W.; Strasburg, G. M. "Antioxidant Activity of 3-Dehydroshikimic cid in Liposomes, Emulsions, and Bulk Oil." J. Agric. Food Chem. 2003, 51, 2753.
Chandran, S. C.; Yi, J.; Draths, K. M.; von Daeniken, R.; Weber, W.; Frost, J. W. "Phosphoenolpyruvate Availability and the Biosynthesis of Shikimic Acid." Biotechnol. Prog. 2003, 19, 808.
Yi, J.; Draths, K. M.; Li, K.; Frost, J. W. "Altered Glucose Transport and Shikimate Pathway Product Yields in E. coli." Biotechnol. Prog. 2003, 19, 1450.
Niu, W.; Molefe, M. N.; Frost, J. W. "Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol." J. Am. Chem. Soc. 2003, 125, 12998.
Guo, J.; Frost, J. W. "Biosynthesis of 1-Deoxy-1-imino-D-erythrose 4-Phosphate: A Defining Metabolite in the Aminoshikimate Pathway." J. Am. Chem. Soc. 2002, 124, 528.
Hansen, C.; Frost, J. W. "Deoxygenation of Polyhydroxybenzenes Derived from Glucose: An Alternative Strategy for the Benzene-Free Synthesis of Aromatic Chemicals." J. Am. Chem. Soc. 2002, 124, 5926.
Niu, W.; Draths, K. M.; Frost, J. W. "Benzene-Free Synthesis of Adipic Acid." Biotechnol. Prog. 2002, 18, 201.
Guo, J.; Frost, J. W. "Kanosamine Biosynthesis: A Likely Source of the Aminoshikimate Pathway's Nitrogen Atom." J. Am. Chem. Soc. 2002, 124, 10642.
Yi, J.; Li, K.; Draths, K. M.; Frost, J. W. "Modulation of Phosphoenolpyruvate Synthase Expression Increases Shikimate Pathway Product Yields in E. coli". Biotechnol. Prog. 2002, 18, 1141.
Chandran, S. C.; Frost, J. W. "Aromatic Inhibitors of Dehydroquinate Synthase: Synthesis, Evaluation and Implications for Gallic Acid Biosynthesis." Bioorg. Med. Chem. Lett. 2001, 11, 1493.  
Gibson, J. M.; Thomas, P. S.; Thomas, J. D.; Barker, J. L.; Chandran, S. S.; Harrup, Draths, K. M.; Frost, J. W. "Benzene-Free Synthesis of Phenol." Angew. Chemie, Int. Ed. 2001, 40, 1945.
Barker, J. L.; Frost, J. W. "Microbial Synthesis of p-Hydroxybenzoic Acid from Glucose." Biotechnol. Bioeng. 2001, 76, 376.
Knop, D. R.; Draths, K. M.; Chandran, S. S; Barker, J. L.; von Daeniken, R.;Weber, W.; Frost, J. W. "Hydroaromatic Equilibration During Biosynthesis of Shikimic Acid." J. Am. Chem. Soc. 2001, 123, 10173.
Ran, N.; Knop, D. R.; Draths, K. M.; Frost, J. W. "Benzene-Free Synthesis of Hydroquinone." J. Am. Chem. Soc. 2001, 123, 10927.
Kambourakis, S.; Frost, J. W. "Synthesis of Gallic Acid: Cu+2-Mediated Oxidation of 3-Dehydroshikimic Acid." J. Org. Chem. 2000, 65, 6904.
Kambourakis, S.; Draths, K. M.; Frost, J. W. "Synthesis of Gallic Acid and Pyrogallol from Glucose: Replacing Natural Product Isolation with Microbial Catalysis." J. Am. Chem. Soc. 2000, 122, 9042.
Li, K.; Mikola, M. R.; Draths, K. M.; Worden, R. M.; Frost, J. W. "Fed-Batch Fermentor Synthesis of 3-Dehydroshikimic Acid Using Recombinant Escherichia coli ." Biotechnol. Bioeng. 1999, 64, 61.
Draths, K. M.; Knop, D. R.; Frost, J. W. "Shikimic Acid and Quinic Acid: Replacing Isolation from Plant Sources with Recombinant Microbial Biocatalysis." J. Am. Chem. Soc. 1999, 121, 1603.
Hansen, C. A.; Dean, A. B.; Draths, K. M.; Frost, J. W. "Synthesis of 1,2,3,4-Tetrahydroxybenzenes from Glucose via myo-Inositol Intermediacy." J. Am. Chem. Soc. 1999, 121, 3799.
Tian, F.; Migaud, M. E.; Frost, J. W. "myo-Inositol 1-Phosphate Synthase: Does a Single Active-Site Amino Acid Catalyze Multiple Proton Transfers." J. Am. Chem. Soc. 1999, 121, 5795.
Li, K.; Frost, J. W. "Microbial Synthesis of 3-Dehydroshikimic Acid: A Comparative Analysis of D-Xylose, L-Arabinose, and D-Glucose Carbon Sources." Biotechnol. Prog. 1999, 15, 876.
Li, K.; Frost, J. W. "Succinic Acid as a Proform of Phosphoenolpyruvic Acid: Employing Glucose Adjuncts in Microbe-Catalyzed Synthesis." J. Am. Chem. Soc. 1999, 121, 9461.
Carpenter, E. P.; Hawkins, A. R.; Frost, J. W.; Brown, K. A. "Crystal Structure of Dehydroquinate Synthase: One Active Site Catalyzes Multiple Chemical Reactions." Nature 1998, 394, 299.  
Li, K.; Frost, J. W. "Synthesis of Vanillin from D-Glucose." J. Am. Chem. Soc. 1998, 120, 10545.
Montchamp, J.-L.; Frost, J. W. "Cyclohexenyl and Cyclohexylidene Inhibitors of 3-Dehydroquinate Synthase: Active Site Interactions Relevant to Enzyme Mechanism and Inhibitor Design." J. Am. Chem. Soc. 1997, 119, 7645.
Migaud, M. E.; Frost, J. W. "Elaboration of a General Strategy for Inhibition of MIP Synthase: Active Site Interactions of Analogues Possessing Oxidized Reaction Centers." J. Am. Chem. Soc. 1996, 118, 495.
Chee-Sanford, J. C.; Frost, J. W.; Fries, M. R.; Zhou, J.; Tiedje, J. M "Evidence for Acetyl Coenzyme A and Cinnamoyl Coenzyme A in the Anaerobic Toluene Mineralization Pathway in Azoracus tolulyticus Tol-4." Appl. Environ. Microbiol. 1996, 62, 964.  
Migaud, M. E.; Chee-Sanford, J. C.; Tiedje, J. M.; Frost, J. W. "Benzylfumaric, Benzylmaleic, and Z- and E-Phenylitaconic Acids: Synthesis, Characterization, and Correlation with a Metabolite Generated by Azoarcus tolulyticus Tol-4 during Anaerobic Toluene Degradation." Appl. Environ. Microbiol. 1996, 62, 974.  
Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. "2,3-Butane Bisacetal Protection of Vicinal Diequatorial Diols." J. Org. Chem. 1996, 61, 3897.
Snell, K. D.; Draths, K. M.; Frost, J. W. "Synthetic Modification of the Escherichia coli Chromosome: Enhancing the Biocatalytic Conversion of Glucose into Aromatic Chemicals." J. Am. Chem. Soc. 1996, 118, 5605.
Frost, J. W. "Renewable Feedstocks." Chem. Eng. 1996, May 16 (611), 32.  
Tian, F.; Montchamp, J.-L.; Frost, J. W. "Inhibitor Ionization as a Determinant of Binding to 3-Dehydroquinate Synthase." J. Org. Chem. 1996, 61, 7373.
Richman, J. E.; Chang, Y.-C.; Kambourakis, S.; Draths, K. M.; Almy, E.; Snell, K. D.; Strasburg, G. M.; Frost, J. W. "Reaction of 3-Dehydroshikimic Acid with Molecular Oxygen and Hydrogen Peroxide: Products, Mechanism, and Associated Antioxidant Activity." J. Am. Chem. Soc. 1996, 118, 11587.
Frost, J. W.; Draths, K. M. "Sweetening Chemical Manufacture." Chemistry in Britain 1995, 31, 206.  
Draths, K. M.; Frost, J. W. "Environmentally Compatible Synthesis of Catechol from D-Glucose." J. Am. Chem. Soc. 1995, 117, 2395.
Migaud, M. E.; Frost, J. W. "Inhibition of myo-Inositol-1-phosphate Synthase by a Reaction Coordinate Intermediate." J. Am. Chem. Soc. 1995, 117, 5154.
Montchamp, J.-L.; Tian, F.; Frost, J. W. "Double Arbuzov Reaction of in Situ Generated Bis(trimethylsiloxy)phosphine with Dielectrophiles: Methodology for the Synthesis of Cyclic Phosphinic Acids." J. Org. Chem. 1995, 60, 6076.
Frost, J. W.; Draths, K. M. "Biocatalytic Syntheses of Aromatics from D-Glucose: Renewable Microbial Sources of Aromatic Compounds." Ann. Rev. Microbiol. 1995, 49, 557.
Frost, J. W.; Lievense, J. "Prospects for Biocatalytic Synthesis of Aromatics in the 21st Century." New J. Chem. 1994, 18, 341.  
Draths, K. M.; Frost, J. W. "Environmentally Compatible Synthesis of Adipic Acid from D-Glucose." J. Am. Chem. Soc. 1994, 116, 399.
Dudley, M. W.; Frost, J. W. "Biocatalytic Desulfurization of Arylsulfonates." Bioorg. Med. Chem. 1994, 2, 681.  
Montchamp, J.-L.; Peng, J.; Frost, J. W. "Inversion of an Asymmetric Center in Carbocyclic Inhibitors of 3-Dehydroquinate Synthase: Examining and Exploiting the Mechanism for syn-Elimination During Substrate Turnover." J. Org. Chem. 1994, 59, 6999.
Montchamp, J.-L.; Frost, J. W. "Synthesis and Evaluation of 3-Dehydroquinate Synthase Transition State Analogues." J. Org. Chem. 1994, 59, 7596.
Montchamp, J.-L.; Piehler, L. T.; Tolbert, T. J.; Frost, J. W. "Designing Inhibitors of Dehydroquinate Synthase: Structural Simplicity Versus Inhibitory Potency." Bioorg. Med. Chem. Lett. 1993, 3, 1403.  
Dell, K. A.; Frost, J. W. "Identification and Removal of Impediments to Biocatalytic Synthesis of Aromatics from D-Glucose: Rate-Limiting Enzymes in the Common Pathway of Aromatic Amino Acid Biosynthesis." J. Am. Chem. Soc. 1993, 115, 11581.
Montchamp, J.-L.; Migaud, M. E.; Frost, J. W. "Phosphonomethylation of Cyclohexene Oxides." J. Org. Chem. 1993, 58, 7679.
Draths, K. M.; Pompliano, D. L.; Conley, D. L.; Frost, J. W.; Berry, A.; Disbrow, G.; Starversky, R.; Lievense, J. "Biocatalytic Synthesis of Aromatics from D-Glucose: The Role of Transketolase." J. Am. Chem. Soc. 1992, 114, 3956.
Montchamp, J.-L.; Piehler, L. T.; Frost, J. W. "Diastereoselection and In Vivo Inhibition of 3-Dehydroquinate Synthase." J. Am. Chem. Soc. 1992, 114, 4453.
Montchamp, Jean-Luc; Piehler, L. T.; Tolbert, T. J. "The Basis for Slowly Reversible Inhibition of Dehydroquinate Synthase: A Case of Mistaken Identity?" Bioorg. Med. Chem. Lett. 1992, 2, 1349.  
Draths, K. M.; Frost, J. W. "Combining Biocatalysis with Nineteenth Century Organic Chemistry: Conversion of D-Glucose into Quinoid Organics." J. Am. Chem. Soc. 1992, 114, 9725.
Avila, L. Z.; Bishop, P. A.; Frost, J. W. "Hydrocarbon and Phosphate Triester Formation During Homolytic Hydrolysis of Organophosphonium Ions: An Alternate Model for Organophosphonate Biodegradation." J. Am. Chem. Soc. 1991, 113, 2242.  
Piehler, L. T.; Montchamp, J.-L.; Frost, J. W.; Manly, C. J. "Predicting Inhibition of Dehydroquinate Synthase." Tetrahedron 1991, 47, 2423.  
Avila, L. Z.; Draths, K. M.; Frost, J. W. "Metabolites Associated with Organophosphonate C-P Bond Cleavage: Chemical Synthesis and Microbial Degradation of [32P]-Ethylphosphonic Acid." Bioorg. Med. Chem. Lett. 1991, 1, 51.  
Montchamp, J.-L.; Frost, J. W. "Irreversible Inhibition of 3-Dehydroquinate Synthase." J. Am. Chem. Soc. 1991, 113, 6296.  
Draths, K. M.; Frost, J. W. "Conversion of D-Glucose into Catechol: The Not-So-Common Pathway of Aromatic Biosynthesis." J. Am. Chem. Soc. 1991, 113, 9361.  
Draths, K. M.; Frost, J. W. "Synthesis Using Plasmid-Based Biocatalysis: Plasmid Assembly and 3-Deoxy-D-arabino-heptulosonate Production." J. Am. Chem. Soc. 1990, 112, 1657.  
Draths, K. M.; Frost, J. W. "Genomic Direction of Synthesis During Plasmid-Based Biocatalysis." J. Am. Chem. Soc. 1990, 112, 9630.  
Myrvold, S.; Reimer, L. M.; Pompliano, D. L.; Frost, J. W. "Chemical Inhibition of Dehydroquinate Synthase." J. Am. Chem. Soc. 1989, 111, 1861.  
Pompliano, D. L.; Reimer, L. M.; Myrvold, S.; Frost, J. W. "Probing Lethal Metabolic Perturbations in Plants with Chemical Inhibition of Dehydroquinate Synthase." J. Am. Chem. Soc. 1989, 111, 1866.  
Avila, L. Z.; Frost, J. W. "Phosphonium Ion Fragmentations Relevant to Organophosphonate Biodegradation." J. Am. Chem. Soc. 1989, 111, 8969.  
Avila, L. Z.; Frost, J. W. "Monomeric Metaphosphate Formation During Radical-Based Dephosphorylation." J. Am. Chem. Soc. 1988, 110, 7904.  
Frost, J. W.; Loo, S.; Cordeiro, M. L.; Li, D. "Radical-based Dephosphorylation and Organophosphonate Biodegradation." J. Am. Chem. Soc. 1987, 109, 2166.  
Mehdi, S.; Frost, J. W.; Knowles, J. R. "Dehydroquinate Synthase from Escherichia coli and its Substrate 3-Deoxy-D-arabino-heptulosonic Acid 7-Phosphate." Meth. Enzymol. 1987, 142, 306.  
Roach, M.; Ungar, L. W.; Zare, R. N.; Reimer, L. M.; Pompliano, D. L.; Frost, J. W. "Sensitive Fluorescence Detection of Alkylphosphonic Acids Using p-(9-Anthroyloxy) phenacyl Bromide." Analyt. Chem. 1987, 59, 1056.  
Avila, L. Z.; Loo, S. H.; Frost, J. W. "Chemical and Mutagenic Analysis of Aminomethylphosphonate Biodegradation." J. Am. Chem. Soc. 1987, 109, 6758.  
Loo, S. H.; Peters, N. K.; Frost, J. W. "Genetic Characterization of an Escherichia coli Mutant Deficient in Organophosphonate Biodegradation." Biochem. Biophys. Res. Comm. 1987, 148, 148.  
Cordeiro, M. L.; Pompliano, D. L.; Frost, J. W. "Degradation and Detoxification of Organophosphonates: Cleavage of the Carbon to Phosphorus Bond." J. Am. Chem. Soc. 1986, 108, 332.  
Reimer, L. M.; Conley, D. L.; Pompliano, D. L.; Frost, J. W. "Construction of an Enzyme-Targeted Organophosphonate Using Immobilized Enzyme and Whole Cell Synthesis." J. Am. Chem. Soc. 1986, 108, 8010.  
Peters, N. K.; Frost, J. W.; Long, S. R. "A plant flavone, luteolin, induces expression of Rhizobium meliotii nodulation genes." Science 1986, 223, 977.  
Frost, J. W.; Bender, J. L.; Kadonaga, J. T.; Knowles, J. R. "Dehydroquinate Synthase: Purification, Cloning, and the Construction of E. coli Overproducers of the Enzyme." Biochemistry 1984, 23, 4470.  
Frost, J. W.; Knowles, J. R. "3-Deoxy-D-arabino-heptulosonic acid 7-phosphate: Chemical Synthesis and Isolation from Escherichia coli Auxotrophs." Biochemistry 1984, 23, 4465.  
Frost, J. W. "5-Thio-D-glucose: How Do Enzymes Work?" Aldrichim. Acta 1983, 16, 3.  
Frost, J. W.; Rastetter, W. H. "Flavoprotein Monooxygenases: A Chemical Model." J. Am. Chem. Soc. 1981, 103, 5242.  
Frost, J. W.; Rastetter, W. H. "Biomimetic 8-alpha Functionalization of Riboflavin." J. Am. Chem. Soc. 1980, 102, 7157.  
Feuer, H.; Blecker, L. R.; Jans, Jr., R. W.; Frost, J. W. "Alkyl Nitrate Nitration of Active Methylene Compounds." J. Heterocyclic Chem. 1979, 16, 481.  
Rastetter, W. H.; Gadek, T. R.; Tane, J. P.; Frost, J. W. "Oxidations and Oxygen Transfers Effected by a Flavin N(5)-Oxide. A Model for Flavin-Dependent Monooxygenases." J. Am. Chem. Soc. 1979, 101, 2228.  
Rastetter, W. H.; Adams, J.; Frost, J. W.; Nummy, L. J.; Frommer, J. E.; Roberts, K. B. "On the Involvement of Lipoic Acid in Alpha-Keto Acid Dehydrogenase Complexes." J. Am. Chem. Soc. 1979, 101, 2752.  
Rastetter, W. H.; Frost, J. W. "Oxaziridines and Oxygen Transfer." Tetrahedron Lett. 1979, 3353.