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John Wesley Frost

BIOGRAPHICAL INFORMATION
Current Position: Professor, Department of Chemistry
Phone Number: 517-355-9715 ext 115
Facsimile: 517-432-3873
Internet: frostjw@chemistry.msu.edu
Born: December 9, 1955

EDUCATION AND PROFESSIONAL EXPERIENCE
1973-1977 Undergraduate Studies, Purdue University
1977

Senior Research, Purdue University "Alkyl Nitrate Nitration of Active Methylene Compounds"
H. Feuer, Director

1977 B.S. in Chemistry, Purdue University
1977-1981 Graduate Studies, Massachusetts Institute of Technology "Elucidation of the Quinone Methide Tautomer of Riboflavin and Generation of a Flavin Nitroxyl Radical"
W. H. Rastetter, Director
1981-1983

Postdoctoral Studies, Harvard University
"A Study of the Mechanism of Action of DHQ Synthase"
J. R. Knowles, Director

1983-1988 Assistant Professor, Stanford University
Department of Chemistry
1989-1993 Associate Professor, Purdue University
Department of Chemistry
1994- Professor, Michigan State University
Department of Chemistry
2000- Director, Michigan State University
Center for Plant Products and Technologies
2001- Member, Bioorganic and Natural Products Study Section
National Institutes of Health

PRIVATE SECTOR EXPERIENCE

1988-1989 Consultant, Lilly Research Laboratories
1990-1992 Consultant, DowElanco
1991-1993 Consultant, Genencor International
1993-1995 Consultant, Viridis Inc.
1994-1995 Consultant, Archer-Daniels-Midland
1995-1997 President, Viridis Inc.
1998-2000 Member, Biotechnology Advisory Board, Dow Chemical
1999- Consultant, Givaudan Roure
2000-2002 Member, Scientific Advisory Board, Maxygen and Codexis

HONORS AND AWARDS
1977 Phi Kappa Phi
1977 Phi Beta Kappa
1977 Graduate with Distinction, Purdue University
1981-1983 National Institute of Health Postdoctoral Fellow
1985 Rohm and Haas Summer Faculty Fellowship
1985-1988 Searle Scholar
1987-1989 Sloan Fellow
1987-1992 Camille and Henry Dreyfus Teacher-Scholar Award
1991 Cyanamid Faculty Award
1998 The Presidential Green Chemistry Challenge Award
2001 Distinguished Faculty Award
College of Natural Science, Michigan State University


PUBLICATIONS
1. "Alkyl Nitrate Nitration of Active Methylene Compounds"
Feuer, H.; Blecker, L. R.; Jans, Jr., R. W.; Frost, J. W. J. Heterocyclic Chem. 1979, 16, 481.

2. "Oxidations and Oxygen Transfers Effected by a Flavin N(5)-Oxide. A Model for Flavin-Dependent Monooxygenases"
Rastetter, W. H.; Gadek, T. R.; Tane, J. P.; Frost, J. W. J. Am. Chem. Soc. 1979, 101, 2228.

3. "On the Involvement of Lipoic Acid in Alpha-Keto Acid Dehydrogenase Complexes"
Rastetter, W. H.; Adams, J.; Frost, J. W.; Nummy, L. J.; Frommer, J. E.; Roberts, K. B. J. Am. Chem. Soc. 1979, 101, 2752.

4. "Oxaziridines and Oxygen Transfer"
Rastetter, W. H.; Frost, J. W. Tetrahedron Lett. 1979, 3353.

5. "Biomimetic 8-alpha Functionalization of Riboflavin"
Frost, J. W.; Rastetter, W. H. J. Am. Chem. Soc. 1980, 102, 7157.

6. "Flavoprotein Monooxygenases: A Chemical Model"
Frost, J. W.; Rastetter, W. H. J. Am. Chem. Soc. 1981, 103, 5242.

7. "5-Thio-D-glucose: How Do Enzymes Work?"
Frost, J. W. Aldrichim. Acta 1983, 16, 3.

8. "Dehydroquinate Synthase: Purification, Cloning, and the Construction of E. coli Overproducers of the Enzyme"
Frost, J. W.; Bender, J. L.; Kadonaga, J. T.; Knowles, J. R. Biochemistry 1984, 23, 4470.

9. "3-Deoxy-D-arabino-heptulosonic acid 7-phosphate: Chemical Synthesis and Isolation from Escherichia coli Auxotrophs"
Frost, J. W.; Knowles, J. R. Biochemistry 1984, 23, 4465.

10. "Degradation and Detoxification of Organophosphonates: Cleavage of the Carbon to Phosphorus Bond"
Cordeiro, M. L.; Pompliano, D. L.; Frost, J. W. J. Am. Chem. Soc. 1986, 108, 332.

11. "Construction of an Enzyme-Targeted Organophosphonate Using Immobilized Enzyme and Whole Cell Synthesis"
Reimer, L. M.; Conley, D. L.; Pompliano, D. L.; Frost, J. W. J. Am. Chem. Soc. 1986, 108, 8010.

12. "A plant flavone, luteolin, induces expression of Rhizobium melioti nodulation genes"
Peters, N. K.; Frost, J. W.; Long, S. R. Science 1986, 223, 977.

13. "Radical-based Dephosphorylation and Organophosphonate Biodegradation"
Frost, J. W.; Loo, S.; Cordeiro, M. L.; Li, D. J. Am. Chem. Soc. 1987, 109, 2166.

14. "Dehydroquinate Synthase from Escherichia coli and its Substrate 3-Deoxy-D-arabino-heptulosonic Acid 7-Phosphate"
Mehdi, S.; Frost, J. W.; Knowles, J. R. Meth. Enzymol. 1987, 142, 306.

15. "Sensitive Fluorescence Detection of Alkylphosphonic Acids Using p-(9-Anthroyloxy) phenacyl Bromide"
Roach, M.; Ungar, L. W.; Zare, R. N.; Reimer, L. M.; Pompliano, D. L.; Frost, J. W. Anal. Chem. 1987, 59, 1056.

16. "Chemical and Mutagenic Analysis of Aminomethylphosphonate Biodegradation"
Avila, L. Z.; Loo, S. H.; Frost, J. W. J. Am. Chem. Soc. 1987, 109, 6758.

17. "Genetic Characterization of an Escherichia coli Mutant Deficient in Organophosphonate Biodegradation"
Loo, S. H.; Peters, N. K.; Frost, J. W. Biochem. Biophys. Res. Comm. 1987, 148, 148.

18. "Organophosphonate Biodegradation: Determining the Fate of Phosphorus"
Frost, J. W.; Zare, R. N. In Proceedings of the 1987 Army Chemical Research, Development and Engineering Center Scientific Conference on Chemical Defense Research; Rausa, M. D. Ed.; 1987; Vol I, p 133.

19. "Monomeric Metaphosphate Formation During Radical-Based Dephosphorylation"
Avila, L. Z.; Frost, J. W. J. Am. Chem. Soc. 1988, 110, 7904.

20. "Chemistry and the Environment 1988, a National Science Foundation Workshop Report"
Frost, J. W.; Golden, D. M. National Science Foundation: Washington, 1988.

21. "Chemical Inhibition of Dehydroquinate Synthase"
Myrvold, S.; Reimer, L. M.; Pompliano, D. L.; Frost, J. W. J. Am. Chem. Soc. 1989, 111, 1861.

22. "Probing Lethal Metabolic Perturbations in Plants with Chemical Inhibition of Dehydroquinate Synthase"
Pompliano, D. L.; Reimer, L. M.; Myrvold, S.; Frost, J. W. J. Am. Chem. Soc. 1989, 111, 1866.

23. "Phosphonium Ion Fragmentations Relevant to Organophosphonate Biodegradation"
Avila, L. Z.; Frost, J. W. J. Am. Chem. Soc. 1989, 111, 8969.

24. "Simple Carbohydrates as Starting Materials in Organic Synthesis: A Comparison of Strategies"
Frost, J. W.; Reimer, L. M.; Draths, K. M.; Pompliano, D. L.; Conley, D. L. In Biocatalysis; Abramowicz, D. A., Ed.; Van Nostrand Reinhold: New York, 1990, p 93.

25. "Synthesis Using Plasmid-Based Biocatalysis: Plasmid Assembly and 3-Deoxy-D-arabino-heptulosonate Production"
Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1990, 112, 1657.

26. "Genomic Direction of Synthesis During Plasmid-Based Biocatalysis"
Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1990, 112, 9630.

27. "Hydrocarbon and Phosphate Triester Formation During Homolytic Hydrolysis of Organophosphonium Ions: An Alternate Model for Organophosphonate Biodegradation"
Avila, L. Z.; Bishop, P. A.; Frost, J. W. J. Am. Chem. Soc. 1991, 113, 2242.

28. "Predicting Inhibition of Dehydroquinate Synthase"
Piehler, L. T.; Montchamp, J.-L.; Frost, J. W.; Manly, C. J. Tetrahedron 1991, 47, 2423.

29. "Metabolites Associated with Organophosphonate C-P Bond Cleavage: Chemical Synthesis and Microbial Degradation of [32P]-Ethylphosphonic Acid"
Avila, L. Z.; Draths, K. M.; Frost, J. W. Bioorg. Med. Chem. Lett. 1991, 1, 51.

30. "Irreversible Inhibition of 3-Dehydroquinate Synthase"
Montchamp, J.-L.; Frost, J. W. J. Am. Chem. Soc. 1991, 113, 6296.

31. "Conversion of D-Glucose into Catechol: The Not-So-Common Pathway of Aromatic Biosynthesis"
Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1991, 113, 9361.

32. "Biocatalytic Synthesis of Aromatics from D-Glucose: The Role of Transketolase"
Draths, K. M.; Pompliano, D. L.; Conley, D. L.; Frost, J. W.; Berry, A.; Disbrow, G.; Starversky, R.; Lievense, J. J. Am. Chem. Soc. 1992, 114, 3956.

33. "Diastereoselection and In Vivo Inhibition of 3-Dehydroquinate Synthase"
Montchamp, J.-L.; Piehler, L. T.; Frost, J. W. J. Am. Chem. Soc. 1992, 114, 4453.

34. "In Vitro and In Vivo Inhibition of Dehydroquinate Synthase"
Frost, J. W.; Piehler, L. T.; Montchamp, Jean-Luc In Biosynthesis and Molecular Regulation of Amino Acids in Plants; Singh, B.; Flores, H.; Shannon, J.C., Ed.; American Society of Plant Physiologists: 1992, pp 163-173.

35. "The Basis for Slowly Reversible Inhibition of Dehydroquinate Synthase: A Case of Mistaken Identity?"
Montchamp, Jean-Luc; Piehler, L. T.; Tolbert, T. J. Bioorg. Med. Chem. Lett. 1992, 2, 1349.

36. "Combining Biocatalysis with Nineteenth Century Organic Chemistry: Conversion of D-Glucose into Quinoid Organics"
Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1992, 114, 9725.

37. "Designing Inhibitors of Dehydroquinate Synthase: Structural Simplicity Versus Inhibitory Potency"
Montchamp, J.-L.; Piehler, L. T.; Tolbert, T. J.; Frost, J. W. Bioorg. Med. Chem. Lett. 1993, 3, 1403.

38. "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"
Dell, K. A.; Frost, J. W. J. Am. Chem. Soc. 1993, 115, 11581.

39. "Phosphonomethylation of Cyclohexene Oxides"
Montchamp, J.-L.; Migaud, M. E.; Frost, J. W. J. Org. Chem. 1993, 58, 7679.

40. "Prospects for Biocatalytic Synthesis of Aromatics in the 21st Century" Frost, J. W.; Lievense, J. New J. Chem. 1994, 18, 341.

41. "Environmentally Compatible Synthesis of Adipic Acid from D-Glucose"
Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1994, 116, 399.

42. "Biocatalytic Desulfurization of Arylsulfonates"
Dudley, M. W.; Frost, J. W. Bioorg. Med. Chem. 1994, 2, 681.

43. "Microbial Biocatalysis: Synthesis of Adipic Acid from D-Glucose"
Draths, K. M.; Frost, J. W. In Alternative Chemical Synthesis for Pollution Prevention; Anastas, P. Ed.; ACS Symposium Series; American Chemical Society: Washington, DC, 1994, Chapter 3, p 32.

44. "Inversion of an Asymmetric Center in Carbocyclic Inhibitors of 3-Dehydroquinate Synthase: Examining and Exploiting the Mechanism for syn-Elimination During Substrate Turnover"
Montchamp, J.-L.; Peng, J.; Frost, J. W. J. Org. Chem. 1994, 59, 6999.

45. "Synthesis and Evaluation of 3-Dehydroquinate Synthase Transition State Analogues"
Montchamp, J.-L.; Frost, J. W. J. Org. Chem. 1994, 59, 7596.

46. "Sweetening Chemical Manufacture"
Frost, J. W.; Draths, K. M. Chemistry in Britain 1995, 31, 206.

47. "Environmentally Compatible Synthesis of Catechol from D-Glucose"
Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1995, 117, 2395.

48. "Inhibition of myo-Inositol-1-phosphate Synthase by a Reaction Coordinate Intermediate"
Migaud, M. E.; Frost, J. W. J. Am. Chem. Soc. 1995, 117, 5154.

49. "Double Arbuzov Reaction of in Situ Generated Bis(trimethylsiloxy)phosphine with Dielectrophiles: Methodology for the Synthesis of Cyclic Phosphinic Acids"
Montchamp, J.-L.; Tian, F.; Frost, J. W. J. Org. Chem. 1995, 60, 6076.

50. "Biocatalytic Syntheses of Aromatics fro D-Glucose: Renewabmle Microbial Sources of Aromatic Compounds"
Frost, J. W.; Draths, K. M. Ann. Rev. Microbiol. 1995, 49, 557.

51. "Elaboration of a General Strategy for Inhibition of MIP Synthase: Active Site Interactions of Analogues Possessing Oxidized Reaction Centers"
Migaud, M. E.; Frost, J. W. J. Am. Chem. Soc. 1996, 118, 495.

52. "Evidence for Acetyl Coenzyme A and Cinnamoyl Coenzyme A in the Anaerobic Toluene Mineralization Pathway in Azoracus tolulyticus Tol-4"
Chee-Sanford, J. C.; Frost, J. W.; Fries, M. R.; Zhou, J.; Tiedje, J. M. Appl. Environ. Microbiol. 1996, 62, 964.

53. "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"
Migaud, M. E.; Chee-Sanford, J. C.; Tiedje, J. M.; Frost, J. W. Appl. Environ. Microbiol. 1996, 62, 974.

54. "2,3-Butane Bisacetal Protection of Vicinal Diequatorial Diols"
Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.

55. "Synthetic Modification of the Escherichia coli Chromosome: Enhancing the Biocatalytic Conversion of Glucose into Aromatic Chemicals"
Snell, K. D.; Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1996, 118, 5605.

56. "Renewable Feedstocks"
Frost, J. W. Chem. Eng. 1996, May 16 (611), 32.

57. "Inhibitor Ionization as a Determinant of Binding to 3-Dehydroquinate Synthase"
Tian, F.; Montchamp, J.-L.; Frost, J. W. J. Org. Chem. 1996, 61, 7373.

58. "Reaction of 3-Dehydroshikimic Acid with Molecular Oxygen and Hydrogen Peroxide: Products, Mechanism, and Associated Antioxidant Activity"
Richman, J. E.; Chang, Y.-C.; Kambourakis, S.; Draths, K. M.; Almy, E.; Snell, K. D.; Strasburg, G. M.; Frost, J. W. J. Am. Chem. Soc. 1996, 118, 11587.

59. "Cyclohexenyl and Cyclohexylidene Inhibitors of 3-Dehydroquinate Synthase: Active Site Interactions Relevant to Enzyme Mechanism and Inhibitor Design"
Montchamp, J.-L.; Frost, J. W. J. Am. Chem. Soc. 1997, 119, 7645.

60. "Crystal Structure of Dehydroquinate Synthase: One Active Site Catalyzes Multiple Chemical Reactions"
Carpenter, E. P.; Hawkins, A. R.; Frost, J. W.; Brown, K. A. Nature 1998, 394, 299.

61. "Improving the Environment Through Process Changes and Product Substitutions"
Draths, K. M.; Frost, J. W. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processes, Anastas, P. T.; Williamson, T. C., Ed.; Oxford University Press: Oxford, 1998.

62. "Synthesis of Vanillin from D-Glucose"
Li, K.; Frost, J. W. J. Am. Chem. Soc. 1998, 120, 10545.

63. "Fed-Batch Fermentor Synthesis of 3-Dehydroshikimic Acid Using Recombinant Escherichia coli "
Li, K.; Mikola, M. R.; Draths, K. M.; Worden, R. M.; Frost, J. W. Biotechnol. Bioeng. 1999, 64, 61.

64. "Shikimic Acid and Quinic Acid: Replacing Isolation from Plant Sources with Recombinant Microbial Biocatalysis"
Draths, K. M.; Knop, D. R.; Frost, J. W. J. Am. Chem. Soc. 1999, 121, 1603.

65. "Synthesis of 1,2,3,4-Tetrahydroxybenzenes from Glucose via myo-Inositol Intermediacy"
Hansen, C. A.; Dean, A. B.; Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1999, 121, 3799.

66. "myo-Inositol 1-Phosphate Synthase: Does a Single Active-Site Amino Acid Catalyze Multiple Proton Transfers"
Tian, F.; Migaud, M. E.; Frost, J. W. J. Am. Chem. Soc. 1999, 121, 5795.

67. Microbial Synthesis of 3-Dehydroshikimic Acid: A Comparative Analysis of D-Xylose, L-Arabinose, and D-Glucose Carbon Sources"
Li, K.; Frost, J. W. Biotechnol. Prog. 1999, 15, 876.

68. "Succinic Acid as a Proform of Phosphoenolpyruvic Acid: Employing Glucose Adjuncts in Microbe-Catalyzed Synthesis"
Li, K.; Frost, J. W. J. Am. Chem. Soc. 1999, 121, 9461.

69. "Synthesis of Gallic Acid: Cu+2-Mediated Oxidation of 3-Dehydroshikimic Acid"
Kambourakis, S.; Frost, J. W. J. Org. Chem. 2000, 65, 6904.

70. "Synthesis of Gallic Acid and Pyrogallol from Glucose: Replacing Natural Product Isolation with Microbial Catalysis"
Kambourakis, S.; Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 2000, 122, 9042.

71. "3-Dehydroshikimic Acid: A Building Block for Chemical Synthesis from Renewable Feedstocks"
Draths, K. M.; Kambourakis, S.; Li, K.; Frost, J. W. In Chemicals and Materials from Renewable Resources; Bozell, J. J., Ed.; ACS Symposium Series 784; American Chemical Society: Washington DC, 2001, Chapter 11, 133.

72. "Aromatic Inhibitors of Dehydroquinate Synthase: Synthesis, Evaluation and Implications for Gallic Acid Biosynthesis"
Chandran, S. C.; Frost, J. W. Bioorg. Med. Chem. Lett. 2001, 11, 1493.

73. "Benzene-Free Synthesis of Phenol"
Gibson, J. M.; Thomas, P. S.; Thomas, J. D.; Barker, J. L.; Chandran, S. S.; Harrup, Draths, K. M.; Frost, J. W. Angew. Chemie, Int. Ed. 2001, 40, 1945.

74. "Microbial Synthesis of p-Hydroxybenzoic Acid from Glucose"
Barker, J. L.; Frost, J. W. Biotechnol. Bioeng. 2001, 76, 376.

75. "Hydroaromatic Equilibration During Biosynthesis of Shikimic Acid"
Knop, D. R.; Draths, K. M.; Chandran, S. S; Barker, J. L.; von Daeniken, R.;Weber, W.; Frost, J. W. J. Am. Chem. Soc. 2001, 123, 10173.

76. "Benzene-Free Synthesis of Hydroquinone"
Ran, N.; Knop, D. R.; Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 2001, 123, 10927.

77. "Chemicals from Plants"
Frost, J. W.; Draths, K. M.; Knop, D. R.; Harrup, M. K.; Barker, J. L.; Niu, W. In Carbon Management: Implications for R&D in the Chemical Sciences and Technology; National Academy Press: Washington DC, 2001, Chap 12, p 185.

78. "Biosynthesis of 1-Deoxy-1-imino-D-erythrose 4-Phosphate: A Defining Metabolite in the Aminoshikimate Pathway"
Guo, J.; Frost, J. W. J. Am. Chem. Soc. 2002, 124, 528.

79. "Deoxygenation of Polyhydroxybenzenes Derived from Glucose: An Alternative Strategy for the Benzene-Free Synthesis of Aromatic Chemicals"
Hansen, C.; Frost, J. W. J. Am. Chem. Soc. 2002, 124, 5926.

80. "Benzene-Free Synthesis of Adipic Acid"
Niu, W.; Draths, K. M.; Frost, J. W. Biotechnol. Prog. 2002, 18, 201.

81. "Kanosamine Biosynthesis: A Likely Source of the Aminoshikimate Pathway's Nitrogen Atom"
Guo, J.; Frost, J. W. J. Am. Chem. Soc. 2002, 124, 10642.

82. "Modulation of Phosphoenolpyruvate Synthase Expression Increases Shikimate Pathway Product Yields in E. coli"
Yi, J.; Li, K.; Draths, K. M.; Frost, J. W. Biotechnol. Prog. 2002, 18, 1141.

83. "Antioxidant Activity of 3-Dehydroshikimic Acid in Liposomes, Emulsions, and Bulk Oil"
Chang, Y.-C; Almy, E. A.; Blamer, G. A.; Gray, I. A.; Frost, J. W.; Strasburg, G. M. J. Agric. Food Chem. 2003, 51, 2753.

84. "Phosphoenolpyruvate Availability and the Biosynthesis of Shikimic Acid"
Chandran, S. C.; Yi, J.; Draths, K. M.; von Daeniken, R.; Weber, W.; Frost, J. W. Biotechnol. Prog. 2003, 19, 808.

85. "Altered Glucose Transport and Shikimate Pathway Product Yields in E. coli"
Yi, J.; Draths, K. M.; Li, K.; Frost, J. W. Biotechnol. Prog. 2003, 19, 1450.

86. "Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol"
Niu, W.; Molefe, M. N.; Frost, J. W. J. Am. Chem. Soc. 2003, 125, 12998.

87. "Rational Pathway Engineering of Type I Fatty Acid Synthase Allows the Biosynthesis of Triacetic Acid Lactone from D-Glucose in Vivo"
Zha, W.; Shao, Z.; Frost, J. W.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 4534.

88. "Synthesis of Aminoshikimic Acid"
Guo, J.; Frost, J. W. Org. Lett. 2004, 6, 1585.

89. "Creation of a Shikimate Pathway Variant"
Ran, N.; Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 2004, In press.


PATENTS AND PENDING APPLICATIONS
1. Title: Method of Controlling Gene Expression
Inventors: N. K. Peters, J. W. Frost, S. R. Long
Patent No. 5,070,018
Date of Patent: December 3, 1991

2. Title: Biosynthetic Production of Common Aromatic Pathway Compounds
Inventors: J. W. Frost
Patent No. 5,168,056
Date of Patent: December 1, 1992

3. Title: Capillary Electrophoretic System
Inventors: Richard N. Zare, Stephen L. Pentoney, Jr., John W. Frost, Jeff Quint
Patent No. 5,232,565
Date of Patent: August 3, 1993

4. Title: Biocatalytic Synthesis of Catechol from D-Glucose
Inventors: J. W. Frost, K. M. Draths
Patent No. 5,272,073
Date of Patent: December 21, 1993

5. Title: Synthesis of Adipic Acid from Biomass-Derived Carbon Sources
Inventors: John W. Frost, Karen M. Draths
Patent No: 5,487,987
Date of Patent: January 30, 1996

6. Title: Bacterial Cell Transformants for Production of cis,cis-Muconic Acid and Catechol
Inventors: John W. Frost, Karen M. Draths
Patent No. 5,616,496
Date of Patent: April 1, 1997

7. Title: Synthesis of Catechol from Biomass-Derived Carbon Sources
Inventors: John W. Frost, Karen M. Draths
Patent No. 5,629,181
Date of Patent: May 13, 1997

8. Title: Deblocking the Common Pathway of Aromatic Amino Acid Synthesis
Inventors: John W. Frost, Kristi D. Snell, Karen M. Draths
Patent No. 5,776,736
Date of Patent: July 7, 1998

9. Title: Synthesis of Quinic Acid from Glucose
Inventors John W. Frost, Karen M. Draths, Timothy L. Ward
Patent No. 5,798,236
Date of Patent: August 25, 1998

10. Title: Antioxidant Activity of 3-Dehydroshikimates
Inventors: John W. Frost
Patent No. 5,821,266
Date of Patent: October 13,1998

11. Title: Synthesis of Vanillin from a Carbon Source
Inventors: John W. Frost
Patent No. 6,372,461
Date of Patent: April 16, 2002

12. Title: Biocatalytic Synthesis of Shikimic Acid
Inventors: John W. Frost, Karen M. Frost, David R. Knop
Patent No. 6,472,169
Date of Patent: October 29, 2002

13. Title: Biocatalytic Synthesis of Galloid Organics
Inventors: John W. Frost
Patent No. 6,472,190
Date of Patent: October 29, 2002

14. Title: Biocatalytic Synthesis of Quinic Acid and Conversion to Hydroquinone
Inventors: John W. Frost, Karen M. Frost
Patent No. 6,600,077
Date of Patent: July 29, 2003

15. Title: Biocatalytic Synthesis of Quinic Acid and Conversion to Hydroquinone
Inventors: John W. Frost, Karen M. Frost
Patent No. 6,620,602
Date of Patent: September 16, 2003

DISSERTATIONS
1. "Enzyme-Targeted Disruption of Aromatic Amino Acid Biosynthesis in Plants"
D. L. Pompliano, Ph.D. Dissertation, December 1987.

2. "Inhibitors of Dehydroquinate Synthase: Synthesis and Evaluation of Herbicidal Activity"
L. M. Reimer, Ph. D. Dissertation, October 1988.

3. "Genetic Studies of the Biodegradation of Organophosphonates by Escherichia coli "
S. H. Loo, Ph.D. Dissertation, March 1990.

4. "Elucidation of Escherichia coli -Mediated Carbon to Phosphorus (C-P) Bond Cleavage"
L. Z. Avila, Ph.D. Dissertation, January 1991.

5. "Microbial Biocatalysis: Synthesis of Aromatics from D-Glucose"
K. M. Draths, Ph.D. Dissertation, June 1991.

6. "Synthesis and Evaluation of Carbocyclic Inhibitors of Dehydroquinate Synthase"
L. T. Piehler, Ph.D. Dissertation, August 1991.

7. "Degradation of Aliphatic Organosulfonic and Organophosphonic Acids by Escherichia coli "
K. J. Stimpfl, M.S. Dissertation, August 1992.

8. "Mechanism-Based Carbocyclic Inhibitors of Dehydroquinate Synthase"
J.-L. Montchamp, Ph.D. Dissertation, December 1992.

9. "Biocatalytic Synthesis of Quinic Acid and Application to the Production of Commercial Quinoid Organic Products"
T. L. Ward, M.S. Dissertation, May 1993.

10. "Biocatalytic Conversion of D-Glucose into Aromatics"
Kristi A. Dell, Ph.D. Dissertation, December 1993.

11. "Biocatalytic Production of Aromatics from D-Glucose"
Michael A. Farabaugh, M.S. Dissertation, February 1996.

12. "Investigation of myo-Inositol 1-Phosphate Synthase Catalytic Sequence Utilizing Mechanism-Based Inhibitors"
Marie E. Migaud, Ph.D. Dissertation, July 1996.

13. "Mechanistic Studies and Inhibition of Dehydroquinate Synthase and myo-Inositol 1-Phosphate Synthase"
Jirong Peng, Ph. D. Dissertation, December 1996.

14. "Optimization of Biocatalytic 3-Dehydroshikimic Acid Production from D-Glucose in Escherichia coli "
Mark R. Mikola, M.S. Dissertation, January 1997.

15. "Mechanism-Based Inhibition of 3-Dehydroquinate Synthase and myo-Inositol 1-Phosphate Synthase"
Feng Tian, Ph.D. Dissertation, December 1998.

16. "Microbial Synthesis of Value-Added Chemicals from D-Glucose"
Kai Li, Ph.D. Dissertation, August 1999.

17. "Synthesis of Value-Added Chemicals from Glucose Using Chemical and Microbial Catalysis: Gallic Acid, Protocatechuic Acid, Pyrogallol, and Catechol"
Spiros Kambourakis, Ph.D. Dissertation, February 2000.

18. "Manipulation of the Genes and Enzymes of the Shikimate Pathway"
Sunil S. Chandran, Ph.D. Dissertation, January 2001.

19. "Environmentally Benign Synthesis of Aromatic Coupounds from D-Glucose"
Jessica L. Barker, Ph.D. Dissertation, January 2001.

20. "Chemo-Enzymatic Synthesis of Aromatics via Non-Shikimate Pathway Intermediates"
Chad A. Hansen, Ph.D. Dissertation, March 2002.

21. "Hydroaromatic Equilibration During Shikimic Acid and Quinic Acid Biosynthesis"
David R. Knop, Ph.D. Dissertation, February 2002.

22. "Studies for Enhancing Carbon Flow Through the DXP and Shikimate Pathway"
Padmesh Venkitasubramanian, Ph.D. Dissertation, June 2003.

23. “Increasing the Carbon Flow into the Aromatic Common Pathway: Biosynthesis of 3-Dehydroshikimic Acid from D-Glucose”
Jian Yi, Ph.D. Dissertation, 2004.

24. “Biosynthesis of Precursors to the Aminoshikimate Pathway and Microbial Synthesis of 5-Amino-5-Deoxyshikimate”
Jiantao Guo, Ph.D. Dissertation, 2004.


ORGANIZER/FACILITATOR/PARTICIPANT
August 13-14, 1987 "Environmental Chemistry and Chemical Processes"
National Science Foundation Workshop
Chairman and Organizer

May 2-3, 1988 "Strategies and Opportunities at the Interface Between Chemistry, Chemical Engineering and Life Sciences"
The 39th Industrial Affiliates Symposium, Stanford Univ.
Coorganizer

March 5-6, 1992 "Workshop in Environmental Chemistry"
National Science Foundation
Coorganizer

April 27-28, 1992 "Molecular Aspects of Biocatalysis"
May 20-21, 1992 Short Course created for American Cyanamid

July 6-10, 1992 "Biocatalysis"
Gordon Research Conference
Cochairman

March 10, 1994 Council for Chemical Research, Organizing Committee
CCR Workshop on Environmental Chemistry

July 12-13, 1994 U.S. Environmental Protection Agency and the
National Science Foundation
"Workshop on Green Syntheses and Processing in Chemical Manufacturing"
Served as facilitator for the benign organic synthesis working group.

March 22, 1995 National Institutes of Health
"Metabolic Engineering Workshop"
This gathering advised NIH on the establishment of an initiative in metabolic engineering.

July 31-Aug. 1, 1996 The Ohio State University
Guest Lecturer: Summer Microbial Physiology Course

Nov. 7, 1996 Environmental Protection Agency, Washington, DC
Instructor for Short Course: "Chemical Manufacture in a Sustainable Economy: Use of Microbes as Synthetic Catalysts"

January 19 - 22, 1999 Participant, EPA/NSF Joint Technology for a Sustainable Environment Review Workshop, Washington, DC

May 2-6, 1999 Session Chairman/Organizer, "Industrial Chemicals" 21st Symposium on Biotechnology for Fuels and Chemicals, Fort Collins, CO

May 26-27, 1999 CoChairman, NSF/DOE "Workshop on Molecular Energy and Environmental Science" Chicago, IL

March 24-26, 2000 DARPA
"Next Generation Green Synthesis: Experimental and Theoretical Approaches to New Enzymes, Pathways, and Biomimetic Catalysts"
Herdon, VA

December 9-10, 2000 Chemical Sciences Roundtable of the National Research Council
"Carbon Management: Implications for R&D in the Chemical Sciences"Washington, DC

May 14-16, 2002 U.S. Department of Energy (DOE) Catalysis Workshop
Gaithersburg, MD
Organized the biocatalysis working group and authored sections dealing with biocatalysis in the report entitled "Opportunities for Catalysis Science in the 21st Century"


INVITED SCHOLARLY PRESENTATIONS (since 1994)
Michigan State University
Symposium: "Materials Design for the Environment"
East Lansing, Michigan-February 12, 1994

Boehringer Ingelheim Pharmaceuticals, Inc.
Ridgefield, Connecticut-May 3, 1994

Ciba-Geigy Corporation
Ardsley, New York-May 5, 1994

Haarmann & Reimer Corporation
Elkhart, IN-May 25, 1994

Joint Central-Great Lakes
Regional ACS Meeting
Symposium on Natural Products Chemistry
Ann Arbor, MI-June 1-3, 1994

National Corn Growers Association
Corn Utilization Conference V
"New Polymeric Materials from Corn"
St. Louis, MO-June 8-10, 1994

Catalysis Gordon Conference
Colby-Sawyer College, New London, NH-June 26-July 1, 1994

Symposium:
"The Role of Microbes in Biotechnology:
Where Does the Future Lie?"
-Marine Biological Laboratory Woods Hole, MA-July 9, 1994

Biocatalysis Gordon Conference
Kimball Union Academy, Meriden, NH-July 10-15, 1994

ACS National Meeting
Division of Environmental Chemistry
"Designing Chemical Syntheses and
Processes for the Environment", Washington, DC-August 21, 1994

Bio-Technical Resources
Manitowoc, WI-September 15, 1994

National Institutes of Health
Bethesda, MD-January 6, 1995

Hope College
Department of Chemistry
Holland, MI-January 20, 1995

General Electric
Schenectady, NY-February 23, 1995

Clarkson College
Department of Chemistry
Potsdam, NY-February 24, 1995

ACS National Meeting
Division of Biochemical Technology
"Fermentation Technologies to Utilize Agricultural Residues"
Anaheim, CA-April 6, 1995

"Wither Enzymology"
Jeremy Knowles' 60th Birthday
Harvard University, Cambridge, MA-April 28-30, 1995

Gordon Research Conference on Bioorganic Chemistry
Proctor Academy, Andover, NH-June 18-23, 1995

The Upjohn Company
Kalamazoo, MI-July 19, 1995

Vertex Pharmaceuticals Inc.
Altus Biologic
Cambridge, MA-August 9, 1995

Calvin College
Department of Chemistry, Grand Rapids, MI-September 22, 1995

Wayne State University
Department of Pharmaceutical Sciences
Detroit, MI-November 15, 1995

Cargill
Minneapolis, MN-December 6, 1995

InBio'96
"Industrial Biocatalysis, Making it Happen"
UMIST
Manchester, UK-February 21-21, 1996

Oxford University
The Dyson Perrins Laboratory
Oxford, UK-February 23, 1996

University of Nebraska
Department of Biochemistry
Lincoln, NE-March 12, 1996

Wayne State University
Department of Chemistry
Detroit, MI-April 1, 1996

SmithKline Beecham Pharmaceuticals
King of Prussia, PA-April 18, 1996

Gordon Research Conference
"Environmentally Benign Organic Synthesis"
New England College
Henniker, NH-July 21-26, 1996

20th IUPAC Symposium on the Chemistry of Natural Products
Chicago, IL-September 20, 1996

52nd ACS Fall Scientific Meeting
Midland, MI-October 26, 1996

University of Louisville
Center for Chemical Catalysis
Louisville, KY-March 14, 1997

Green Chemistry and Engineering Conference
Washington, DC-June 23, 1997

"Organic Chemistry and Catalysis"
An International Symposium on the Occasion of the 65th Birthday of Profesor Herman van Bekkum
Technische Universiteit Delft Delft
The Netherlands-October 2-3, 1997

Olivet Nazerene University
Kankakee, IL-March 13, 1998

Roche Pharmaceuticals
Basel, Switzerland-April 19-21, 1998

"Twentieth Symposium on Biotechnology for Fuels and Chemicals"
Gatlinburg, TN-May 3-7, 1998

Dow Chemical Company
Midland, MI-June 17, 1998

2nd Annual Green Chemistry and Engineering Conference
Washington, DC-June 30 - July 2, 1998

Biocatalysis Gordon Conference
Meriden, NH-July 5-10, 1998

Gilead Sciences
Foster City, CA-August 3, 1998

American Chemical Society National Meeting
Boston, MA-August 23-27, 1998

Dow Biotechnology Advisory Board
Grand Rapids, MI-October 1 - 3, 1998

Gilead Sciences
Foster City, CA-October 7, 1998

Southern Methodist University
Department of Chemistry
Dallas, TX-November 9, 1998

Texas Christian University
Department of Chemistry
Fort Worth, TX-November 10, 1998

Florida Environmental Conference
University of Florida
Gainesville, FL-December 1-5, 1998

Givaudan Roure Flavors
Cincinnati, OH-March 12, 1999

Dupont
"Horizons in Biotechnology" Lecture Series
Wilmington, DE-April 16, 1999

University of Wisconsin
School of Pharmacy
Madison, WI-May 7, 1999

Green Chemistry Gordon Conference
Oxford, UK-July 11-16, 1999

Society for Industrial Microbiology
50th Anniversary Annual Meeting
Arlington, VA-August 1-6, 1999

University of Iowa
Biocatalysis and Bioprocessing Conference
"Green Chemistry Perspectives"
Iowa City, IA-October 25-26, 1999

55th ACS Fall Scientific Meeting
Midland Section
Midland, MI-October 30, 1999

University of South Carolina
Department of Chemistry
Columbia, SC-November 3, 1999

University of Illinois
Department of Chemistry
Champaign-Urbana, IL-November 17, 1999

Colorado State University
"Boehringer Ingelheim Distinguished Lecturer"
Department of Chemistry
Fort Collins, CO-January 10, 2000

2000 AAAS Annual Meeting
"Sustainability Through Science"
Washington, DC-February 20, 2000

Davidson College
Department of Chemistry
Davidson, NC-February 10, 2000

Andrews University
Department of Chemistry and Biochemistry
Berrien Springs, MI-April 5, 2000

National Research Council
Biotechnology Research Institute
Montreal Quebec, Canada-April 7, 2000

Polytechnic University
Department of Chemistry
Brooklyn, NY-April 26, 2000

DSRC/DARPA AgBio Conference
La Jolla, CA-July 14, 2000

Naval Surface Warfare Center
Dahlgren, VA-August 9, 2000

DSM Research
"Distinguished Lecturer Series"
Geleen, The Netherlands-August 28, 2000

Biotechnology 2000
"Application of Metabolic Engineering"
Berlin, Germany-September 4, 2000

Office of Naval Research
"Coolfont IV"
Berkeley Springs WV-November 8-12, 2000

Rice University
Department of Biochemistry and Cell Biology
Houston, TX-November 20, 2000

Office of Naval Research Program Review
Washington, DC-January 25, 2001

The University of Toledo
Department of Chemistry
Toledo, OH-February 19, 2001

Cargill
Specialty Food Ingredients
Wayzata, MN-February 23, 2001

Dow Chemical
"Carbohydrate Raw Materials as Feedstocks for Industrial Chemicals Using Chemical Transformations"
Midland, MI-August 21, 2001

CHEMRAWN
"Emerging Opportunities in the New Biotech/Biobased Economy"
University of Colorado
Boulder, CO-June 11, 2001

Diversa Corporation
San Diego, CA-July 23, 2001

BioTrans 2001
"5th European Conference on Biocatalysis and Biotransformations"
Darmstadt Univ. of Technology
Darmstadt, Germany-September 6, 2001

Roche Research Laboratories
Basel, Switzerland-September 10, 2001

Bradley University
Department of Chemistry
Peoria, IL-October 25, 2001

National Center for Agricultural Utilization Research
Peoria, IL-October 26, 2001

Environmental Biotechnology Seminar Series
University of Connecticut
Storrs, CT-February 27, 2002

Merck Research Laboratories
Academic Speakers Program
Rahway, NJ-March 27, 2002

Plenary Talk
"Opportunities for Catalysis/Nanoscience"
Gaithersburg, MD-May 14, 2002

Cargill
Minneapolis, MN-July 10, 2002

Grand Valley State University
Allendale , MI-November 1, 2002

Iowa State University
Ames, IA-April 4, 2003

Office of Naval Research Program Review
"Coolfont V"
Coolfont, WV-April 9-13, 2003

Pfizer Seminars in Medicinal Chemistry
Interdisciplinary Program in Medicinal Chemistry
University of Michigan
Ann Arbor, MI-September 25, 2003

ONR Biomimetics Program Site Visit
Naval Surface Warfare Center
Indian Head Division
Indian Head, MD-October 2, 2003

Enzyme Engineering XVII
Sante Fe, NM-November 9-14, 2003

BMBB/Biotechnology Institute
University of Minnesota
St. Paul, MN-January 22, 2004

Department of Chemistry
Pennsylvania State University
University Park, PA-January 26-27, 2004

World Congress on Industrial Biotechnology and Bio Processing
Orlando, FL-April 23, 2004

Department of Chemistry
University of Hong Kong
Hong Kong-May 7, 2004

Department of Chemistry
The Chinese University of Hong Kong
Hong Kong-May 10, 2004

Department of Chemistry
The Hong Kong University of Science and Technology
Hong Kong-May 11, 2004