Co-Deputy Director, Vanderbilt Center in Molecular Toxicology
office: 615-322-6100
FAX: 615-343-1234
email: c.j.rizzo@vanderbilt.edu
B.A., 1984, Temple University
Ph.D., 1990, University of Pennsylvania (Amos B. Smith, III)
NIH Postdoctoral Research Associate, 1990-92, Columbia University (Ronald Breslow)
Assistant Professor of Chemistry, Vanderbilt University, 1992-1999
Associate Professor of Chemistry, Vanderbilt University, 1999-2005
Professor of Chemistry, Vanderbilt University, 2006-present
Associate Member, Vanderbilt-Ingram Cancer Center at Vanderbilt, 1993-present
Mentor, Research at the Chemistry/Biology Interface Program, 2000-present
Center Investigator, Center in Molecular Toxicology, 2001-present
Member, Vanderbilt Chemical & Physical Biology Program, 2001-present
Member, Vanderbilt Institute of Chemical Biology, 2002-present
American Cancer Society, Junior Faculty Research Award, 1994-96
National Institutue of Environmental Health Sciences Review Committee, 7/03 - 6/07
Editorial Board, Chemical Research in Toxicology, 2006-2009
Research Interests: Synthetic, Mechanistic and Bio-organic chemistry
Chemistry and Biology of DNA-Carcinogen Adducts
Covalent modification of DNA by electrophiles is the initial step in chemical carcinogenesis. If these modifications are not repaired, they compromise the fidelity of DNA replication leading to mutations and possibly cancer. To properly study the mutagenic effects and repair of these lesions, oligonucleotides containing structurally defined carcinogen adducts are required. We are currently developing versatile synthetic strategies for the synthesis of oligonucleotides, which are site-specifically modified by carcinogens. We have focused on two class of DNA-carcinogen adducts. The first are C8-deoxyguanosine adducts of aryl amines such as IQ, which is found in cooked meats. We are also synthesizing 1,N2-deoxyguanosine adducts of lipid peroxidiation products such as 4-hydroxynonenal.
Representative Publications:
Cho YJ, Kim HY, Huang H, Slutsky A, Minko IG, Wang H, Nechev LV, Kozekov ID, Kozekova A, Tamura P, Jacob J, Voehler M, Harris TM, Lloyd RS, Rizzo CJ, Stone MP. Spectroscopic characterization of interstrand carbinolamine cross-links formed in the 5'-CpG-3' sequence by the acrolein-derived gamma-OH-1,N2-propano-2'-deoxyguanosine DNA adduct. Journal of the American Chemical Society, 2005, 127: 17686-17696.
Goodenough AK, Kozekov ID, Zang H, Choi JY, Guengerich FP, Harris TM, Rizzo CJ. Site specific synthesis and polymerase bypass of oligonucleotides containing a 6-hydroxy-3,5,6,7-tetrahydro-9H-imidazo[1,2-a]purin-9-one base, an intermediate in the formation of 1,N2-etheno-2'-deoxyguanosine. Chemical Research Toxicology, 2005 18:1701-1714.
Zang H, Goodenough AK, Choi JY, Irimia A, Loukachevitch LV, Kozekov ID, Angel KC, Rizzo CJ, Egli M, Guengerich FP. DNA adduct bypass polymerization by Sulfolobus solfataricus DNA polymerase Dpo4 - Analysis and crystal structures of multiple base pair substitution and frameshift products with the adduct 1,N2-ethenoguanine. Journal of Biological Chemistry, 2005, 280: 29750-29764
Scholdberg TA, Merritt WK, Dean SM, Kowalcyzk A, Harris CM, Harris TM, Rizzo CJ, Lloyd RS, Stone MP. Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adduct in the human N-ras Codon 61 sequence. Biochemistry, 2005, 44: 3327-3337.
Stover JS, Rizzo CJ, Synthesis of the N2-Deoxyguanosine Adduct of the Potent Dietary Mutagen IQ. Organic Letters, 2004, 6: 4985-4988.
Elmquist CE, Stover JS, Wang Z, Rizzo CJ, Site-Specific Synthesis and Properties of Oligonucleotides Containing C8-Deoxyguanosine Adducts of the Dietary Mutagen IQ. Journal of the American Chemical Society, 2004, 126: 11189-11201.
Wang, H; Marnett, LJ.; Harris, TM.; Rizzo, CJ. A Novel Synthesis of Malondialdehyde Adducts of Deoxyguanosine, Deoxyadenosine and Deoxycytidine. Chemical Research in Toxicology, 2004, 17: 144-149.
Wang H, Kozekov ID, Harris TM, Rizzo CJ, Site-Specific Synthesis and Reactivity of Oligonucleotides Containing Stereochemically Defined 1,N2-Deoxyguanosine Adducts of the Lipid Peroxidation Product trans-4-Hydroxynonenal. Journal of the American Chemical Society, 2003, 125: 5687-5700.
Kozekov ID, Nechev LV, Mosely MD, Harris CM, Rizzo CJ, Stone MP, Harris TM, DNA Interchain Cross-links Formed by Acrolein and Crotonaldehyde. Journal of the American Chemical Society, 2003, 125: 50-61.
Fernandes PH, Wang H, Rizzo, CJ and Lloyd RS, Site-Specific Mutagenicity of Stereochemically Defined 1,N2-Deoxyguanosine Adducts of 4-Hydroxynonenal in Mammalian Cells. Environmental and Molecular Mutagenesis, 2003, 42: 68-74.
"Coupling Products of Nucleosides with the Glyoxal Adduct of Deoxyguanosine" Angela K. Brock, Ivan D. Kozekov, Carmelo J. Rizzo, and Thomas M. Harris, Chemical Research in Toxicology 2004, 17, 1047-1056.
"Stereoselective Synthesis of the 1,N2-Deoxyguanosine Adducts of Cinnamaldehyde. A Stereocontrolled Route to Deoxyguanosine Adducts of alpha,beta-Unsaturated Aldehydes. " Mansoureh Rezaei, Thomas M. Harris, Carmelo J. Rizzo, Tetrahedron Letters, 2003, 44, 7513-7516.
"Synthesis of the C8-Deoxyguanosine Adduct of the Food Mutagen IQ." Zhiwei Wang and Carmelo J. Rizzo, Organic Letters, 2001, 3, 565.
"Stereocontrolled Syntheses of All Four Stereoisomeric 1,N2-Deoxyguanosine Adducts of the Lipid Peroxidation Product trans-4-Hydroxynonenal." Hao Wang and Carmelo J. Rizzo. Organic Letters, 2001, 3, 3603.
"DNA Adducts of Acolein: Site-specific Synthesis of an Oligonucleotide Containing 6-Hydroxy-5,6,7,8-tetrahydropyrimido[a,2-a]purin-10(3H)-one, an Acolein adduct of Guanine." Lubo V. Neechev, Angela K. Brock, Carmelo J. Rizzo, Thomas M. Harris, Chemical Research in Toxicology, 2002, 15, 607.
Chemistry of Nucleosides and Oligonucleotides
Nucleosides and nucleoside analogs are an established and clinically proven class of thearapeutic agents possessing anticancer and antiviral activity. Oligonucleotides with modified bases and backbones play a central role in the deveopment of genetic therapies such as those involving triplex (antigene) and antisense strategies. We are devloping new and more efficient methods for the synthesis of deoxynucleosides and applying these methods to the synthesis of nucleosides with modified bases. Our overall strategy is shown below. We have be able to efficiently prepare glycosylation precursor in which the hydroxyl group which we wish to deoxygenated is strategically protected with a benzoyl or m-(trifluoromethyl)benzoyl group. After glycosylation, the desired hydroxyl group is deoxygenated via a photoinduced electron-transfer (PET) mechanism using substituted carbazoles as the photosensitizer.
Representative Publications:
"Stereocontrolled, De Novo Synthesis of beta-2 '-Deoxyribonucleosides." Minnie Park and Carmelo J. Rizzo, Journal of Organic Chemistry 1996, 61, 6092.
"An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and m-(Trifluoromethyl)benzoates." Daniel R. Prudhomme, Zhiwei Wang and Carmelo J. Rizzo, Journal of Organic Chemistry 1997, 62, 8257.
"Stereocontrolled Synthesis of alpha-2 '-Deoxyribonucleosides," Zhiwei Wang and Carmelo J. Rizzo, Tetrahedron Letters, 1997, 38 , 8177.
"A Convenient Synthesis of 3,6-Substituted Carbazoles via Nickel Catalyzed Cross-Coupling." Minnie Park, Jason R. Buck and Carmelo J. Rizzo, Tetrahedron 1998, 54, 12707.
"Regioselective Synthesis of beta-N1 and beta N3-Alloxazine Nucleosides." Zhiwei Wang, Carmelo J. Rizzo, Organic Letters 2000, 2 , 227.
"Synthesis of Deoxyribonucleosides: beta-3',5'-Di-O-benzoylthymidine." Daniel R. Prudhomme, Minnie Park, Zhiwei Wang, Jason R. Buck and Carmelo J. Rizzo, Organic Syntheses 1999, 77, 162.
"3,6-Dimethyl-9-ethylcarbazole (DMECZ)." Jason R. Buck, Minnie Park, Zhiwei Wang, Daniel R. Prudhomme and Carmelo J. Rizzo, Organic Syntheses 1999, 77, 153.
"Stereocontrolled Synthesis of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl Protected Ribo- and Arabinonucleosides." Zhiwei Wang, Daniel R. Prudhomme, Jason R. Buck, Minnie Park and Carmelo J. Rizzo, Journal of Organic Chemistry 2000, 65, 5969.
Chemical Models for Flavoenzyme Catalysis
Flavoenzyme are versatile biological redox catalysts which utilize derivatives of riboflavin (vitamin B2) to mediate electron-transfer. We are developing chemical models to determine how the interactions with the protein environment modulates the redox and catalytic properties of the flavin coenzyme. Such interactions include conformation, electronic effects, hydrogen bonding, electrostatic interactions and pi-statcking.
Representative Publications:
"A 'One-Pot' Alkylation/Hydrolysis of o-Nitrotrifluoroacetanilides. A Convenient Route to N-Alkyl o-Phenylenediamines." Samuel A. Brown and Carmelo J. Rizzo, Synthetic Communications 1996, 26 , 4065.
"Conformational Effects on Flavin Redox Chemistry." Justin J. Hasford, William Kemnitzer and Carmelo J. Rizzo, Journal of Organic Chemistry 1997, 62, 5224.
"Linear Free Energy Substituent Effect on Flavin Redox Chemistry." Justin J. Hasford and Carmelo J. Rizzo, Journal of the American Chemical Society 1998, 120, 2251.
"Reduction of Hg(II)-EDTA by Conformationally Biased Flavin." Justin J. Hasford and Carmelo J. Rizzo, Tetrahedron Letters 1998, 39, 1317.
"X-Ray Crystal Structures of Conformationally Biased Flavin Models." Joseph H. Reibenspies, Fengli Guo and Carmelo J. Rizzo Organic Letters 2000, 2 , 903-906.
Further Conputational Studies on 1,5-Dihydrolumiflavin." C. J. Rizzo, Antioxidants and Redox Signaling, 2001, 3, 737. (invited contribution)
"An N1 Hydrogen-Bonding Model for Flavin Coenzyme." Fengli Guo, Bryan H. Chang and Carmelo J. Rizzo, Bioorganic and Medicinal Chemistry Letters, 2001, 11, 151.
Rizzo Group:
Post-Doctoral Research Associates:
Minnie Park, Ph.D., 1995, Mississippi State University (Keith Mead). Research Fellow at the Fredrick Cancer Research and Development Center, working with Christopher J. Michejda. Currently a RibX Pharmaceuticals, New Haven, CT.
Zhiwei Wang, Ph.D., 1996-2001, Lanzhou University (Yulin Li); Research Scientist at ISIS Pharmaceutical, Carlsbad, CA, 2001-2004; currently a Research Scientist at the Genomics Institute of the Novartis Research Foundation, San Diego, CA
Fengli Guo, Ph.D., 1996, Lanzhou University (Zhongli Liu), Currently an Associate Research Scientist at Pfizer, Inc., San Diego, CA
Ravi Kumar Jalluri 2002-2005, Ph. D., Osmania University, Hyderabad, India (Apurba Datta).
Katya Petrova, 2004- present, Ph. D., Sofia University, Sofia, Bulgaria.
Graduate Students:
Jacqueline D. Brisbane, B. A., 1993, Fisk University , M. S., 1995 , M. S. Thesis: "Regioselective Synthesis and Deoxygenation of Thionobenzoates"
John S. Siler, B. A., 1993, Cumberland College, M. S., 1995 , M. S. Thesis: "2,2 '-Functionalization of 1,1'-Binapthyl-2,2'-bis-triflate
M. Sharon A. Parker, B.S., 1992, Austin Peay State University, Ph.D., 1999, Ph.D. Thesis: "Synthetic Approaches to the Use of Enediynes in the Design of Chemotherapeutic Agents." 1999-2000, Post-doctoral Research Associate with Professor Ned Porter. Currently an Assistant Professor of Austin Peay State University, Clarksville, TN.
Daniel R. Prudhomme, B.S., 1995, College of Holy Cross, Ph. D. 2002, Thesis: "An Improved de Novo Synthesis of 2'-Deoxynucleosides via Photochemical Deoxygenation of Ribonucleosides." Post-doctoral Research Associate with Professor Larry Marnett, Department of Biochemistry, Vanderbilt University School of Medicine, 2002-2004; currently a Research Scientist at Mylan Pharmaceuticals, Morgantown, WV.
Jason R. Buck, B.S., 1994, Xavier University, Ph. D., 2002, Thesis: "Stereocontrolled de Novo Synthesis of 2',3'-Dideoxynucleosides via Photoinduced Electron Transfer Deoxygenation." Currently a working Illumina, Inc., San Diego, CA.
Samuel A. Brown, B.S., 1995, Morehouse College, M.A., Vanderbilt University, currently an Assistant Professor of Chemistry at Tennessee State University, Nashville, TN.
Hao Wang, B.S., 1982, Heifei University of Technology; M.S., 1999, Tennessee Technological University (Dale D. Ensor); Ph. D., 2003, Vanderbilt University, Thesis: "DNA Adducts Derived from Lipid Peroxidation. Site-Specific Synthesis and Reactivity of Oligonucleotides Containing Stereochemically Defined Trans-4-Hydroxynonenal and Malondialdehyde Adducts." Currently a Post-Doctoral Research Associate at Vanderbilt University
David A. Jones, M.S., 2003, Vanderbilt University, Thesis: " The Effects of an N1-Hydrogen Bond on the Redox Properties of Flavoenzyme Catalysis." Currently employed at TestAmerica, Inc.
Kris H. Franklin, M.S.2004, Vanderbilt University, Thesis: "Amino Acid and Peptide Promoted Catalysis of 1,N2 Hydroxypropano Adducts of Deoxyguanosine: A Biomimetic Model for the Interaction of ±,&Mac178;-Unsaturated Aldehydes With DNA." Currently employed at Merck & Co., Rahway, NJ
Angela Brock, B.S.,2000, Knox College.; Ph. D., 2005, Vanderbilt University, Thesis: "DNA Adducts of Bis-Electrophiles" Currently a Post-doctoral Research Associate at the Wadsworth Center, New York State Dept. of Health, with Robert Turesky.
C. Eric Elmquist, B.S., 2000, University of South Florida ; Ph. D., 2005, Vanderbilt University, Thesis: "Site-Specific Synthesis and Analysis of Oligonucleotides Containing the C8-Deoxyguanosine Adducts of the Dietary Mutagen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)." Currently a Post-Doctoral Research Associate in the Division of Biological Engineering at MIT with Peter C. Dedon
James S. Stover, B. S. 2001, University of Virginia, Ph. D., expected 2006
Plamen Christov, B. S. University of Sofia.
Craig A. Garmendia, B. S., 2004 Florida International University;
Undergraduates:
William Kemnitzer, B.A. 1993; Ph.D., 1998, in Chemistry from the University of South Carolina with Professors T. Bryson and J. Dawson. Post-doctoral Research Associate at the University of California, Irvine with Professor James Nowick. Currently a research scientist at Maxim Pharmaceutical in San Diego, CA.
Katheryn E. Garretson, B.A. 1996, MPH, 1996 from the University of Alabama, Birmingham; presently employed by Covance Clinical and Periapproval Services, Inc.
Rongson Pongdee, B. A., 1997, Vanderbilt University, Ph. D., Texas A&M University with Professor Gary Sulikowski.; Post-Doctoral Research Associate at the University of Texas (Ben Lui). Currently an Assistant Professor of Chemistry at Colorado College (Colorado Springs, CO).
Justin J. Hasford, B.S. (High Honors), 1998. Vanderbilt University, Honors Thesis: "Conformational and Electronic Control of Flavin Redox Chemistry.: J. D., 2003, University of Virginia, School of Law. Currently an Associate at Finnegan, Henderson, Farabow, Garrrett and Dunner (Washington, DC).
Bryan H. Chang, B.A., 2000, Vanderbilt University; 2000-2003, Scientist, Chiron, Inc. (Moutainview, CA). Currently a graduate student in the Department of Chemistry & Chemical Biology, Harvard University with Professor Gavin MacBeath.
Stephen Duncan, B.A, 2003, Vanderbilt University, currently a medical student at Vanderbilt University, School of Medicine.
Andrew T. Voglewede, B. S., 2005, currently a medical at the University of Virginia, School of Medicine.
Julia A. Jacobs, B. A., 2005, currently a medical student at the University of Louisville, School of Medicine.
Group picture (April 1997) taken at a symposium to mark the dedication of the New Chemistry Building at Vanderbilt University with two of the symposium speakers, Professor Ronald Breslow (Columbia University) and Dr. Paul Anderson (Dupont-Merck Pharmaceutical Company)
Back Row (left to right): Ron Pongdee, Sam Brown, Justin Hasford, Jason Buck, Dan Prudhomme, Carmelo Rizzo
Front Row (left to right): Minnie Park, Ronald Breslow, Sharon Parker, Paul Anderson
Publications of C. J. Rizzo
Independent Work:
"Stereospecific Formation of Interstrand Carbinolamine DNA Crosslinks by Crotonaldehyde- and Acetaldehyde-Derived ±-CH3-&Mac179;-OH-1,N2-Propano-2'-deoxyguanosine Adducts in the 5'-CpG-3' Sequence." Young-Jin Cho, Hao Wang, Ivan D. Kozekov, Andrew J. Kurtz, Jaison Jacob, Markus Voehler, Jarrod Smith, Thomas M. Harris, R. Stephen Lloyd, Carmelo J. Rizzo, and Michael P. Stone, Chemical Research in Toxicology, 2006, 19, (in press)
"Monitoring the Acrolein &Mac179;-OH-PdG DNA Adduct in situ Using 13C NMR: Formation of a Carbinolamine Interstrand Crosslink in 5'-CpG-3' Sequence Context." Young-Jin Cho, Hye-Young Kim, Hai Huang, Alvira Slutsky, Irina G. Minko, Hao Wang, Lubomir V. Nechev, Ivan D. Kozekov, Albena Kozekova, Pamela Tamura, Jaison Jacob, Markus Voehler, Thomas M. Harris, R. Stephen Lloyd, Carmelo J. Rizzo, and Michael P. Stone, J. Am. Chem. Soc. 2005, 127, 17686-17696
"Site-Specific Synthesis and Polymerase Bypass of Oligonucleotides Containing a 6-Hydroxy-3,5,6,7-tetrahydro-9H-imidazo[1,2-a]purin-9-one base. An Intermediate in the Formation of 1,N2-Etheno-2'-deoxyguanosine." Angela K. Goodenough, Ivan D. Kozekov, Hong Zang, Jeong-Yun Choi, F. Peter Guengerich, Thomas M. Harris and Carmelo J. Rizzo, Chemical Research in Toxicology, 2005, 18, 1701-1714.
"DNA Adduct Bypass Polymerization By Sulfolobus Solfataricus DNA Polymerase Dpo4: Analysis and Crystal Structures of Multiple Base-Pair Substitution and Frameshift Products with the Adduct 1,N2-Ethenoguanine." Hong Zang, Angela K. Goodenough, Jeong-Yun Choi, Adriana Irimia, Lioudmila V. Loukachevitch, Ivan D. Kozekov, Karen C. Angel, Carmelo J. Rizzo, Martin Egli, and F. Peter Guengerich, Journal of Biological Chemistry 2005, 280, 29750-29764.
"Structure of an Oligodeoxynucleotide Containing a Butadiene Oxide-Derived N1 Beta-Hydroxyalkyl Deoxyinosine Adduct in the Human N-ras Codon 61 Sequence." Tandy A. Scholdberg, W. Keither Merritt, Stephen M. Dean, Agnieska Kowalcyzk, Constance M. Harris, Thomas M. Harris, Carmelo J. Rizzo, R. Stephen Lloyd, Michael P. Stone, Biochemistry 2005, 44, 3327-3337.
"Synthesis of the N2-Deoxyguanosine Adduct of the Potent Dietary Mutagen IQ." James S. Stover and Carmelo J. Rizzo, Organic Letters 2004, 6, 4985-4988.
"Site-Specific Synthesis and Properties of Oligonucleotides Containing C8-Deoxyguanosine Adducts of the Dietary Mutagen IQ." C. Eric Elmquist, James S. Stover, Zhiwei Wang and Carmelo J. Rizzo, Journal of the American Chemical Society 2004, 126, 11189-11201.
"Coupling Products of Nucleosides with the Glyoxal Adduct of Deoxyguanosine" Angela K. Brock, Ivan D. Kozekov, Carmelo J. Rizzo, and Thomas M. Harris, Chemical Research in Toxicology 2004, 17, 1047-1056.
"Induction of Apoptosis in Colorectal Carcinoma Cells
Treated with 4-Hydroxy-2-nonenal and Structurally Related Aldehydic
Products of Lipid Peroxidation." James D. West, Chuan Ji,
Stephen T. Duncan, Venkataraman Amarnath, Claus Schneider, Carmelo
J. Rizzo, Alan R. Brash, and Lawrence J. Marnett, Chemical
Research in Toxicology 2004, 17, 453-462.
"A Novel Synthesis of Malondialdehyde Adducts of Deoxyguanosine,
Deoxyadenosine and Deoxycytidine." Hao Wang, Lawrence J.
Marnett, Thomas M. Harris and Carmelo J. Rizzo, Chemical Research
in Toxicology 2004, 17, 144-149.
"Stereoselective Synthesis of the 1,N2-Deoxyguanosine Adducts of Cinnamaldehyde. A Stereocontrolled Route to Deoxyguanosine Adducts of ±,<-Unsaturated Aldehydes. " Mansoureh Rezaei, Thomas M. Harris, Carmelo J. Rizzo, Tetrahedron Letters, 2003, 44, 7513-7516.
"Site-Specific Mutagenicity of Stereochemically Defined 1,N2-Deoxyguanosine Adducts of 4-Hydroxynonenal in Mammalian Cells." Priscilla H. Fernandes, Hao Wang, Carmelo J. Rizzo and R. Stephen Lloyd, Environmental and Molecular Mutagenesis, 2003, 42, 68-74.
"Site-Specific Synthesis and Reactivity of Oligonucleotides Containing Stereochemically Defined 1,N2-Deoxyguanosine Adducts of the Lipid Peroxidation Product trans-4-Hydroxynonenal" Hao Wang, Ivan D. Kozekov, Thomas M. Harris and Carmelo J. Rizzo, Journal of the American Chemical Society 2003, 125, 5687-5700.
"DNA Interchain Cross-links Formed by Acrolein and Crotonaldehyde." Ivan D. Kozekov, Lubomir V. Nechev, M. Scott Moseley, Constance M. Harris, Carmelo J. Rizzo, Michael P. Stone and Thomas M. Harris, Journal of the American Chemical Society 2003, 125, 50-61.
"DNA Adducts of Acolein: Site-specific Synthesis of an Oligonucleotide Containing 6-Hydroxy-5,6,7,8-tetrahydropyrimido[a,2-a]purin-10(3H)-one, an Acolein adduct of Guanine." Lubo V. Neechev, Angela K. Brock, Carmelo J. Rizzo, Thomas M. Harris, Chemical Research in Toxicology, 2002, 15, 607.
"An N1-Hydrogen Bonding Model for Flavin Coenzyme." Fengli Guo , Bryan H. Chang and Carmelo J. Rizzo, Bioorganic and Medicinal Chemistry Letters 2002, 12, 151-154.
"Stereocontrolled Syntheses of All Four Stereoisomeric 1,N2-Deoxyguanosine Adducts of the Lipid Peroxidation Product trans-4-Hydroxynonenal." Hao, Wang, Carmelo J. Rizzo, Organic Letters, 2001, 3, 3603.
"An N1-Hydrogen Bonding Model for Flavin Coenzyme." Fengli Guo, Bryan H. Chang and Carmelo J. Rizzo , Bioorganic and Medicinal Chemistry Letters, 2001, 11, 151.
"Further Computational Studies on 1,5-Dihydrolumiflavin." C. J. Rizzo, Antioxidants and Redox Signaling, 2001 3, 737-745
"Absolute Configuration and Conformational Stability of (+)-2,5-Dimethylthiolane and (-)-2,5-Dimethylsulfolane." Feng Wang, Hao Wang, Prasad Polavarapu and Carmelo J. Rizzo, Journal of Organic Chemistry, 2001, 66 , 3507-3512.
"Synthesis of the C8-Deoxyguanosine Adduct of the Food Mutagen IQ." Zhiwei Wang and Carmelo J. Rizzo, Organic Letters, 2001, 3, 565.
"Absolute Configuration, Predominant Conformation and Vibrational Circular Dichroism Spectra of Enantiomers of n-Butyl t-Butyl Sulfoxide." Jozef Drabowicz, Bogdan, Dudzinski, Marian Mikolajczyk, Feng Wang, Afshan Dehlavi, Joann Goring, Minnie Parkm Carmelo J. Rizzo, Prasad L. Polavarapu, Paolo Biscarini, Michael W. Wieczorek and Wieslaw R. Majzner Journal of Organic Chemistry, 2001, 66, 1122.
"Stereocontrolled Synthesis of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl Protected Ribo- and Arabinonucleosides." Zhiwei Wang, Daniel R. Prudhomme, Jason R. Buck, Minnie Park and Carmelo J. Rizzo, Journal of Organic Chemistry 2000, 65, 5969.
"Regioselective Synthesis of beta-N1 and beta N3-Alloxazine Nucleosides." Zhiwei Wang, Carmelo J. Rizzo, Organic Letters 2000, 2 , 227.
"X-Ray Crystal Structures of Conformationally Biased Flavin Models." Joseph H. Reibenspies, Fengli Guo and Carmelo J. Rizzo Organic Letters 2000, 2 , 903.
"Synthesis of 2'-Deoxyribonucleosides: beta-3',5'-Di-O-benzoylthymidine." Daniel R. Prudhomme, Minnie Park, Zhiwei Wang, Jason R. Buck and Carmelo J. Rizzo, Organic Syntheses 1999, 77, 162.
"3,6-Dimethyl-9-ethylcarbazole (DMECZ)." Jason R. Buck, Minnie Park, Zhiwei Wang, Daniel R. Prudhomme and Carmelo J. Rizzo, Organic Syntheses, 1999, 77, 153.
"A Convenient Synthesis of 3,6-Substituted Carbazoles via Nickel Catalyzed Cross-Coupling." Minnie Park, Jason R. Buck and Carmelo J. Rizzo, Tetrahedron 1998, 54, 12707.
"Linear Free Energy Substituent Effect on Flavin Redox Chemistry." Justin J. Hasford and Carmelo J. Rizzo, Journal of the American Chemical Society, 1998, 120, 2251.
"Reduction of Hg(II)-EDTA by Conformationally Biased Flavin." Justin J. Hasford and Carmelo J. Rizzo, Tetrahedron Letters, 1998, 39, 1317.
"Stereocontrolled Synthesis of alpha-2 '-Deoxyribonucleosides," Zhiwei Wang and Carmelo J. Rizzo, Tetrahedron Letters, 1997, 38 , 8177.
"An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and m-(Trifluoromethyl)benzoates." Daniel R. Prudhomme, Zhiwei Wang and Carmelo J. Rizzo, Journal of Organic Chemistry 1997, 62 , 8257.
"Conformational Effects on Flavin Redox Chemistry." Justin J. Hasford, William Kemnitzer and Carmelo J. Rizzo, Journal of Organic Chemistry 1997, 62 , 5244.
"A 'One-Pot' Alkylation/Hydrolysis of o-Nitrotrifluoroacetanilides. A Convenient Route to N-Alkyl o-Phenylenediamines." Samuel A. Brown and Carmelo J. Rizzo, Synthetic Communications 1996, 26 , 4065.
"Stereocontrolled, De Novo Synthesis of beta-2 '-Deoxyribonucleosides." Minnie Park and Carmelo J. Rizzo, Journal of Organic Chemistry 1996, 61 , 6092.
"Facile Addition of Dichloroketene to Acetylenes Mediated by Zinc and Ultrasound." M. Sharon A. Parker and Carmelo J. Rizzo, Synthetic Communications 1995, 25 , 2781-9.
"Salt Effects in a Hydrophobically Accelerated Diels-Alder Reaction Follows the Hofmeister Series." Carmelo J. Rizzo, Journal of Organic Chemistry, 1992, 57 , 6382-4.
From Graduate and Post-doctoral Work:
"(+)-Trienomycins A, B, C and F and (+)-Mycotrienins I and II: Relative and Absolute Stereochemistry." Amos B. Smith, III, John L. Wood, Weichyun Wong, Alexandra E. Gould, Carmelo J. Rizzo, Joseph Barbosa, Shinji Funayama, Kanki Komiyama and Saatoshi Omura, Journal of the American Chemical Society 1996, 118 , 8308.
"(+)-Hitachimycin: Stereochemistry and Conformational Analysis." Amos B. Smith, III, John L. Wood, Carmelo J. Rizzo, George T. Furst and Patrick J. Carroll and Jerry Donohue, Journal of the American Chemical Society, 1992, 114 , 8003-7.
"Oligodeoxynucleotides That Contain 2 ',5 ''-Linkages: Synthesis and Hybridization Properties." Joseph P. Dougherty, Carmelo J. Rizzo and Ronald Breslow, Journal of the American Chemical Society 1992, 114 , 6254-5.
"3 '-Deoxy-2 '-Phosporamidites of Adenosine and 5-Methyluridine Used for the Solid Phase Synthesis of Unnatural 3 '-Deoxy-2 ',5 ''-Oligonucleotides." Carmelo J. Rizzo, Joseph P. Dougherty and Ronald Breslow, Tetrahedron Letters 1992, 33 , 4129-33.
"Chaotropic Salt Effects in a Hydrophobically Accelerated Diels-Alder Reaction." Ronald Breslow and Carmelo J. Rizzo, Journal of the American Chemical Society, 1991, 113 , 4340-1.
"Aphidicolin Synthetic Studies: A Stereocontrolled End Game." Carmelo J. Rizzo and Amos B. Smith, III, Journal of the Chemical Society, Perkin Transaction I 1991, 969-79.
"(+)-Trienomycins A, B, and C: Relative and Absolute Stereochemistry." Amos B. Smith, III, John L. Wood, Weichyun Wong, Alexandra E. Gould, Carmelo J. Rizzo, Shinji Funayama and Satoshi Omura, Journal of the American Chemical Society, 1990, 112 , 7425-6.
"Aphidicolin Synthetic Studies, 2. 2D-NMR Analysis of (+)-Aphidicolin and Its Degradation Products 3a,18-Dihydroxy-17-noraphidicolan-16-one and 3a,18-Isopropylidenedioxy-17- noraphidicolan-16-one. Complete 1H and 13C Assignments." Carmelo J. Rizzo, John L. Wood, George T. Furst and Amos B. Smith, III, Journal of Natural Products, 1990, 53 , 735-9.
"Solution and Crystal Structures of (+)-Hitachimycin (Stubomycin)." Amos B. Smith, III, John L. Wood, Carmelo J. Rizzo, George T. Furst and Patrick J. Carroll, Jerry Donohue and Satoshi Omura, Journal of Organic Chemistry, 1990 55 , 1133-5.
"A New End Game for Aphidicolin." Carmelo J. Rizzo and Amos B. Smith, III, Tetrahedron Letters, 1988, 29 , 2793-6.
"A Convenient Preparation of 4- and 5-Substituted Cyclopentenones: A Short Synthesis of Methylenomycin B." Carmelo J. Rizzo, Norma K. Dunlap and Amos B. Smith, III, Journal of Organic Chemistry, 1987, 52 , 5280-3.
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