Dr. John Spence 

John Spence



Education

BS Chemistry, Saint Mary’s College of California, 1992

Ph D Chemistry, University of California, Davis, 1997

Office:  SQU 538C

Phone: (916) 278-4477

Email: jspence@csus.edu







Home page

http://www.csus.edu/indiv/s/spencej/

Courses

Chem 24, 124 – Organic Chemistry I and II Lecture
Chem 25 – Organic Chemistry Laboratory
Chem 125 – Advanced Organic Chemistry Laboratory
Chem 128 – Organic Synthesis
Chem 240 – Advanced Instrumentation Laboratory

Research:

Research in my group is centered around two general areas in synthetic organic chemistry: (1) the synthesis and activation of enediyne pro-drugs and (2) the synthesis and properties of macrocycles related to porphyrins and calixarenes.

The Bergman cyclization of enediynes to produce 1,4-phenyl diradicals is an attractive mode of action to cleave DNA. This cyclization may be initiated thermally or photochemically to produce a benzenoid diradical which is followed by hydrogen atom abstraction from the sugar backbone of DNA leading to strand scission and cell death. We are currently developing enediyne pro-drugs that are fused to heteroaromatic ring systems including porphyrins to improve DNA binding. In addition, we are exploring methods to improve photochemical activation of the enediyne unit by extending conjugation to the enediyne chromophore.

We are also interested in fine-tuning the properties of calixarenes by developing synthetic methods to systematically replace the bridging carbon atoms in these macrocycles with nitrogen atoms. This substitution can have a profound effect on the electronic and physical properties of these macrocycles and offer new motifs for their functionalization.

Recent Publications and Presentations:

Publications

 J. D. Spence, M. L. Lackie, N. A. Clayton, S. A. Toscano, M. A. Farmer, E. Popova, M. M. Olmstead.  Syntheses, Structure, and Reactivity of Acyclic Enetriyne and Enetetrayne Derivatives.  Tetrahedron Letters, 2014, 55, 1569-1572.

J. D. Spence, A. C. Rios, M. A. Frost, C. M. McCutcheon, C. D. Cox, S. Chavez, R. Fernandez, B. F. Gherman.  Syntheses, Thermal Reactivities and Computational Studies of Aryl-Fused Quinoxalenediynes:  Effect of Extended Benzannelation on Bergman Cyclization Energetics.  Journal of Organic Chemistry, 2012, 77, 10329-10339.

N. V. Korovina, M. L. Chang, T. T. Nguyen, R. Fernandez, H. J. Walker, M. M. Olmstead, B. F. Gherman and J. D. Spence.  Syntheses and Reactivity of Naphthalenyl-Substituted Arenediynes.  Organic Letters, 2011, 13, 3660-3663.

K. V. Lawson, A. C. Barton and J. D. Spence.  Synthesis of Diazacalix[8]arene and Triazacalix[12]arene Methyl Ethers via Intramolecular Aryl Amination.  Organic Letters, 2009, 11, 895-898.
 
A. R. Urbach, C. J. Pursell and J. D. Spence.  Supramolecular Chemistry:  A Senior Capstone Course.  J. Chem. Ed., 2007, 84, 1785-1787.
 
J. D. Spence, A. E. Hargrove, H. L. Crampton and D. W. Thomas.  Porphyrenediynes:  Synthesis and Cyclization of meso-Enediynylporphyrins.  Tetrahedron Letters, 2007, 48, 725-728.

Presentations

Adam B. Ung, Benjamin F. Gherman and John D. Spence.  "Computational Study of the Cyclization Reactions of Phenyl-Substituted Enediynes with Benzannelated and Quinoxaline-Based Supporting Groups."  Presented at the 26th Annual Northern California ACS Undergraduate Research Symposium, University of San Francisco, May 2014.

Kiara Velazquez, Elizabeth Grace Tuazon and John D. Spence.  "Steric and Electronic Effects on Photochemical Bergman Cyclization of Acyclic Enediynes."  Presented at the 26th Annual Northern California ACS Undergraduate Research Symposium, University of San Francisco, May 2014.

Anthony W. Vuong and John D. Spence.  "Examining Aromaticity Gain in the Bergman Cyclization of Quinoxalenediynes."  Presented at the 26th Annual Northern California ACS Undergraduate Research Symposium, University of San Francisco, May 2014.

Phillip J. Marzouk, Benjamin F. Gherman and John D. Spence.  "Time Dependent Density Functional Theory Study of the Bergman Photocyclization Reactivity of Enediynes."  Presented at the 26th California State University Biotechnology Symposium, Santa Clara, CA, January 2014.

Cui Q. Li, Benjamin F. Gherman and John D. Spence.  "Computational and Experimental Study of the Thermal Cyclization of Enediynones and Dienyynones."  Presented at the 26th California State University Biotechnology Symposium, Santa Clara, CA, January 2014.

Kiara Velazquez and John D. Spence.  "Enhanced photo-Bergman cyclization of an electron rich mono-substituted arenediyne."  Presented at the CSUS NSM Undergraduate Research Reception, October, 2013.

Sergio A. Toscano and John D. Spence.  "Design and synthetic approach towards novel quinoxalenediynes."  Presented at the CSUS NSM Undergraduate Research Reception, October, 2013.

Phillip J. Marzouk, Benjamin F. Gherman and John D. Spence.  "Photoexcitation of Enediyne Compounds and Implications for their Bergman Cyclization Reactivity."  Presented at the 44th Western Regional American Chemical Society Meeting, Santa Clara, CA, October 2013.  Paper 51.

Cui Q. Li, Benjamin F. Gherman and John D. Spence.  "Computational and Experimental Study of the Thermal Cyclization of Enediynones and Dieneynones."  Presented at the 44th Western Regional American Chemical Society Meeting, Santa Clara, CA, October 2013.  Paper 50.

Sergio A. Toscano and John D. Spence.  "Design and synthetic approach towards novel quinoxalenediynes."  Presented at the 44th Western Regional American Chemical Society Meeting, Santa Clara, CA, October 2013.  Paper 330.

Kiara Velazquez and John D. Spence.  "Enhanced photo-Bergman cyclization of an electron rich mono-substituted arenediyne."  Presented at the 44th Western Regional American Chemical Society Meeting, Santa Clara, CA, October 2013.  Paper 329.

Esfir Popova and John D. Spence.  "Electronic Properties and Photo-Reactivity of Highly Conjugated Enediynes."  Presented at the 25th Annual Northern California ACS Undergraduate Research Symposium, Santa Clara University, May 2013.

Mofeid Y. Hussain and John D. Spence.  "Enhanced Photo-Bergman Cyclization of a Methoxy Substituted Arenediyne."  Presented at the 25th Annual Northern California ACS Undergraduate Research Symposium, Santa Clara University, May 2013.

Kiara Velazquez and John D. Spence.  "Synthesis and Reactivity of Electron Rich Enediynes."  Presented at the 25th Annual Northern California ACS Undergraduate Research Symposium, Santa Clara University, May 2013.

Brianna White and John D. Spence.  "Synthesis of Imidazol-5-yl Substituted Arenediyne to Examine Photo-Bergman Cyclization."  Presented at the 25th Annual Northern California ACS Undergraduate Research Symposium, Santa Clara University, May 2013.

Kellie Minnick, Ramiro P. Fernandez, Benjamin F. Gherman and John D. Spence. “Computational Analysis of Cyclization Reactions of Monosubstituted Enediynes and Comparison to Disubstituted Enediynes.”  Presented at the 25th California State University Biotechnology Symposium, Anaheim, CA, January 2013.

Phillip J. Marzouk, Benjamin F. Gherman and John D. Spence. “Photoactivation of Enediyne Compounds and Implications for Their Bergman Cyclization Reactivity.”  Presented at the 25th California State University Biotechnology Symposium, Anaheim, CA, January 2013.

Nadia Korovina, Benjamin F. Gherman and John D. Spence.  "Synthesis and Photoreactivity of 1,2-bis(naphthalene-1-ylethynyl)benzene:  A Combined Experimental and Computational Investigation."  Presented at the 238th National Meeting of the American Chemical Society, Washington D. C., August 2009.  Paper CHED 283.
 
Michael L. Chang and John D. Spence.  "Syntheses and Reactivity of (Naphthalen-2-yl) and (Phenanthren-9-yl)ethynyl Arenediynes."  Presented at the 237th National Meeting of the American Chemical Society, Salt Lake City, UT, April 2009.  Paper CHED 863.
 
Joseph R. Renner and John D. Spence.  "Highly Conjugated Arenediynes:  Synthesis, Structure, and Reactivity of 1,2-bis(2-(Anthracen-9-yl)ethynyl)benzene."  Presented at the 237th National Meeting of the American Chemical Society, Salt Lake City, UT, April 2009.             Paper CHED 775.
 
Kristie A. Rivera and John D. Spence.  "Synthesis of Phenanthro-Fused Quinoxalenediynes to Examine Enediyne Photoreactivity with Visible Light."  Presented at the 235st National Meeting of the American Chemical Society, New Orleans, LA, April 2008.  Paper 494.
 
Heather J. Walker and John D. Spence.  "Synthesis and Photo-Bergman Cyclization of Naphthylethynyl Arenediynes."  Presented at the 235st National Meeting of the American Chemical Society, New Orleans, LA, April 2008.  Paper 363.

J. D. Spence.  “Synthesis and Bergman Cyclization of Highly Conjugated Arenediynes.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 17.

Andro C. Rios and John D. Spence.  “Design and Synthesis of Aryl-Fused Quinoxalenediynes.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 373.

Kenneth V. Lawson and John D. Spence.  “Synthetic Approaches Towards mono-Azacalix[4]arene.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 551.

Miranda L. Lackie and John. D. Spence.  “Synthesis of 1,2-Bis(phenylbutadiynyl)benzene.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 519.

.