The Department of Natural Sciences
Edyta Greer, Ph.D.
Associate Professor of Computational Chemistry
Phone: (646) 660-6220
Ph.D.: Graduate Center, CUNY
Postdoctoral Research: Cornell University
Current Research Interests:
Research in my group focuses on theoretical and experimental approaches to novel enediyne drugs that undergo the Bergman cyclization to kill cancerous cells. For example, we conduct quantum mechanical calculations to analyze replacement of a carbon fragment with a metal fragment in organic molecules (by means of the isolobal analogy) to “perturb” the energetic of the Bergman cyclization. Such perturbation methods may have interesting implications for Cope and Diels-Alder reactions too. We also study tropolone molecules, such as the material found in Thuja trees, which exhibit wide but “untamed” cytotoxic properties. Our synthetic chemistry is targeting the generation of new tropolone compounds with better selective inhibition of the metalloenzyme, HIV-1 integrase. My group also has two active collaborations; one involving synthetic and mechanistic studies of 1-benzazepine compounds with Prof. Ramig, and the other analyzing natural materials from marine organisms isolated by Prof. Gruber.
The Petroleum Research Fund of the American Chemical Society Grant No. 54244-UR4 (2014-2017)
(*Baruch undergraduate student)
Keith Ramig, Gopal Subramaniam, Sasan Karimi, David J. Szalda, Allen Ko,* Aaron Lam,* Jeffrey Li,* Ani Coaderaj,* Leyla Cavdar,* Lukasz Bogdan,* Kitae Kwon,* Edyta M. Greer “Interplay of Nitrogen-Atom Inversion and Conformational Inversion in Enantiomerization of 1H-1-Benzazepines” Journal of the Organic Chemistry, 2016, DOI:10.1021/acs.joc.6b00319.
Sasan Karimi, Shuai Ma, Keith Ramig, Edyta M. Greer, David J. Szalda, Gopal Subramaniam “Oxidative Ring-contraction of 3H-1-Benzazepines to Quinoline Derivatives” Tetrahedron Letters 2015, 56, 6886-6889.
Marilene Silva Oliveira, Ashwini A. Ghogare, Inna Abramova, Edyta M. Greer, Fernanda Manso Prado, Paolo Di Mascio, Alexander Greer “Mechanism of Photochemical O-Atom Exchange in Nitrosamines with Molecular Oxygen” Journal of the Organic Chemistry, 2015, 80, 6119-6127.
Edyta M. Greer, Cesar S. Quezada,* Christopher V. Cosgriff* “Butylated Hydroxytoluene Enediyne: Access to Diradical and Electrophilic Quinone Methide Intermediates” Journal of Physical Organic Chemistry, 2015, 28, 365-369.
Allen Ko,* Aaron Lam,* Jeffrey Li,* Edyta M. Greer, David J. Szalda, Sasan Karimi, Gopal Subramaniam, Keith Ramig “Regioselective Alkylation Reactions of 2,4-Diphenyl-3H-1-benzazepine Give Either 3-alkyl-3H-1-benzazepines or 1-alkyl-1H-1-benzazepines” Tetrahedron Letters, 2014, 55, 4386-4389.
Edyta M. Greer, Christopher V. Cosgriff,* Charles Doubleday “Computational Evidence for Heavy-Atom Tunneling in the Bergman Cyclization of a 10-Membered-Ring Enediyne” Journal of the American Chemical Society, 2013, 135, 10194-10197. (highlighted on the website of JACS and by Computational Chemistry Highlights (http://www.compchemhighlights.org/2013/07/tunneling-in-bergman-cyclization.html))
Edyta M. Greer, Christopher V. Cosgriff* “Reaction Mechanisms: Pericyclic Reactions” Annual Reports Section “B” (Organic Chemistry), 2013, 109, 328-350.
Keith Ramig, Edyta M. Greer, David J. Szalda, Sasan Karimi, Allen Ko,* Laura Boulos,* Jiansan Gu,* Nathan Dvorkin,* Hema Bhramdat, Gopal Subramaniam, “NMR Spectroscopic and Computational Study of Conformational Isomerism in Substituted 2-Aryl-3H-1-benzazepines: Toward Isolable Atropisomeric Benzazepine Enantiomers” Journal of the Organic Chemistry, 2013, 78, 8028-8036.
Sasan Karimi, Keith Ramig, Edyta M. Greer, David J. Szalda, William F. Berkowitz, Prakash Prasad, Gopal Subramaniam, “Tandem Ring-Contraction/Decarbonylation of 2,4-Diphenyl-3H-1-benzazepine to 2,4-Diphenylquinoline” Tetrahedron 2013, 69, 147-151.
Edyta M. Greer, Christopher V. Cosgriff,* Olga Lavinda* “A Curtin-Hammett Pentamethylene Chain Symmetrization Process in the Bergman Cyclization of an 11-Membered-Ring Enediyne” Journal of Physical Organic Chemistry, 2012, 25, 1293–1298.
Edyta M. Greer, Christopher V. Cosgriff* “Reaction Mechanisms: Pericyclic Reactions” Annual Reports Section “B” (Organic Chemistry), 2012, 108, 251-271.
Edyta M. Greer, Mariya Tolmachova “Marie Curie: Pioneering Discoveries and Humanitarianism” Helvetica Chimica Acta, 2011, 94, 1893-1907. (featured in CUNY Research Newsletter 2012, 7, 8)
Edyta M. Greer, Olga Lavinda* “Theoretical Study of the Bergman cyclization of 2,3-Diethynyl-1-nitrotropylium Ion: Formation of a Nitroxide Radical Amenable to EPR Detection for Biological Applications” Journal of Organic Chemistry, 2010, 75, 8650-8653.
Keith Ramig, Edyta M. Greer, David J. Szalda, Rabail Razi,* Fahima Mahir,* Nataliya Pokeza,* Wei Wong,* Benjamin Kaplan,* Joanne Lam,* Ayesha Mannan,* Christopher Missak,* Dat Mai,* Gopal Subramaniam, William F. Berkowitz, Prakash Prasad, Sasan Karimi, Ngai Hin Lo, and Linas V. Kudzma “Experimental and Theoretical Studies of a One-flask Synthesis of 3H-1-Benzazepines from 2-Haloanilines and alpha,beta-Unsaturated Ketones” The European Journal of Organic Chemistry, 2010, 2363-2371.
Edyta M. Greer, Roald Hoffmann “Metalla-Cope Rearrangements: Bridging Organic and Inorganic Chemistry” Journal of Physical Chemistry A, 2010, 26, 2248-2255. (highlighted on the front page of the website of the American Chemical Society, and it was the second most accessed paper in the first three months of 2010 for the JPChem A)
Edyta M. Greer, David J. Aebisher, Alexander Greer, Ronald Bentley “Computational Studies of the Tropone Natural Products, Thiotropocin, Tropodithietic Acis, and Troposulfenin. Significance of Keto-Thiol Tautomerism” Journal of Organic Chemistry, 2008, 73, 280-283.
Edyta M. Brzostowska, Roald Hoffmann, Carol A. Parish “Tuning the Bergman Cyclization by Introduction of Metal Fragments at Various Positions of the Enediyne. MetallaBergman Cyclizations” Journal of the American Chemical Society, 2007, 129, 4401-4409.
Aaron T. Frank, Nicola S. Farina, Nahed Sawwan, Mo Qi, Edyta M. Brzostowska, Frank W. Grasso, Paul Haberfield, Alexander Greer “Natural Macromolecules Have a Limited Structural Diversity?” Molecular Diversity 2007, 11, 115-118.
David J. Aebisher, Edyta M. Brzostowska, Nahed Sawwan, Rafeal Ovalle, Alexander Greer “Implication for the Existence of a Heptasulfur Linkage in Natural o-Benzopolysulfanes” Journal of Natural Products, 2007, 70, 1492-1494.
Edyta M. Brzostowska, Martine Paulynice, Ronald Bentley, Alexander Greer “Planar Chirality Due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity” Chemical Research in Toxicology, 2007, 20, 1046-1052.
David J. Aebisher, Edyta M. Brzostowska, Mahendran Adaickpillai, Alexander Greer “Regioselective (Biomimetic) Synthesis of a Pentasulfane from ortho-Benzoquinone” Journal of Organic Chemistry, 2007, 72, 2951-2955.
Nahed Sawwan, Edyta M. Brzostowska, Alexander Greer “Substituent Effects on the Reactivity of Benzo-1,2-dithiolan-3-one 1-Oxides and Their Possible Application to the Synthesis of DNA-Targeting Drugs” Journal of Organic Chemistry, 2005, 70, 6968-6971.
Edyta M. Brzostowska, Alexander Greer “Polysulfane Antitumor Agents from o-Benzyne. An Odd-Even Alternation Found in the Stability of Products o-C6H4Sx (x=1-8)” Journal of Organic Chemistry, 2004, 69, 5483-5485.
Edyta M. Brzostowska, Alexander Greer “The Role of Amine in the Mechanism of Pentathiepin (Polysulfur) Antitumor Agents” Journal of the American Chemical Society, 2003, 125, 396-404.
(name appears as Edyta M. Brzostowska before 2008)
The Greer Research Group
Current Group Members (Quants):
Kitae Kwon (undergraduate student - Aug. 2014 – present)
Christopher V. Cosgriff (research assistant - May 2013 – present)
Former Group Members:
14. Anastasia Badziai (Sept. 2015 – Dec. 2015)
13. Elena Votto (Feb. 2015 – Aug. 2015)
12. Jade Marino Creto (Aug. 2014 – June 2015)
11. Lukasz Bogdan (Sept. 2013 – June 2014)
10. John Ortiz (Sept. 2013 – Dec. 2013)
9. Cesar Quezada (Sept. 2012 – May 2013)
8. Michael Erdos (Sept. 2012 – Dec. 2012)
7. Irina Kushenazarova (Jan. 2011 – May 2012)
6. Christopher V. Cosgriff (Jan. 2011 – May 2013)
5. Nathan Dvorkin (Sept. 2010 – Aug. 2012)
4. Janna Petrovich (Jan. 2010 – May 2011)
3. Dat Mai (Jan. 2009 – Dec. 2010)
2. Rose Connor (Sept. 2008 – Dec. 2008)
1. Olga Lavinda (Sept. 2008 – Jan. 2011)