Alexander Greer

  Professor
  Department: Chemistry
  Location: 341 Ingersoll Hall Extension
  Phone: 718-951-5000 x2830
  Fax: 718-951-4607

  Email:

Our group is interested in fundamental aspects of organic chemistry. Factors that control reactions of oxygen and sulfur species are of interest. We are involved in research of atomic oxygen, singlet molecular oxygen, and other reactive and cytotoxic agents. Some molecules used in our studies (polysulfanes) exhibit cytotoxic properties that must have taken eons to evolve, formed by marine invertebrates to deter predators. Our synthetic chemistry aims to create polysulfanes with increased anti-tumor activity over those found in Nature. Using chemicals synthesized with functionality to initiate cell responses or the modulation of specific cell sensitivity is of interest. Computations are used to try to deepen our understanding of experiments. We often probe organic mechanisms with ab initio and density functional theory.

Education:
Postdoctoral Fellow, UCLA - 1999 (Organic Chemistry)

Doctor of Philosophy, University of Wyoming - 1996 (Organic Chemistry)

Areas of Expertise:
physical organic chemistry; photooxidation mechanisms; singlet oxygen; preparative-, theoretical-, and photochemistry; molecular mechanisms of toxicity; enantiospecific toxicity; antitumor and antifungal compounds; natural products; organism chemical defense mechanisms; natural selection of biological agents; chemical evolution.

Doctoral Rotation Projects:
Techniques to be learned upon doing lab rotations may include: Methods in Photochemistry, Organic Synthesis, and Drug Design; Nuclear Magnetic Resonance and Liquid Chromatography-Mass Spectrometry (LC/MS) Techniques, Laser Spectroscopy, and Computational Theory.

Books and Publications
A. Castillo, A. Greer "Theoretical Studies of a Singlet Oxygen-Releasing Dioxapaddlane (1,4-Diicosa naphthalene-1,4-endoperoxide)." Struct. Chem., 20, 399-407.
(Books and Publications: Forthcoming Publications) 2009

M. L. Raber; A. Castillo; A. Greer; C. A. Townsend "A Conserved Lysine in b-Lactam Synthetase Assists Ring Cyclization: Implications for Clavam and Carbapenem Biosynthesis" ChemBioChem (submitted). (Books and Publications: Peer Reviewed Article) 2009

Zamadar, M.; Aebisher, D.; Greer, A. "Singlet Oxygen Delivery Though the Porous Cap of a Hollow-Core Fiber Optic Device" J. Phys. Chem. B (submitted). (Books and Publications: Forthcoming Publications) 2009

Zamadar, M.; Greer, A. "Singlet Oxygen as an Reagent in Organic Synthesis" In Handbook of Synthetic Photochemistry; Albini, A., Ed.; Wiley-VCH: Weinheim (in press). (Books and Publications: Peer Reviewed Article) 2009

A. Greer, D. Aebisher; Editors. Special Issue: "Extreme Sulfur Chemistry" [In: Journal of Sulfur Chemistry, 29, 241-457]. (Books and Publications: Peer Reviewed Article) 2008

A. Castillo, J. F. Liebman; A. Greer "Quinones, Monoradicals and Diradicals From 3- and 4-Mercaptocatechol, and 3,4-Bismercaptocatechol: A Computational Study of a Plausibly Biomimetic Reaction," J. Sulfur Chem., 29, 445-457. (Books and Publications: Peer Reviewed Article) 2008

A. Greer and J. F. Liebman "Paradigms and Paradoxes: Energetics of the Oxidative Cleavage of Azo Compounds," Struct. Chem., 19, 817-818. (Books and Publications: Peer Reviewed Article) 2008

D. Aebisher, A. Greer; preface. "Extreme Sulfur Chemistry" [In: J. Sulfur Chem. 2008; 29, 241-241]. (Books and Publications: Peer Reviewed Article) 2008

D. Aebisher; N. S. Azar, M. Zamadar; H. D. Gafney; N. Gandra; R. Gao, A. Greer "Singlet Oxygen Chemistry in Water. A Porous Vycor Glass--Supported Photosensitizer," J. Phys. Chem. B, 112, 1913-1917. (Books and Publications: Peer Reviewed Article) 2008

E. M. Greer; D. Aebisher; A. Greer; R. Bentley "Computational Studies of the Tropone Natural Products, Thiotropocin, Tropodithietic acid, and Troposulfenin. Significance of Thiocarbonyl-enol Tautomerism" J. Org. Chem., 73, 280-283. (Books and Publications: Peer Reviewed Article) 2008

J. Giaimuccio, M. Zamadar, D. Aebisher, G. J. Meyer, A. Greer "Singlet Oxygen Chemistry in Water. 2. Photophysics of Quenching of a Photosensitizer by O2 at the Water/Porous Glass Interface." J. Phys. Chem. B, 112, 15646-15650. (Books and Publications: Peer Reviewed Article) 2008

A. Greer "Organic Chemistry: Molecular Crosstalk," Nature, 447, 273-274. (Books and Publications: Peer Reviewed Article) 2007

A. T. Frank; A. Adenike; D. Aebisher; A. Greer; R. Gao; J. F. Liebman "Paradigms and Paradoxes: Energetics of the Oxidative Cleavage of Indigo," Struct. Chem., 18, 71-74. (Books and Publications: Peer Reviewed Article) 2007

A. T. Frank; N. S. Farina; N. Sawwan; O. R. Wauchope; M. Qi; E. M. Brzostowska; W. Chan; F. W. Grasso; P. Haberfield; A. Greer "Natural Macromolecules Have a Possible Limited Structural Diversity" Molecular Diversity, 11, 115-118. (Books and Publications: Peer Reviewed Article) 2007

D. Aebisher; E. M. Brzostowska; M. Adaickapillai; A. Greer "Regioselective (Biomimetic) Synthesis of a Pentasulfane From Ortho-benzoquinone," J. Org. Chem., 72, 2951-2955. (Books and Publications: Peer Reviewed Article) 2007

D. Aebisher; E. M. Brzostowska; N. Sawwan; R. Ovalle; A. Greer "Implications for the Existence of a Heptasulfur Linkage in Natural o-Benzopolysulfanes," J. Nat. Prod., 70, 1492-1494. (Books and Publications: Peer Reviewed Article) 2007

E. M. Brzostowska; M. Paulynice; R. Bentley, A. Greer "Planar Chirality Due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity," Chem. Res. Toxicol., 20, 1046-1052. (Books and Publications: Peer Reviewed Article) 2007

N. Sawwan; A. Greer "Rather Exotic Types of Cyclic Peroxides: Heteroatom Dioxiranes," Chem. Rev., 107, 3247-3285. (Books and Publications: Peer Reviewed Article) 2007

O. R. Wauchope; S. Shakya; N. Sawwan; J. F. Liebman; A. Greer "Photocleavage of Plasmid DNA by Dibenzothiophene S-oxide Under Anaerobic Conditions," J. Sulfur Chem., 28, 11-16. (Books and Publications: Peer Reviewed Article) 2007

A. Greer "Christopher Foote's Discovery of the Role of Singlet Oxygen [1O2 (1delta g)] in Photosensitized Oxidation Reactions" Acc. Chem. Res. 2006, 39, 797-804. (Books and Publications: Peer Reviewed Article) 2006

A. Greer "Preface: Organic Chemistry of Singlet Oxygen" Tetrahedron 2006, 62, 10603-10603. (Books and Publications: Peer Reviewed Article) 2006

A. Greer; Editor. Symposium-In-Print: "Organic Chemistry of Singlet Oxygen" [In: Tetrahedron 2006; 62, 10603-10776]. (Books and Publications: Edited Book) 2006

A. Greer; O. R. Wauchope; N. S. Farina; P. Haberfield; J. F. Liebman "Paradigms and Paradoxes: Mechanisms for Possible Enhanced Biological Activity of Bilaterally Symmetrical Chemicals" Struct. Chem. 2006, 17, 347-350. (Books and Publications: Peer Reviewed Article) 2006

N. Gandra, Aaron T. Frank, O. Le Gendre, N. Sawwan, D. Aebisher, J. F. Liebman, K. N. Houk, A. Greer, and R. Gao "Possible Singlet Oxygen Generation from the Photolysis of Indigo Dyes in Methanol, DMSO, Water, and Ionic Liquid, 1-Butyl-3-methylimidazolium tetrafluoroborate" Tetrahedron 2006, 62, 10771-10776. (Books and Publications: Peer Reviewed Article) 2006

N. Sawwan; A. Greer "The Generation of Mono- and Bis-dioxiranes from 2,3-Butanedione" J. Org. Chem. 2006, 71, 5796-5799. (Books and Publications: Peer Reviewed Article) 2006

E. L. Clennan; S. E. Hightower; A. Greer "Conformationally Induced Electrostatic Stabilization of Persulfoxides. A New Suggestion for Inhibition of Physical Quenching of Singlet Oxygen by Remote Functional Groups" J. Am. Chem. Soc. 2005, 127, 11819-11827. (Books and Publications: Peer Reviewed Article) 2005

N. Sawwan; E. M. Brzostowska; A. Greer "Substituent Effects on the Reactivity of Benzo-1,2-Dithiolan-3-one 1-Oxides and Its Possible Application to the Synthesis of DNA-Targeting Drugs" J. Org. Chem. 2005, 70, 6968-6971. (Books and Publications: Peer Reviewed Article) 2005

E. M. Brzostowska(a); A. Greer "Polysulfane Antitumor Agents from o-Benzyne. An Odd-Even Alternation Found in the Stability of Products, o-C6H4Sx (x = 1 to 8)" J. Org. Chem. 2004, 69, 5483-5485. (Books and Publications: Peer Reviewed Article) 2004

T. Voloshchuk; N. S. Farina; O. R. Wauchope; M. Kiprowska; P. Haberfield; A. Greer "Molecular Bilateral Symmetry of Natural Products. Prediction of Selectivity of Dimeric Molecules by Density Functional Theory and Semiempirical Calculations" J. Nat. Prod. 2004, 67, 1141-1146. (Books and Publications: Peer Reviewed Article) 2004

A. Greer "Perspective: A View of Unusual Peroxides" Science 2003, 302, 235-236. (Books and Publications: Peer Reviewed Article) 2003

D. A. Singleton; M. J. Szymanski; M. P. Meyer; A. G. Leach; K. T. Kuwata; J. S. Chen; A. Greer; C. S. Foote; K. N. Houk "Mechanism of Ene Reactions of Singlet Oxygen. A Two-Step No-Intermediate Mechanism" J. Am. Chem. Soc. 2003, 125, 1319-28. (Books and Publications: Peer Reviewed Article) 2003

E. M. Brzostowska; A. Greer "The Role of Amine in the Mechanism of Pentathiepin (Polysulfur) Antitumor Agents" J. Am. Chem. Soc. 2003, 125, 396-404. (Books and Publications: Peer Reviewed Article) 2003

K. B. Thomas; A. Greer "Gauging the Significance of Atomic Oxygen [O(3P)] in Sulfoxide Photochemistry. A Method for Hydrocarbon Oxidation" J. Org. Chem. 2003, 68, 1886-1891. (Books and Publications: Peer Reviewed Article) 2003

A. Greer "On the Origin of Cytotoxicity of the Natural Product Varacin. A Novel Example of a Pentathiepin Reaction That Provides Evidence for a Triatomic Sulfur Intermediate" J. Am. Chem. Soc. 2001, 123, 10379-10386. (Books and Publications: Peer Reviewed Article) 2001

E. Lucien; A. Greer "Electrophilic Oxidant Produced in the Photodeoxygenation of 1,2-Benzodiphenylene Sulfoxide" J. Org. Chem. 2001, 66, 4576-4579. (Books and Publications: Peer Reviewed Article) 2001

A. Greer; G. Vassilikogiannakis; K.-C. Lee; T. S. Koffas; K. Nahm; C. S. Foote "Reaction of Singlet Oxygen with trans-4-Propenylanisole. Formation of [2+2] Products with Added Acid" J. Org. Chem. 2000, 65, 6876-6878. (Books and Publications: Peer Reviewed Article) 2000

R. Reznik; A. Greer "An Adjacent Thioester Provides Apical-Directed Stabilization to 3-Isothiazolidinone 1-Oxide Heterocycles" Chem. Res. Toxicol. 2000, 13, 1193-1198. (Books and Publications: Peer Reviewed Article) 2000

S. Wu; A. Greer "Attractive Through-Space S-O Interaction in the DNA-Cleaving Antitumor Antibiotic Leinamycin" J. Org. Chem. 2000, 65, 4883-4887. (Books and Publications: Peer Reviewed Article) 2000

A. Greer; K. A. Conklin; K. Faull; K. N. Houk; C. S. Foote "Low Temperature FAB Mass and NMR Spectroscopic Identification of an Unstable Episulfoxide" J. Org. Chem. 1999, 64, 1432-1433. (Books and Publications: Peer Reviewed Article) 1999

E. L. Clennan; M.-F. Chen; A. Greer; F. Jensen "Experimental and Computational Evidence for the Formations of Iminopersulfinic Acids" J. Org. Chem. 1998, 63, 3397-3402. (Books and Publications: Peer Reviewed Article) 1998

F. Jensen; A. Greer; E. L. Clennan "Reaction of Organic Sulfides with Singlet Oxygen. A Revised Mechanism" J. Am. Chem. Soc. 1998, 120, 4439-4449. (Books and Publications: Peer Reviewed Article) 1998

A. Greer; M.-F. Chen; F. Jensen; E. L. Clennan "Experimental and ab Initio Computational Evidence for New Peroxidic Intermediates (Iminopersulfinic Acids). Substituent Effects in the Photooxidations of Sulfenic Acid Derivatives" J. Am. Chem. Soc. 1997, 119, 4380-4387. (Books and Publications: Peer Reviewed Article) 1997

A. Greer; F. Jensen; E. L. Clennan "Ring Strain Effects on the Interconversion of Intermediates in the Reaction of Organic Sulfides with Singlet Oxygen" J. Org. Chem. 1996, 61, 4107-4110. (Books and Publications: Peer Reviewed Article) 1996

E. L. Clennan; A. Greer "Steric and Electronic Effects on the Partitioning of a Persulfinyl Intermediate Along the Physical Quenching and Chemical Reaction Channels" Tetrahedron Lett. 1996, 37, 6093-6096. (Books and Publications: Peer Reviewed Article) 1996

E. L. Clennan; A. Greer "The Effect of Alcohols on the Photooxidative Behavior of Diethylsulfide" J. Org. Chem. 1996, 61, 4793-4797. (Books and Publications: Peer Reviewed Article) 1996

E. L. Clennan; P. Dobrowolski; A. Greer "Reaction of Singlet Oxygen with Thietane. A Novel Example of a Self-Catalyzed Reaction Which Provides Evidence for a Thiadioxirane Intermediate" J. Am. Chem. Soc. 1995, 117, 9800-9803. (Books and Publications: Peer Reviewed Article) 1995

Awards, Honors and Fellowships
National Institutes of Health, SCORE grant: Title "Biosynthetic Formation of Polysulfane Anticancer Agents"; March 2006-Feb. 2010; $719,262 (includes indirect costs). (Grants and Fellowships) 2006

Sara Jane Rhoads Award for Outstanding Research for the Ph.D. Degree, University of Wyoming and the American Chemical Society, 1996. (Awards and Honors) 1996

Professional Leadership
American Chemical Society's Subcommittee on Scientific Freedom and Human Rights (Professional Leadership: Public Service) 2009

Associate Editor, Photochemistry and Photobiology (Wiley-Blackwell) (Professional Leadership: Public Service) 2009

Board Member, Committee of Concerned Scientists
(http://concernedscientists.org/) (Professional Leadership: Public Service) 2009

Other Professional Activities
Board of Editors: Molecular Diversity section of the journal Molecules, elected 2008

Board of Editors: Research Letters in Organic Chemistry (Hindawi Publishers), elected 2008

Board of Editors: Structural Chemistry (Springer Publishers), elected 2006

Deputy Executive Officer, Department of Chemistry, The Graduate Center CUNY 2004