个人简介

Education B.A. 1972, Ph.D. 1975, Cornell University (Jerrold Meinwald) NIH Postdoctoral 1975-1977, Harvard University (E. J. Corey) Awards & Honors National Cancer Institute Young Investigator Award 1978-81 American Cyanamid Faculty Award 1992 Hoechst Celanese Innovative Research Award 1995

研究领域

Organic Chemistry

Total synthesis of natural products and the development of new synthetic methods My research interests are in synthetic organic chemistry, including the development of new synthetic methods and the synthesis of natural products. Over the last 36 years we have developed methods for the stereoselective functionalization of alkenes, the construction of a variety of nitrogen and sulfur containing heterocycles, and the selective synthesis and transformation of carbohydrates and nucleosides. Methods for the oxido-accelerated retro-Diels-Alder reaction, "iodolactamization", carboxylate selenonation, and the N-benzoylcarbamate and carbonimidothioate cyclizations were developed in these labs. We have applied this chemistry to the synthesis of approximately 20 natural products, including slaframine, tetrahydropseudodistomin, capuramycin, trehazolin, conduritol A, rosmariquinone, the shimofuridin nucleoside disaccharide, the protein kinase C inhibitor penazetadine, the ezomycin nucleoside disaccharide, the sialidase inhibitor siastatin B, the adenosine phosphodiesterase inhibitor griseolic acid B, the liposidomycin diazepanone nucleoside, and the M. tuberculosis detoxifier mycothiol. In other recent work, we have built and characterized porphyrin and chlorin dimers to help understand the structure and photophysics of the bacterial and plant photosystems, have investigated new syntheses, transformations, mechanisms, and applications of thioglycosides and seleninates, and have designed novel glycosidase inhibitors as a means to elucidate enzyme function and mechanism.

近期论文

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Spencer Knapp, Richard C. Huhn, and Benjamin Amorelli. "Thionation: GlcNAc-Thiazoline Triacetate {(3aR,5R,6S,7R,7aR)-5-Acetoxymethyl-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole}" Org. Synth. 2007, 84, 68. Spencer Knapp, Etzer Darout, and Benjamin Amorelli. "New Glycomimetics: Anomeric Sulfonates, Sulfenamides, and Sulfonamides" J. Org. Chem. 2006, 71, 1380. Spencer Knapp, Vinay V. Thakur, Machender R. Madduru, Krishnan Malolanarasimhan, Gregori J. Morriello, and George A. Doss. "Short Synthesis of Octosyl Nucleosides" Org. Lett. 2006, 7, 1335. Robert T. Stibrany, Chengmin Zhang, Thomas J. Emge, Harvey J. Schugar, Joseph A. Potenza, and Spencer Knapp. "A Tris(pyrazolyl) Arene Ligand That Selects Cu(I) over Cu(II)" Inorg. Chem. 2006, 45, 9713. Spencer Knapp and Kehinde Ajayi. "The Anomeric Pudovik Rearrangement" Tetrahedron Lett. 2007, 48, 1945. Spencer Knapp and Younong Yu. "Synthesis of the Oxygenated Pactamycin Core" Org. Lett. 2007, 8, 1359. Spencer Knapp, Mohannad Abdo, Kehinde Ajayi, Richard C. Huhn, Thomas J. Emge, Eun Ju Kim, and John A. Hanover. "Tautomeric Modifications of GlcNAc-Thiazoline" Org. Lett. 2007, 9, 2321. Eun J. Kim, Benjamin Amorelli, Mohannad Abdo,Craig J. Thomas, Dona C. Love, Spencer Knapp, and John A. Hanover. "Distinctive Inhibition of OGA Isoforms by an alpha-GlcNAc Thiolsulfonate" J. Am. Chem. Soc. 2007, 129, 14854. Alexander Gosslau, Srihari Pabbaraja, Spencer Knapp, and Kuang Yu Chen. "Trans- and Cis-Stilbene Polyphenols Induced Rapid Perinuclear Mitochondrial Clustering and p53-Independent Aptosis in Cancer Cells But Not Normal Cells" Eur. J. Pharmacol. 2008, 587, 25. Benjamin Amorelli, Chunhua Yang, Brian Rempel, Stephen G. Withers, and Spencer Knapp. "N-Acetylhexosaminidase Inhibitory Properties of C-1 Homologated GlcNAc- and GalNAc-Thiazolines" Bioorg. Med. Chem. Lett. 2008, 18, 2944. Mohannad Abdo and Spencer Knapp. "Biomimetic Seleninates and Selenonates" J. Am. Chem. Soc. 2008, 130, 9234. Chad Slawson, T. Lakshmanan, Spencer Knapp, and Gerald W. Hart. "A Mitotic GlcNAcylation/Phosphorylation Signaling Complex Alters the Post-Translational State of the Cytoskeletal Protein Vimentin" Mol. Biol. Cell 2008, 19, 4130. Mohannad Abdo,Sijiu Liu, Bo Zhou, Chad D. Walls, Spencer Knapp, and Zhong-Yin Zhang. "Seleninate in Place of Phosphate: Irreversible Inhibition of Protein Tyrosine Phosphatases" J. Am. Chem. Soc. 2008, 130, 13196. Spencer Knapp, David Fash, Mohannad Abdo, Thomas J. Emge, and Paul R. Rablen. "GlcNAc-Thiazoline Conformations" Bioorg. Med. Chem. 2009, 17, 1831. James M. Macdonald, Chris A. Tarling, Edward J. Taylor, Rebecca J. Dennis, David S. Myers, Spencer Knapp, Gideon J. Davies, and Stephen G. Withers. "Chitinase Inhibition by Chitobiose and Chitotriose Thiazolines" Angewandte Chem. Internat. Ed. Engl. 2010, 49, 2599. Kehinde Ajayi, Vinay V. Thakur, Robert C. Lapo, and Spencer Knapp. "Intramolecular alpha-Glucosaminidation: Synthesis of Mycothiol" Org. Lett. 2010, 12, 2630. Mohannad Abdo, Zong Zhang, Vern L. Schramm, and Spencer Knapp. "Electrophilic Aromatic Selenylation: New OPRT Inhibitors" Org. Lett. 2010, 12, 2982. Eun Ju Kim, Dona C. Love, Etzer Darout, Mohannad Abdo, Brian Rempel, Stephen G. Withers, Paul R. Rablen, John A. Hanover, and Spencer Knapp. "OGA Inhibition by GlcNAc-selenazoline" Bioorg. Med. Chem. 2010, 18, 7058. Mohannad Abdo and Spencer Knapp. "Mechanism of a Redox Coupling of Seleninic Acid with Thiol" J. Org. Chem., 2012, 77, 3433. Walter S. Won and Spencer Knapp. "Β-D-Arabinosyl 1-C-Sulfonic Acid" J. Sulfur Chem. 2013, 34, 33. DOI:10.1080/17415993.2012.7068 Mohannad Abdo, Zhexun Sun and Spencer Knapp. "Biohybrid -Se-S- Coupling Reactions of an Amino Acid Derived Seleninate" Molecules 2013, 18, 1963;