Faculty and Staff

View faculty members by
• Alphabetical Listing
• Research Interests
• Departmental Divisions

Summary

My research interests are in synthetic organic chemistry, including the development of new synthetic methods and the synthesis of natural products. Over the last 29 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.

Synthesis of natural products

By applying this new chemistry, we have completed syntheses (since 1992) of slaframine, tetrahydropseudodistomin, capuramycin, trehazolin, the shimofuridin nucleoside disaccharide, the protein kinase C inhibitor penazetidine, the ezomycin nucleoside disaccharide, the sialidase inhibitor siastatin B, the adenosine phosphodiesterase inhibitor griseolic acid B, the liposidomycin diazepanone nucleoside, and octosyl acid A. Natural products under current investigation (shown at right) include griseolic acid A, the Mycobacterium tuberculosis detoxifying agent mycothiol, and the nucleoside antiobiotic liposidomycin B. In other recent work, we have designed novel glycosidase inhibitors as a means to elucidate enzyme function and mechanism, have developed new syntheses, transformations, and applications of thioglycosides, and have built and characterized porphyrin and chlorin dimers to help understand the structure and photophysics of the bacterial and plant photosystems.

Spencer Knapp. The Tethered Nitrogen in Natural Products Synthesis Chem. Soc. Rev. 1999, 28, 61.

Robert T. Stibrany, Spencer Knapp, Joseph A. Potenza, and Harvey J. Schugar. The Product of a Novel Aminalization, Bis[bis(3,5-dimethylpyrazol-1-yl)(dimethylamino)methane]copper(II) perchlorate Bis(dichloromethane) Inorg. Chem. 1999, 38, 132.

Spencer Knapp and Krishnan Malolanarasimhan. Oligomeric Thioglycosides with alpha-D-Manno-(1->2) Linkages from a Glycal-1,2-Episulfide Org. Lett . 1999, 1, 611.

Spencer Knapp, Buwen Huang, Thomas J. Emge, Suzie Sheng, Karsten Krogh-Jespersen, Joseph A. Potenza, and Harvey J. Schugar. A Pyropheophorbide Dimer with Single Pyrrole pi Overlap and a Low-Energy Q Absorption J. Am. Chem. Soc. 1999, 121, 7977.

Spencer Knapp and Vijay K. Gore. Synthesis of the Ezomycin Nucleoside Disaccharide Org. Lett. 2000, 2, 1391.

Stephen Fox, Robert T. Stibrany, Joseph A. Potenza, Spencer Knapp, and Harvey J. Schugar. Copper (II) and Nickel (II) Complexes of Binucleating Macrocyclic Bis(disulfide)tetramine Ligands Inorg. Chem. 2000, 39, 4950.

Joseph A. Potenza, Thomas J. Emge, Jennifer Albaneze, Spencer Knapp, and Harvey J. Schugar. A Spiro-linked Pyrene-naphthoquinone Acta Cryst. 2000, C56, 1494.

Spencer Knapp and Dalian Zhao. Synthesis of the Sialidase Inhibitor Siastatin B Org. Lett. 2000, 2, 4037.

Brian Mark, David J. Vocadlo, Spencer Knapp, Barbara L. Triggs-Raine, Stephen G. Withers, and Michael N. G. James. Crystallographic Evidence for Substrate-assisted Catalysis in a Bacterial -Hexosaminidase J. Biol. Chem. 2001, 276, 10330.

Spencer Knapp and David S. Myers. alpha-GlcNAc Thioconjugates J. Org. Chem. 2001, 66, 3636.

Spencer Knapp, Gregori J. Morriello, Santosh R. Nandan, Thomas J. Emge, George A Doss, and Lijian Chen. Assignment of the Liposidomycin Diazepanone Stereochemistry J. Org. Chem. 2001, 66, 5822.

Spencer Knapp, Machender R. Madduru, Zhijian Lu, Gregori J. Morriello, Thomas J. Emge, and George A. Doss. Synthesis of Griseolic Acid B by pi-Face-Dependent Radical Cyclization Org. Lett. 2001, 3, 3583-3585.

Brian L. Mark, David J. Vocadlo, Dalian Zhao, Spencer Knapp, Stephen G. Withers, and Michael N. G. James. Biochemical and Structural Assessment of the 1-N-Azasugar GalNAc-isofagomine as a Potent Family 20 -N-acetylhexosaminidase Inhibitor J. Biol. Chem. 2001, 276, 42131-42137.

Spencer Knapp, Gregori J. Morriello, and George A. Doss. Synthesis of the Liposidomycin Diazepanone Nucleoside Org. Lett. 2002, 4, 603.

Spencer Knapp and David S. Myers. Synthesis of alpha-GalNAc Thioconjugates from an alpha-GalNAc Mercaptan J. Org. Chem. 2002, 67, 2995.

Spencer Knapp, Gregori J. Morriello, and George A. Doss. A Stevens Rearrangement Thwarts Glycosylation with Liposidomycin Diazepanone Ribofuranosyl Donors Tetrahedron Lett. 2002, 43, 5797.

Spencer Knapp and Etzer Darout. The Surprise Synthesis of alpha-GlcNAc 1-C-Sulfonates Tetrahedron Lett. 2002, 43, 6075.

Spencer Knapp, Chunhua Yang, and Thomas Haimowitz. Addition of Trialkylaluminium Reagents to Glyconolactones. Synthesis of 1-C-Methyl GlcNAc Oxazoline and Thiazoline Tetrahedron Lett. 2002, 43, 7101.

Spencer Knapp, Silvia Gonzalez, David S. Myers, Lisa L. Eckman, and Carole A. Bewley. A Shortcut to Mycothiol Analogues Org. Lett. 2002, 4, 4337.

Spencer Knapp, Gregori J. Morriello, and George A. Doss. Stereoselective Ring Contraction Diverts the Mitsunobu Reaction of a 6-Hydroxy-1,4-diazepan-2-one Tetrahedron Lett. 2003, 44, 2645.

Thomas J. Emge, Matthew J. Clements, David S. Myers, and Spencer Knapp. Structure of (5-Bromopyrrol-3-yl)-cyclohexyl-methanone Acta Cryst. 2003, E59, 1.

Brian L. Mark, Don J. Mahuran, Maia M. Cherney, Dalian Zhao, Spencer Knapp, and Michael N. G. James. Crystal Structure of Human β-Hexosaminidase B: Understanding the Molecular Basis of Sandhoff and Tay-Sachs Disease J. Mol. Biol. 2003, 327, 1093.

Zhang, X.; Fried, A.; Knapp, S.; Goldman, A. S. Novel Synthesis of Enamines by Iridium-Catalyzed Dehydrogenation of Tertiary Amines Chem. Commun. 2003, 2060.

Spencer Knapp and Brian A. Kirk. Glycosylation with 2'-Thio-S-acetyl Participation Tetrahedron Lett. 2003, 44, 7601.

Spencer Knapp, Benjamin Amorelli, and George A. Doss. A Fused GalNAc-thiazole from a Singular and Unanticipated Fragmentation Tetrahedron Lett. 2004, 45, 8507.

Spencer Knapp and Etzer Darout. New Reactions of Selenocarboxylates Org Lett. 2005, 7, 203.

Spencer Knapp, Benjamin Amorelli, Etzer Darout, Christian C. Ventocilla, Lawrence M. Goldman, Richard A. Huhn, and Ellen C. Minnihan. A Family of Mycothiol Analogues J. Carbohydr. Chem. 2005, 24, 103.

Spencer Knapp, Chunhua Yang, Srihari Pabbaraja, Brian Rempel, Steven Reid, and Stephen G. Withers. Synthesis and Kinetic Analysis of the N-Acetylhexosaminidase Inhibitor XylNAc-Isofagomine J. Org. Chem. 2005, 70, 7715.

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, 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} Organic Syntheses 2007, 84, 68.

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” Organic Lett. 2007, 8, 1359.