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University of Connecticut Department of Chemistry Peczuh Research Group

Publications


  • A practical and scalable synthesis of carbohydrate based oxepines
    • Vannam, R.; Peczuh, M. W.
    • Org. Biomol. Chem. 2016, 14, 3989-3996, DOI: 10.1039/C6OB00262E
    • Document Link

  • How to Homologate Your Sugar: Synthetic Approaches to Septanosyl Containing Carbohydrates
    • Vannam, R.; Peczuh, M.W.
    • Eur. J. Org. Chem. 2016, 1800-18112, DOI: 10.1002/ejoc.201600052
    • Document Link

  • Rules of Macrocycle Topology: A [13]-Macrodilactone Case Study
    • Magpusao, A. N.; Rutledge, K. M.; Hamlin, T. A.; Lawrence, J.-M.; Mercado, B. Q.; Leadbeater, N. E.; Peczuh, M. W.
    • Chem. Eur. J. 2016, 22, 6001-6011, DOI: 10.1002/chem.201504684
    • Document Link

  • Turning Spiroketals Inside Out: A Rearrangement Triggered by an Enol Ether Epoxidation
    • Lorenc, C.; Sauri, J.; Moser, A.; Buevich, A. V.; Williams, A. J.; Williamson, R. T.; Martin, G. E.; Peczuh, M. W.
    • Chemistry Open 2015, 4, 577-580, DOI: 10.1002/open.201500122
    • Document Link
    • Cover Article

  • Synthesis, structure and reactivity of [15]-macrodilactones
    • Si, D.; Peczuh, M. W.
    • Org. Biomol. Chem. 2015, 13, 6463-6467, DOI: 10.1039/C5OB00809C
    • Document Link

  • Stereogenic α-carbons determine the shape and topology of [13]-macrodilactones
    • Magpusao, A. N.; Rutledge, K.; Mercado, B.; Peczuh, M. W.
    • Org. Biomol. Chem. 2015, 13, 5086-5089, DOI: 10.1039/C5OB00402K
    • Document Link

  • Cardiac glycoside activities link Na+/K+ ATPase ion-transport to breast cancer cell migration via correlative SAR
    • Magpusao, A. N.; Omolloh, G.; Johnson, J.; Gascon, J.; Peczuh, M. W.; Fenteany, G.
    • ACS Chem. Biol. 2015, 10, 561-569, DOI: 10.1021/cb500665r
    • Document Link

  • Ultrasensitive carbohydrate-peptide SPR imaging microarray for diagnosing IgE mediated peanut allergy

  • De novo macrolide–glycolipid macrolactone hybrids: Synthesis, structure and antibiotic activity of carbohydrate-fused macrocycles
    • Desmond, R. T., Magpusao, A. N., Lorenc, C., Alverson, J. B., Priestley, N., Peczuh, M. W.
    • Beilstein J. Org. Chem. 2014, 10, 2215-2221, DOI: 10.3762/bjoc.10.229
    • Document Link

  • Synthesis, structure and reactivity of a macrocyclic imine: aza-[13]-macrodiolides
    • Ma, J.; Vannam, R.; Terwilliger, D. W.; Peczuh, M. W.
    • Tetrahedron Lett. 2014, 55, 4255-4259, DOI: 10.1016/j.tetlet.2014.05.081
    • Document Link

  • Positioning and Configuration of Key Atoms Influence the Topology of [13]-Macrodiolides
    • Ma, J.; Peczuh, M. W.
    • J. Org. Chem. 2013, 78, 7414-7422, DOI: 10.1021/jo400383g
    • Document Link

  • Synthesis of C-Septanosides from Pyranoses via Vinyl Addition and Electrophilic Cyclization
    • Vannam, R.; Peczuh, M. W.
    • Org. Lett. 2013, 15, 4122-4125, DOI: 10.1021/ol401769k
    • Document Link

  • Glycosylations with a septanosyl fluoride donor lacking a C2 protecting group.
    • Saha, J.; Peczuh, M. W.
    • Tetrahedron Lett. 2012, 53, 5667-5670, DOI:10.1016/j.tetlet.2012.08.039
    • Document Link

  • C2 Hydroxyl Group Governs the Difference in Hydrolysis Rates of Methyl-α-D-glycero-D-guloseptanoside and Methy-β-D-glycero-D-guloseptanoside.
    • Beck, J. M.; Miller, S. M.; Peczuh, M. W.; Hadad, C. M.
    • J. Org. Chem. 2012, 77, 4242-4251.
    • Document Link

  • Discovery of a Phosphine-Mediated Cycloisomerization of Alkynyl Hemiketals: Access to Spiroketals and Dihydropyrazoles via Tandem Reactions.
    • Saha, J.; Lorenc, C.; Surana, B.; Peczuh, M. W.
    • J. Org. Chem. 2012, 77, 3846-3858.
    • Document Link

  • Synthesis and Properties of Septanose Carbohydrates.
    • Saha, J.; Peczuh, M. W.
    • Adv. Carb. Chem. & Biochem. 2011, 66, 121-186. ISBN: 978-0-12-385518-3
    • Document Link

  • Septanosyl fluorides as glycosyl donors: Synthesis of 2-amino septanosyl glycoconjugates.
    • Saha, J.; Peczuh, M. W.
    • Chem. Eur. J. 2011, 17, 7357-7365.
    • Document Link

  • Tandem cyclization and acetalization of a homologate D-glucose delivers D-glycero-D-guloseptanosides.
    • Ramsubhag, R. R; Peczuh, M. W.
    • Arkivoc 2011, v, 92-101.
    • Document Link

  • Computational and experimental investigation of mono-septanoside binding by Concanavalin A: Correlation of ligand stereochemistry to enthalpies of binding.
    • Duff, M. R.; Fyvie, W. F.; Markad, S. D.; Frankel, A. E.; Kumar, C. V.; Gascón, J. A.; Peczuh, M. W.
    • Org. Biomol. Chem. 2011, DOI: 10.1039/C0OB00425A.
    • Document Link

  • Synthesis and evaluation of antimigratory and antiproliferative activities of lipid-linked [13]-macro-dilactones.
    • Magpusao, A. N.; Desmond, R. T.; Billings, K. J.; Fenteany, G.; Peczuh, M. W.
    • Bioorg. Med. Chem. Lett. 2010, 20, 5472-5476.
    • Document Link

  • Electrochemical Immunosensors for Antibodies to Peanut Allergen Ara h2 Using Gold-Peptide Nanoparticle Films. Anal.
    • Liu, H.; Malhotra, R.; Peczuh, M. W.; Rusling, J. F.
    • Chem. 2010, 82, 5865-5871. doi: 10.1021/ac101110q
    • Document Link

  • Hydroxyl group orientation affects hydrolysis rates of methyl a-septanosides.
    • Markad S.D.; Miller, S. M.; Morton, M.; Peczuh, M. W.
    • Tetrahedron Lett. 2010, 51, 1209-1212 doi: 10.1016/j.tetlet.2009.12.109.
    • Document Link

  • Access to Ring Expaned Analogs of 2-Amino Sugars.
    • Saha, J.; Peczuh, M. W.
    • Org. Lett. 2009, 11, 4482-4484.
    • Document Link

  • An unexpectedly facile cyclization of polyhydric alcohols.
    • Pavlik, C.; Onorato, A.; Castro, S.; Morton, M.; Peczuh, M. W.; Smith, M. B.
    • Org. Lett. 2009, 11, 3722-3725.
    • Document Link

  • An oxepinone route to carbohydrate based oxepines.
    • Castro, S.; Johnson, C. S.; Surana, B.; Peczuh, M. W.
    • Tetrahedron 2009, 65, 7921-7926.
    • Document Link

  • Remote induction of asymmetry in [13]-macro-dilactone topology by a single stereogenic center.
    • Fyvie, W. S.; Peczuh, M. W.
    • Chem. Commun. 2008, 4028-4030.
    • Document Link

  • Diastereoselectivity in Epoxidation of Carbohydrate Fused [13]-Macro-dilactones.
    • Fyvie, W. S.; Peczuh, M. W.
    • J. Org. Chem. 2008 73, 3626-3629.
    • Document Link

  • Stereoselectivity in the Epoxidation of Carbohydrate Based Oxepines.
    • Markad, S.; Xia, S.; Surana, B.; Morton, M. D.; Hadad, C. M.; Peczuh, M. W.
    • J. Org. Chem. 2008, 73, 6341-6354.
    • Document Link

  • Synthesis of substituted septanosyl 1,2,3-triazoles.
    • Castro, S.; Cherney, E. C.; Peczuh, M. W.
    • Carbohydrate Research, 2007, 342, 1366-1372.
    • Document Link

  • Conformational Analysis of Methyl 5-O-methyl Septanosides: Effect of Glycosylation on Conformer Populations.
    • DeMatteo, M.; Mei, S.; Fenton, R.; Morton, M.; Baldisseri, D. M.; Hadad, C. M.; Peczuh, M. W.
    • Carbohydrate Research, 2006, 341, 2927-2945.
    • Document Link

  • Recent Developments in the Synthesis of Oxepines.
    • Snyder, N. L.; Haines, H.; Peczuh, M. W.
    • Tetrahedron 2006, 62, 9301-9320.
    • Document Link

  • Synthesis of a-D-Idoseptanosyl Glycosides Using an S-Phenyl Septanoside Donor.
    • Castro, S.; Fyvie, W. S.; Hatcher, S.; Peczuh, M. W.
    • Org. Lett. 2005, 7, 4709-4712 .
    • Document Link

  • Recognition of Septanose Carbohydrates by Concanavalin A.
    • Castro. S.; Duff, M; Snyder, N.; Morton, M. Kumar, C. V.; Peczuh, M. W.
    • Org. Biomol. Chem. 2005, 3, 3869- 3872.
    • Document Link

  • Sequential Cyclization-Elimination Route to Carbohydrate Based Oxepines.
    • Castro. S.; Peczuh, M. W.;
    • J. Org. Chem. 2005, 70, 3312-3315.
    • Document Link

  • Septanose Carbohydrates: Synthesis and Conformational Studies of Methyl a-D-Glycero-D-idoseptanoside and Methyl b-D-Glycero-D-guloseptanoside.
    • DeMatteo, M.; Snyder, N. L.; Morton, M.; Baldisseri, D. M.; Hadad, C. M.; Peczuh, M. W.;
    • J. Org. Chem. 2005, 70, 24-38.
    • Document Link

  • Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose based oxepine: intramolecular cyclization in the absence of a glycosyl acceptor.
    • Fyvie, W. S.; Morton, M.; Peczuh, M. W.
    • Carbohydr. Res. 2004, 339, 2363-2370.
    • Document Link

  • Synthesis, crystal structure and reactivity of a D-xylose based oxepine.
    • Peczuh, M. W.; Snyder, N. L.; Fyvie, W. S.
    • Carbohydr. Res. 2004, 339, 1163-1171.
    • Document Link

  • Benzothianthrene oxide. Electronic Encylopedia of Reagents for Organic Synthesis (eEROS)
    • Peczuh, M. W.; Malosh, C. F.
    • (Paquette, L. A. Editor) John Wiley & Sons (2003).
    • Document Link

  • Carbohydrate Based Oxepines: Ring Expanded Glycals for the Synthesis of Septanose Saccharides.
    • Peczuh, M. W.; Snyder, N. L.
    • Tetrahedron Lett. 2003, 44, 4057-4061.
    • Document Link

  • The Structural Basis for the Induction of VanB Resistance.
    • Dong, S.D.; Oberthur, M.; Losey, H. C.; Eggert, U. S.; Anderson, J.; Peczuh, M. W.; Walsh, C.T.; Kahne, D.
    • J. Am. Chem. Soc., 2002, 124, 9064-9065.

  • Action of Glycosyltransferases in the Maturation of Vancomycin and Teicoplanin Aglycones: Novel Glycopeptides.
    • Losey, H. C.; Peczuh, M. W.; Chen, Z.; Eggert, U. S.; Dong, S. D.; Pelczer, I.; Kahne, D.; Walsh, C. T. Tandem
    • Biochemistry, 2001, 40, 4745-4755.

  • In Recognition of Proteins.
    • Peczuh, M. W.; Orner, B. P.; Hamilton, A. D.
    • Chem. Brit. 2000, 36, 43-45.

  • Side chain elongation causes a change from enthalpy driven to entropy driven binding in the molecular recognition of tetraanionic peptides.
    • Salvatella, X.; Peczuh, M. W.; Gairí M.; Jain, R. K.; Sánchez-Quesada, J.; de Mendoza, J.; Hamilton, A. D.; Giralt, E.
    • Chem. Comm. 2000, 1399-1400.

  • Peptide and Protein Recognition by Designed Molecules.
    • Peczuh, M.W.; Hamilton, A.D.
    • Chem. Rev. 2000, 100, 2479-2494.

  • Surface Recognition and Helix Stabilization of a Tetraaspartate Peptide by Shape and Electrostatic Complementarity of an Artificial Receptor.
    • Haack, T.; Peczuh, M.W.; Salvatella, X.; Hamilton, A.D.; Sanchez-Quesada, J.; de Mendoza, J.; Giralt, E.
    • J. Am. Chem. Soc., 1999,121 , 11813-11820.

  • Molecular recognition of anionic patches on protein surfaces.
    • Giralt, Ernest; Salvatella, Xavier; Gairi, Marga; Haack, Thomas; Mendoza, Javier; Peczuh, Mark W.; Hamilton, Andrew D.
    • Peptides 1998, Proceedings of the European Peptide Symposium, 25th, Budapest, Aug. 30-Sept. 4, 1998 (1999), Ed: Bajusz, Sandor; Hudecz, Ferenc.

  • Recognition and Stabilization of an a-Helical Peptide by a Synthetic Receptor.
    • Peczuh, M.W.; Hamilton, A.D.; Sanchez-Quesada, J.; de Mendoza, J.; Haack, T.; Giralt, E.
    • J. Am. Chem. Soc., 1997,119, 9327-9328.

  • Design, Synthesis and Evaluation of Synthetic Receptors for the Recognition of Aspartate Pairs in an a-Helical Conformation.
    • Albert, J.S.; Peczuh, M.W.; Hamilton, A.D.
    • Bioorg.Med.Chem., 5(8):1455-1467, 1997.

lab photo