Characterization and Fate of a Septanosyl Ferrier Cation in the Gas and Solution Phases

  • Greis, K.; Griesbach, C.; Kirschbaum, C.; Meijer, G.; von Helden, G.; Pagel, K.; Peczuh, M. W.
  • J. Org. Chem. 2023, 88, 5543-5553. DOI: 10.1021/acs.joc.3c00079
  • Document Link


A new route to preacinetobactin enables preparation of C5-analogs

  • Bray, J.; Pierce, S.; Angeles-Boza, A.; Peczuh, M. W.
  • Molecules 2022, 27, 3688-3700. DOI: 10.3390/molecules27123688
  • Document Link


Synthesis of a diacetonide-protected, mannose-based oxepine: configurational control of anomeric acetate activation

  • Pero, B.; Peczuh, M. W.
  • J. Org. Chem. 2022, 87, 7474-7479. DOI: 10.1021/acs.joc.2c00206
  • Document Link


Synthesis of ring-expanded homologs of 3-amino pyranosides

  • Bosko, C.; Vannam, A.; Peczuh, M. W.
  • Tetrahedron Lett. 2022, e153699. DOI: 10.1016/j.tetlet.2022.153699
  • Document Link


Characterization of the Low Energy Conformations and Differential Reactivities of D-Glucose and D-Mannose Based Oxepines

  • Griesbach, C.E.; Peczuh, M.W.
  • Org. Biomol. Chem. 2021, 19, 10635-10646. DOI: 10.1039/D1OB01900G
  • Document Link


Indolyl Septanoside Synthesis for In Vivo Screening of Bacterial Septanoside Hydrolases

  • Pote, A.R.; Pascual, S.; Planas, A.; Peczuh, M.W.
  • Int. J. Mol. Sci. 2021, 22, 4497. DOI: 10.3390/ijms22094497
  • Document Link


Amino [13]-macrodilactones: synthesis, derivatization, and structural motifs

  • Chen, C.; Lawrence, J.-M.; Peczuh, M.W.
  • Tetrahedron Lett. 2020, 61(48), (Article 152579). DOI: 10.1016/j.tetlet.2020.152579
  • Document Link


Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation

  • Rutledge, K. M.; Mercado, B.; Griesbach, C.; Peczuh, M. W.
  • Acta Cryst. 2020, E76, 1617-1623. DOI: 10.1107/S2056989020012037
  • Document Link


Exploring the physicochemical and antiproliferative properties of biaryl-linked [13]-macrodilactones

  • Chen, C.; Bosko, C.; McGeough, K.; McLean, R.; Hadden, K.; Peczuh, M. W.
  • Bioorg. Med. Chem. 2020, 28 (Article 115671) DOI: 10.1016/j.bmc.2020.115671
  • Document Link


A method for preparing N-alkylated kanosamines from diacetone D-glucose

  • Cannone, Z.; Peczuh, M. W.
  • Tetrahedron Lett. 2019, 60, 1830-1833. DOI: 10.1016/j.tetlet.2019.06.012
  • Document Link


Post Glycosylation Diversification (PGD): An Approach for Assembling Collections of Glycosylated Small Molecules

  • Cannone, Z.; Shaqra, A.; Lorenc, C.; Keshipeddy, S.; Robinson, V.; Zweifach, A.; Wright, D.; Peczuh, M. W.
  • ACS Comb. Sci. 2019, 21, 192-197, DOI: 10.1021/acscombsci.8b00139
  • Document Link


Formation of and Glycosylation with Per-O-Acetyl Septanosyl Halides: Rationalizing Complex Reactivity En Route to p-Nitrophenyl Septanosides

  • Pote, A.R.; Vannam, R.; Richard, A.; Gascón, J.; Peczuh, M. W.
  • Eur. J. Org. Chem. 2018, 1709-1719, DOI: 10.1002/ejoc.201800310
  • Document Link


Epitope Resolved Detection of Peanut Specific IgE Antibodies by SPR Imaging

  • Shen, M.; Joshi, A. A.; Vannam, R.; Dixit, C. K.; Hamilton, R. G.; Kumar, C. V.; Rusling, J. F.; Peczuh, M. W.
  • ChemBioChem, 2018, 19, 199-202, DOI: 10.1002/cbic.201700513
  • Document Link


The price of flexibility – a case study on septanoses as pyranose mimetics

  • Sager, C. P.; Fiege, B.; Zihlmann, P.; Vannam, R.; Rabbani, S.; Jakob, R. P.; Preston, R. C.; Zalewski, A.; Maier, T.; Peczuh, M. W.; Ernst, B.
  • Chem. Sci., 2018, 9, 646-654, DOI: 10.1039/C7SC04289B
  • Document Link


Macrocycles All Aflutter: Substi-tution at an Allylic Center Reveals Conformational Dynamics of [13]-Macrodilactones

  • Rutledge, K. M.; Hamlin, T. A.; Baldisseri, D.; Peczuh, M. W.
  • Chem. Asian J., 2017, 12, 2623-2633, DOI: 10.1002/asia.201700997
  • Document Link


Unequivocal Determination of Complex Molecular Structures Using Anisotropic NMR Measurements

  • Liu, Y.; Saurí, J.; Mevers, E.; Peczuh, M. W.; Hiemstra, H.; Clardy, J.; Martin, G. E.; Williamson, R. T.
  • Science, 2017, 356, eaam5349, DOI: 10.1126/science.aam5349
  • Document Link


Selective formation and rupture of 1,4-anhydroseptanoses

  • Vannam, R.; Pote, A.R.; Peczuh, M. W.
  • Tetrahedron 2017, 73, 418-425, DOI: 10.1016/j.tet.2016.12.031
  • Document Link


Synthesis and structure of a carbohydrate fused [15]-macrodilactone

  • Si, D.; Peczuh, M. W.
  • Carbohydr. Res. 2016, 434, 113-120, DOI: 10.1016/j.carres.2016.08.010
  • Document Link


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


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.


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.


Diastereoselectivity in Epoxidation of Carbohydrate Fused [13]-Macro-dilactones.


Stereoselectivity in the Epoxidation of Carbohydrate Based Oxepines.


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.


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.


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


Computational and Experimental Investigation of Mono-septanoside Binding by Concanavalin A: Correlation of Ligand Stereochemistry to Enthalpies of Binding.


Septanose Carbohydrates: Synthesis and Conformational Studies of Methyl α-D-Glycero-D-idoseptanoside and Methyl β-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.


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.


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.
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