Organic Chemistry/Analytical Chemistry/Chemical Biology

Nagy, G.; Pohl, N. L. B.* Complete Hexose Isomer Identification with Mass Spectrometry. J. Amer. Soc. Mass Spectrom. 2015, ASAP. Vela Ramirez, J. E.; Goodman, J. T.; Boggiatto, P. M.; Roychoudhury, R.; Pohl, N. L. B.; Hostetter, J. M.; Wannemuehler, M. J.; Narasimhan, B.* Safety and biocompatibility of carbohydrate-functionalized polyanhydride nanoparticles. The AAPS Journal, 2015, 17, 256-267. Mukherjee, C.; Shiao, T. C.; Pohl, N. L. B.* Facile access to (1→3)-glucosamine linkages: Synthesis of Propyl 4,6-di-O-Benzyl-2-Deoxy-2-N-Trichloroacetyl-1-Thio-β-D-Glucopyranoside. Carbohydrate Chemistry: Proven Methods, Volume 3; 2015; Roy, R.; Vidal, S., Eds.; CRC Press, ISBN-10: 1466583576. Goodman, J. T.; Vela Ramirez, J. E.; Boggiatto, P. M.; Roychoudhury, R.; Pohl, N. L. B.; Wannemuehler, M. J.; Narasimhan, B.* Nanoparticle chemistry and functionalization differentially regulates dendritic cell-nanoparticle interactions and triggers dendritic cell maturation. Part. Part. Sys. Charact., 2014, 31, 1269-1280. Mukherjee, C.; Lin, L.; Pohl, N. L. B.* Regioselective Benzylation of 2-Deoxy-2-Aminosugars Using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers. Adv. Synth. Catal. 2014, 356, 2247-2256. Vela Ramirez, J. E.; Roychoudhury, R.; Habte, H.; Cho, M. W.; Pohl, N. L. B.; Narasimhan, B.* Carbohydrate-functionalized nanovaccines preserve HIV-1 antigen stability and activate antigen presenting cells. J. Biomater. Sci. Polym. Ed. 2014, 25, 1387-1406. Adams, J.°; Goswami, M.°; Pohl N.; Mallapragada, S. K.* Synthesis and Functionalization of Virus-Mimicking Cationic Block Copolymers with Pathogen-Associated Carbohydrates as Potential Vaccine Adjuvants. RSC Advances, 2014, 4, 15655-15663. (°These two authors contributed equally to the work.) Roychoudhury, R.; Pohl, N. L. B.* Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines. Org. Lett. 2014, 16, 1156-1159. Slade, M. C.*, Raker, J.; Kobilka, B.; Pohl, N. L. B.* A Research Module for the Organic Chemistry Laboratory: Multistep Synthesis of a Fluorous Dye Molecule. J. Chem. Educ. 2014, 91, 126-130. Goswami, M.; Ellern, A.; Pohl, N. L. B.* Bismuth(V)-mediated thioglycoside activation. Angew. Chem. Int. Ed. 2013, 52, 8441-8445. Tsabedze, S. B.; Kabotso, D. E. K.; Pohl, N. L. B.* The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents. Tetrahedron Lett. 2013, 54, 6983-6985. Ko, K.-S.; Mizanur, R. M.; Jackson, J. M.; Lin, L.; Pohl, N. L. B.* A mass-differentiated library strategy for identification of sugar nucleotidyltransferase activities from cell lysates. Anal. Biochem. 2013, 441, 8-12. Phanse, Y.; Carrillo-Conde, B. R.; Ramer-Tait, A. E.; Roychoudhury, R.; Pohl, N. L. B.; Narasimhan, B.*; Wannemuehler, M. J.*; Bellaire, B. H.* Functionalization of polyanhydride microparticles with di-mannose influences uptake by and intracellular fate within dendritic cells. Acta Biomaterialia, 2013, 9, 8902-8909. Roychoudhury, R.; Pohl, N. L. B.* Light fluorous-tag assisted synthesis of oligosaccharides. In Modern Synthetic Methods in Carbohydrate Chemistry—From Monosaccharides to Complex Glycoconjugates; Werz, D. B.; Vidal, S. Eds. Wiley-VCH, 2013, pp. 221-240, ISBN-10: 3527332847. Lin, L.; Pohl, N. L. B.* Synthesis of a series of maltotriose phosphates with an evaluation of the utility of a fluorous phosphate protecting group. Carbohydr. Res. 2013, 369, 14-24. Warner, C.; Camci-Unal, G.; Pohl, N. L. B.; Reilly, P.* Substrate Binding by the Catalytic Domain and Carbohydrate Binding Module of Ruminococcus flavefaciens FD-1 Xyloglucanase/Endoglucanase. Ind. Eng. Chem. Res. 2013, 52, 30-36. (special issue) Camci-Unal, G.; Mizanur, R. M.; Pohl, N. L. B.* Synthesis of a 3-deoxy-D-manno-octulosonic acid (KDO) building block from D-glucose via fermentation. Org. Biomol. Chem. 2012, 10, 5856-5860. (special issue) Carillo-Conde, B. R.; Roychoudhury, R.; Chaves-Santoscoy, A. V.; Narasimhan, B.; Pohl, N. L. High-throughput synthesis of carbohydrates and functionalization of polyanhydride nanoparticles. J. Vis. Exp. 2012, 65, e3967. Pohl, N. L. B.*; Streff, J.; Brokman, S. Evaluating Sustainability: Soap versus Biodiesel Production from Plant Oils. J. Chem. Educ. 2012, 89, 1053-1056. Chavez-Santoscoy, A.; Roychoudhury, R.; Pohl, N. L. B.; Wannemuehler, M. J.; Narasimhan, B.*; Ramer-Tait, A. E. Tailoring the Immune Response by Targeting C-type Lectin Receptors on Alveolar Macrophages Using "Pathogen-like" Amphiphilic Polyanhydride Nanoparticles." Biomaterials, 2012, 33, 4762-4772. Lin, L.; Abdel Motaal, B.; Schmidt-Supprian, M.; Pohl, N. L. B.* Multigram Synthesis of Isobutyl-beta-C-galactoside as a Substitute of Isopropylthiogalactoside for Exogenous Gene Induction in Mammalian Cells. J. Org. Chem. 2012, 77, 1539-1546. Edwards, H. E.; Nagappayya, S. K.; Pohl, N. L. B.* Probing the Limitations of Fluorous Content for Tag-Mediated Microarray Formation. Chem. Commun. 2012, 48, 510-512. Nagappayya, S. K.; Pohl, N. L. B.* Production of Fluorous-Based Microarrays with Uncharged Carbohydrates. In Carbohydrate Microarrays: Methods and Protocols. Methods in Molecular Biology, vol. 808, Chevolot, Y., Ed. Springer, 2011, 149-153. (invited book chapter) Carrillo-Conde, B.; Song, E.-H.; Chavez-Santoscoy, A.; Phanse, Y.; Ramer-Tait, A. E.; Pohl, N. L. B.; Wannemuehler, M. J.; Bellaire, B. H.; Narasimhan, B.* Mannose-Functionalized "Pathogen-Like" Polyanhydride Nanoparticles Target C-Type Lectin Receptors on Dendritic Cells. Mol. Pharmaceutics, 2011, 8, 1877-1886. Osanya, A.; Song, E.-H.; Metz, K.; Shimak, R. M.; Boggiatto, P. M.; Huffman, E.; Johnson, C.; Hostetter, J. M.; Pohl, N. L. B.; Petersen, C. A.* Pathogen-derived oligosaccharides improve innate immune response to intracellular parasite infection. Am. J. Pathol. 2011, 179, 1329-1337. Pohl, N. L. B.*; Kirshenbaum, K.; Yoo, B.; Schulz, N.; Zea, C. J.; Streff, J. M.; Schwarz, K. L. Student-driven design of peptide mimetics: microwave-assisted synthesis of peptoid oligomers. J. Chem. Educ. 2011, 88, 999-1001. Lin, L.; Pohl, N. L. B.* A Fluorous Phosphate Protecting Group with Applications in Carbohydrate Synthesis. Org. Lett. 2011, 13, 1824-1827. Song, E.-H.; Osanya, A. O.; Petersen, C. A.; Pohl, N. L. B.* Synthesis of multivalent tuberculosis and Leishmania-associated capping carbohydrates reveals structure-dependent responses allowing immune evasion. J. Am. Chem. Soc. 2010, 132, 11428-11430. Choi, D. W.; Bandow, N. L.; McEllistrem, M. T.; Semrau, J. D.; Antholine, W. W.; Hartsel, S. C.; Gallagher, W.; Zea, C. J.; Pohl, N. L.; Zahn, J. A.; DiSpirito, A. A.* Spectral and thermodynamic properties of methanobactin from gamme-proteobacterial methane oxidizing bacteria: A case for copper competition on a molecular level. J. Inorg. Biochem. 2010, 104, 1240-1247. Camci-Unal, G.; Pohl, N. L. B.* Thermodynamics of Binding Interactions between Divalent Copper and Chitin Fragments by Isothermal Titration Calorimetry (ITC). Carbohydr. Polym. 2010, 81, 8-13. Roychoudhury, R.; Pohl, N. L. B.* New Structures, Chemical Functions, and Inhibitors for Glycosyltransferases. Curr. Opin. Chem. Biol. 2010, 14, 168-173. (invited review) Pohl, N.* The Sugar Code: Fundamentals of Glycosciences. ChemBioChem, 2010, 11, 1147. (invited book review) Camci-Unal, G.; Pohl, N. L. B.* Quantitative Determination of Heavy Metal Contaminant Complexation by the Carbohydrate Polymer Chitin. J. Chem. Eng. Data, 2010, 55, 1117-1121. Utku, Y.; Rohatgi, A.; Yoo, B.; Zuckermann, R. N.; Pohl, N. L.; Kirshenbaum, K.* Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate lab. J. Chem. Educ. 2010, 87, 637-639. Song, E.-H.; Pohl, N. L. B.* Carbohydrate arrays: recent developments in fabrication and detection methods with applications. Curr. Opin. Chem. Biol.2009, 13, 626-632. (invited review) Collet, B. Y. M.; Nagashima, T.; Yu, M. S.; Pohl, N. L. B.* Fluorous-based Peptide Microarrays for Protease Screening. J. Fluorine Chem. 2009, 130, 1042-1048. Song, E.-H.; Pohl, N. L. B.* Fluorous-based small-molecule microarrays for protein, antibody, and enzyme screening. Future Med. Chem. 2009, 1, 889-896. (invited special report) Pohl, N. L. B. The expanding world of glycobiology. Nature Chem. Biol. 2009, 5, 373. (invited book review) Mizanur, R. M.; Pohl, N. L.* Phosphomannose isomerase/GDP-mannose pyrophosphorylase from Pyrococcus furiosus: a thermostable biocatalyst for the synthesis of guanidinediphosphate-activated and mannose-containing sugar nucleotides, Org. Biomol. Chem. 2009, 7, 2135-2139. Ko, K.-S.; Park, G.; Yu, Y.; Pohl, N. L.* Protecting Group-based Colorimetric Monitoring of Fluorous-phase and Solid-phase Synthesis of Oligoglucosamines. Org. Lett. 2008, 10, 5381-5384. Mizanur, R. M.*; Pohl, N. L.* Bacterial CMP-Sialic Acid Synthetases: Production, Properties and Applications. Appl. Microbiol. Biotechnol. 2008, 80, 757-765. (invited review) Zea, C. J.; Camci-Unal, G.; Pohl, N. L.* Thermodynamics of Binding of Divalent Magnesium and Manganese to Uridine Phosphates: Implications for Diabetes-Related Hypomagnesaemia and Carbohydrate Biocatalysis. Chem. Cent. J., 2008, 2, 15. Pohl, N. L.* Automated Solution-Phase Oligosaccharide Synthesis and Carbohydrate Microarrays: Development of Fluorous-Based Tools for Glycomics. In Chemical Glycobiology; Chen, X.; Halcomb, R.; Wang, G. P., Eds. ACS Symposium Series 990; American Chemical Society: Washington, DC, 2008, pp. 272-287. (invited book chapter) Jaipuri, F. A.; Pohl, N. L.* Toward Solution-Phase Automated Iterative Synthesis: Fluorous-tag Assisted Solution-Phase Synthesis of Linear and Branched Mannose Oligomers, Org. Biomol. Chem. 2008, 6, 2686-2691. Park, G.; Ko, K.-S.; Zakharova, A.; Pohl, N. L.* Mono- Vs. Di-fluorous Tagged Glucosamines for Iterative Oligosaccharide Synthesis. J. Fluorine Chem. 2008, online. (special issue) Pohl, N.*; Schwarz, K. Polymer-Supported Reagents and 1H-19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone. J. Chem. Educ. 2008, 85, 834-835. Pohl, N. L.* Fluorous Tags Catching on Microarrays. Angew. Chem. Int. Ed. 2008, 47, 3868-3870. (invited review) Hui, Z.; Brokman, S.; Fang, N.; Pohl, N.; Yeung, E.* Linkage Position and Residue Identification of Disaccharides by Tandem MS and Linear Discriminant Analysis, Rapid Commun. Mass Spectrom. 2008, 22, 1579-1586. Jaipuri, F. A.; Collet, B. Y. M.; Pohl, N. L.* Synthesis and Quantitative Evaluation of Glycero-D-manno-heptose Binding to Concanavalin A by Fluorous-tag Assistance. Angew. Chem. Int. Ed. 2008, 47, 1707-1710. Chen, G.-S.; Pohl, N. L.* Synthesis of Fluorous Tags for Incorporation of Reducing Sugars into a Quantitative Microarray Platform. Org. Lett. 2008, 10, 785-788. Mizanur, R. M.; Pohl, N. L.* A thermostable promiscuous glucose-1-phosphate uridyltransferase from Helicobacter pylori for the synthesis of nucleotide sugars. J. Mol. Catal. B: Enzymatic, 2008, 50, 13-19. Yu, Y.; Mizanur, R. M.; Pohl, N. L.* Glycosidase activity profiling for bacterial identification by a chemical proteomics approach. Biocatal. Biotransform. 2008, 26, 25-31. Mizanur, R. M.; Griffin, A. K. K.; Pohl, N. L.* Recombinant production and biochemical characterization of a hyperthermostable alpha-glucan/maltodextrin phosphorylase from Pyrococcus furiosus. Archaea, 2007, 2, 169-176. Mizanur, R. M.; Pohl, N. L.* Cloning and characterization of a heat-stable CMP-N-acylneuraminic acid synthetase from Clostridium thermocellum. Appl. Microbiol. Biotechnol. 2007, 76, 827-834. Pohl, N. L.* Carbohydrate Microarrays and Fluorous-Phase Synthesis: Interfacing Fluorous-Phase Tags with the Direct Formation of Glycoarrays. In Current Fluoroorganic Chemistry: New Synthetic Directions, Technologies, Materials, and Biological Applications; Soloshonok, V. A.; Mikami, K.; Yamazaki, T.; Welch, J. T.; Honek, J. F., Eds. ACS Symposium Series 949; American Chemical Society: Washington, DC, 2007, pp. 261-270. (invited book chapter) Mamidyala, S. K.; Ko, K.-S.; Jaipuri, F. A.; Park, G.; Pohl, N. L.* Noncovalent Fluorous Interactions for the Synthesis of Carbohydrate Microarrays. J. Fluorine Chem. 2006, 127, 571-579. (special issue) Choi, D. W.; Do, Y. S.; Zea, C. J.; McEllistrem, M. T.; Lee, S.-W.; Semrau, J. D.; Pohl, N. L.; Kisting, C. J.; Scardino, L. L.; Hartsel, S. C.; Boyd, E. S.; Gessey, G. G.; Riedel, T. P.; Shafe, P. H.; Kranski, K. A.; Tritsch, J. R.; Antholine, W. W.; DiSpirito, A. A.* Spectral and Thermodynamic Properties of Ag(I), Au(III), Cd(II), Co(II), Fe(III), Hg(II), Mn(II), Ni(II), Pb(II), U(IV), and Zn(II) Binding by Methanobactin from Methylosinus trichosporium OB3b. J. Inorg. Biochem. 2006, 100, 2150-2161. (special issue) Wacker, M.; Feldman, M. F.; Callewaert, N.; Kowarik, M.; Clarke, B. R.; Pohl, N. L.; Hernandez, M.; Vines, E. D.; Valvano, M. A.; Whitfield, C.; Aebi, M.* Substrate Specificity of Bacterial Oligosaccharyltransferase Suggests a Common Transfer Mechanism for the Bacterial and Eukaryotic Systems . Proc. Natl Acad. Sci., USA, 2006, 103, 7088-7093. Pohl, N. L.* Building a Bridge to New Antibiotics. ACS Chem. Biol. 2006, 1, 14-16. (invited commentary) Pohl, N. L.* Array methodology singles out pathogenic bacteria. Nature Chem. Biol. 2006, 2, 125-126. (invited commentary) Choi, D. W.; Zea, C. J; Do, Y. S.; Semrau, J. D.; Antholine, W. E.; Hargrove, M. S.; Pohl, N. L.; Boyd, E. S.; Geesey, G. G.; Hartsel, S. C.; Shafe, P. H.; McEllistrem, M. T.; Kisting, C. J.; Campbell, D.; Rao, V.; de la Mora, A. M.; DiSpirito, A. A.* Spectral, Kinetic, and Thermodynamic Properties of Cu(I)- and Cu(II)-binding by Methanobactin from Methylosinus trichosporium OB3b. Biochemistry, 2006, 45, 1442-1453. Pohl, N.* Acyclic Peptide Inhibitors of Amylases. Chem. Biol. 2005, 12, 1257-1258. (invited commentary) Ko, K.-S.; Jaipuri, F. A.; Pohl, N. L.* Fluorous-Based Carbohydrate Microarrays. J. Am. Chem. Soc.2005, 127, 13162-13163. Zea, C. J.; Pohl, N. L.* Unusual Sugar Nucleotide Recognition Elements of Mesophilic Versus Thermophilic Glycogen Synthases. Biopolymers, 2005, 79, 106-113. Dutca, L.-M.; Ko, K.-S.; Pohl, N. L.; Kostic, N. M.* Platinum(II) Complex as an Artificial Peptidase: Selective Cleavage of Peptides and a Protein by cis-[Pt(en)(H2O)2]2+ Ion under Different Irradiations. Inorg. Chem.2005, 44, 5141-5146. Ko, K.-S.; Zea, C. J.; Pohl, N. L.* Strategies for the Chemoenzymatic Synthesis of Deoxysugar Nucleotides: Substrate Binding Versus Catalysis. J. Org. Chem.2005, 70, 1919-1921. Pohl, N. L.* Functional Proteomics for the Discovery of Carbohydrate-Related Enzyme Activities. Curr. Opin. Chem. Biol.2005, 9, 76-81. (invited review) Mizanur, R. M.; Jaipuri, F. A.; Pohl, N. L.* One-Step Synthesis of Labeled Sugar Nucleotides for Protein O-GlcNAc Modification Studies by Chemical Function Analysis of an Archaeal Protein. J. Am. Chem. Soc.2005, 127, 836-837. Mizanur, R. M.; Zea, C. J.; Pohl, N. L.* Unusually Broad Substrate Tolerance of a Heat-Stable Archaeal Sugar Nucleotidyltransferase for the Synthesis of Sugar Nucleotides. J. Am. Chem. Soc.2004, 126, 15993-15998. Ko, K.-S.; Zea, C. J.; Pohl, N. L.* Surprising Bacterial Nucleotidyltransferase Selectivity in the Conversion of Carbaglucose-1-phosphate. J. Am. Chem. Soc. 2004, 126, 13188-13189. Pohl, N.* Cellular Addresses: Step One in Creating a Glycocode. Chem. Biol. 2004, 11, 891-892. (invited commentary) Yu, Y.; Ko, K.-S.; Zea, C. J.; Pohl, N. L.* Discovery of the Chemical Function of Glycosidases: Design, Synthesis, and Evaluation of Mass-differentiated Carbohydrate Libraries. Org. Lett. 2004, 6, 2031-2033. Zea, C. J.; Pohl, N. L.* General Assay for Sugar Nucleotidyltransferases Using Electrospray Ionization Mass Spectrometry. Anal. Biochem. 2004, 328, 196-202. Jaipuri, F. A.; Jofre, M. F.; Schwarz, K.; Pohl, N. L.* Microwave-assisted cleavage of Weinreb amide for carboxylate protection in the synthesis of a (R)-3-hydroxyalkanoic acid. Tetrahedron Lett. 2004, 45, 4149-4152. Zea, C. J.; Pohl, N. L.* Kinetic and Substrate Binding Analysis of Phosphorylase b Via Electrospray Ionization Mass Spectrometry: A Model for Chemical Proteomics of Sugar Phosphorylases. Anal. Biochem. 2004, 327, 107-113. Zea, C. J.; MacDonell, S. W.; Pohl, N. L.* Discovery of the Archaeal Chemical Link Between Glycogen (Starch) Synthase Families Using a New Mass Spectrometry Assay. J. Am. Chem. Soc. 2003, 125, 13666-13667. Jaipuri, F. A.; Bower, B. D.; Pohl, N. L.* Protic Acid-Catalyzed Polymerization of Beta-Lactones for the Synthesis of Chiral Polyesters. Tetrahedron: Asymmetry 2003, 14, 3249-3252. Ko, K.-S.; Kruse, J.; Pohl, N. L.* Synthesis of Isobutyl-C-galactoside (IBCG) as an Isopropylthiogalactoside (IPTG) Substitute for Increased Induction of Protein Expression. Org. Lett. 2003, 5, 1781-1783. Pohl, N. L.* Nonnatural Substrates for Polyketide Synthases and their Associated Modifying Enzymes. Curr. Opin. Chem. Biol. 2002, 6, 773-778. (invited review) Pohl, N.*; Clague. A.; Schwarz, K. Chiral Compounds and Green Chemistry in Undergraduate Organic Laboratories: Reduction of a Ketone By Sodium Borohydride And Baker’s Yeast. J. Chem. Educ.2002, 79, 727-728. Pohl, N. L.* Developing New Antibiotics With Combinatorial Biosynthesis. J. Chem. Educ. 2000, 77, 1421-1423. (invited review)