Published Articles

The following is a list of literature references to investigations conducted by the Serianni laboratory dealing with the synthesis and applications of isotopically labeled monosaccharides, oligosaccharides, nucleosides and oligonucleotides.

• 1. H. A. Nunez, T. E. Walker, R. Fuentes, J. O'Connor, A. Serianni and R. Barker, Carbon-13 As a Tool For the Study of Carbohydrate Structures, Conformations and Interactions. J. Supramol. Structure 1977, 6, 535.
  
  
• 2. A. S. Serianni, H. A. Nunez and R. Barker, Carbon-13 Enriched Carbohydrates: Preparation of Aldononitriles and Their Reduction with a Palladium Catalyst. Carbohydr. Res. 1979, 72, 71.
  
  
• 3. A. S. Serianni, E. L. Clark and R. Barker, Carbon-13 Enriched Carbohydrates: Preparation of Erythrose, Threose, Glyceraldehyde and Glycolaldehyde with [¹³C]-Enrichment in Various Carbon Atoms. Carbohydr. Res. 1979, 72, 79.
  
  
• 4. A. S. Serianni, J. Pierce and R. Barker, Carbon-13 Enriched Carbohydrates: Preparation of Triose, Tetrose and Pentose Phosphates. Biochemistry 1979, 18, 1192.
  
  
• 5. A. S. Serianni and R. Barker, Isotopically-Enriched Carbohydrates: The Preparation of [²H]-Enriched Aldoses by Catalytic Hydrogenolysis of Cyanohydrins with ²H₂. Can. J. Chem. 1979, 57, 3160.
  
  
• 6. A. S. Serianni, H. A. Nunez and R. Barker, The Cyanohydrin Synthesis: Studies with [¹³C]Cyanide. J. Org. Chem. 1980, 45, 3329.
  
  
• 7. M. L. Hayes, A. S. Serianni and R. Barker, Methyl Lactoside: 600 MHz ¹H and 75 MHz ¹³C NMR Studies of ²H and ¹³C-Enriched Compounds. Carbohydr. Res. 1982, 100, 87.
  
  
• 8. A. S. Serianni and R. Barker, ¹³C Spin-Lattice Relaxation Times of [1-¹³C]-Enriched Carbohydrates. J. Magn. Reson. 1982, 49, 335.
  
  
• 9. A. S. Serianni, J. Pierce, S. Huang and R. Barker, Anomerization of Furanose Sugars: Kinetics of Ring-Opening Reactions by ¹H and ¹³C Saturation-Transfer NMR Spectroscopy. J. Am. Chem. Soc. 1982, 104, 4037.
  
  
• 10. M. L. Hayes, N. J. Pennings, A. S. Serianni, and R. Barker, Epimerization of Aldoses by Molybdate Involving a Novel Rearrangement of the Carbon Skeleton. J. Am. Chem. Soc. 1982, 104, 6764.
  
  
• 11. R. Barker, H. A. Nunez, P. Rosevear and A. S. Serianni, ¹³C NMR Analysis of Complex Carbohydrates. Methods in Enzymology 1982, 83, V. Ginsburg. Ed., 58.
  
  
• 12. A. S. Serianni, H. A. Nunez, M. L. Hayes and R. Barker, Chemical Synthesis of Monosaccharides Enriched with Carbon Isotopes. Methods in Enzymology 1982, 89, Part D, W. Wood, Ed., 64.
  
  
• 13. A. S. Serianni, J. Pierce and R. Barker, Chemical Synthesis of Aldose Phosphates Enriched with Carbon Isotopes. Methods in Enzymology 1982, 89, Part D, W. Wood, Ed., 73.
  
  
• 14. A. S. Serianni, E. L. Clark and R. Barker, Chemical Synthesis of Aldoses Enriched with Isotopes of Hydrogen and Oxygen. Methods in Enzymology 1982, 89, Part D, W. Wood, Ed., 79.
  
  
• 15. A. S. Serianni, E. Cadman, J. Pierce, M. L. Hayes and R. Barker, Enzymatic Synthesis of Isotopically-Enriched Aldoses, Ketoses and their Phosphate Esters. Methods in Enzymology 1982, 89, Part D, W. Wood, Ed., 83.
  
  
• 16. R. Barker, E. L. Clark, H. A. Nunez, J. Pierce, P. R. Rosevear and A. S. Serianni, The Synthesis of Mono- and Oligosaccharides Enriched with Isotopes of Carbon, Hydrogen and Oxygen. In: Stable Isotopes; Schmidt, Forstel and Heinzinger, Eds., Elsevier, 1982, 719.
  
  
• 17. G. Wu, A. S. Serianni and R. Barker, Stereospecific Exchange of Methylene Protons in Tetrofuranosides: Hydroxymethyl Group Conformations in Pentofuranosides. J. Org. Chem. 1983, 48, 1750.
  
  
• 18. A. S. Serianni and R. Barker, [¹³C]-Enriched Tetroses and Tetrofuranosides: An Evaluation of the Relationship Between NMR Parameters and Furanosyl Ring Conformation. J. Org. Chem. 1984, 49, 3292.
  
  
• 19. J. Pierce, A. S. Serianni and R. Barker, Anomerization of Furanose Sugars and Sugar Phosphates. J. Am. Chem. Soc. 1985, 107, 2448.
  
  
• 20. R. Barker and A. S. Serianni, Carbohydrates In Solution: Studies With Stable Isotopes. Acc. Chem. Res. 1986, 19, 307.
  
  
• 21. M. J. King-Morris and A. S. Serianni, Hydroxide-Catalyzed Isomerization of D-[1-¹³C]Mannose: Evidence For the Involvement of 3,4-Enediols. Carbohydr. Res. 1986, 154, 29.
  
  
• 22. J. R. Snyder and A. S. Serianni, D-Idose: A One- and Two- Dimensional NMR Investigation of Solution Composition and Conformation. J. Org. Chem. 1986, 51, 2694.
  
  
• 23. A. S. Serianni and R. Barker, Synthetic Approaches to Carbohydrates Enriched with Stable Isotopes of Carbon, Hydrogen and Oxygen. In: Isotopes in the Physical and Biomedical Sciences; E. Buncel/J. R. Jones, ed., Elsevier, 1987, 211.
  
  
• 24. J. R. Snyder and A. S. Serianni, Synthesis and NMR Analysis of Unenriched and [1-¹³C]-Enriched 5-Deoxypentoses and 5-O- Methylpentoses. Carbohydr. Res. 1987, 163, 169.
  
  
• 25. J. R. Snyder and A. S. Serianni, Stable Isotopically-Enriched DL- Apiose: Synthesis, NMR Analysis and Furanose Anomerization. Carbohydr. Res. 1987, 166, 85.
  
  
• 26. T. Angelotti, M. Krisko, T. O'Connor and A. S. Serianni, [1- ¹³C]Aldono-1,4-Lactones: Conformational Studies Based on ¹H-¹H, ¹³C-¹H and ¹³C-¹³C Spin Couplings and Ab Initio Molecular Orbital Calculations. J. Am. Chem. Soc. 1987, 109, 4464.
  
  
• 27. M. J. King-Morris and A. S. Serianni, ¹³C NMR Studies of [1-¹³C]Aldoses: Empirical Rules Correlating Pyranose Ring Configuration and Conformation With ¹³C Chemical Shifts and ¹³C-¹³C Spin Couplings. J. Am. Chem. Soc. 1987, 109, 3501.
  
  
• 28. A. S. Serianni and D. M. Chipman, Furanose Ring Conformation: Application of Ab Initio Molecular Orbital Calculations To the Structure and Dynamics of the Erythrofuranose and Threofuranose Rings. J. Am. Chem. Soc. 1987, 109, 5297.
  
  
• 29. P. C. Kline and A. S. Serianni, Chiral Hydroxymethyl Groups: ¹H NMR Assignments of the Prochiral C5' Protons of Ribonucleosides. Magn. Reson. Chem. 1988, 26, 120.
  
  
• 30. M. J. King-Morris, P. Bondo, R. Mrowca and A. S. Serianni, Stable Isotopically-Substituted Carbohydrates: An Improved Synthesis of [6-¹³C]Aldohexoses. Carbohydr. Res. 1988, 175, 49.
  
  
• 31. O. Kukal, A. S. Serianni and J. Duman, Glycerol Metabolism in a Freeze-tolerant Arctic Insect: An in vivo ¹³C NMR Study. J. Comp. Physiol. B 1988, 158, 175.
  
  
• 32. J. R. Snyder and A. S. Serianni, Furanose Ring Anomerization: A Kinetic Study of the 5-Deoxy-Pentoses and 5-O-Methyl-Pentoses. Carbohydr. Res. 1988, 184, 13.
  
  
• 33. J. R. Snyder, E. R. Johnston and A. S. Serianni, Talose Anomerization: NMR Methods to Evaluate the Reaction Kinetics. J. Am. Chem. Soc. 1989, 111, 2681.
  
  
• 34. O. Kukal, J. G. Duman and A. S. Serianni, Cold-Induced Mitochondrial Degradation and Cryoprotectant Synthesis in Freeze- Tolerant Arctic Caterpillars. J. Comp. Physiol. B 1989, 158, 661.
  
  
• 35. P. C. Kline and A. S. Serianni, Chiral Hydroxymethyl Groups: ¹H NMR Assignments of the Prochiral C5' Protons of 2'- Deoxyribonucleosides. Magn. Reson. Chem. 1990, 28, 324.
  
  
• 36. A. S. Serianni, P. C. Kline and J. R. Snyder, On the Use of Model Compounds to Assess Furanose Conformation at Apyrimidinic Sites in DNA. J. Am. Chem. Soc. 1990, 112, 5886.
  
  
• 37. P. C. Kline and A. S. Serianni, [¹³C]-Enriched Ribonucleosides: Synthesis and Application of ¹³C-¹H and ¹³C-¹³C Spin-Coupling Constants to Assess Furanose and N-Glycoside Bond Conformations. J. Am. Chem. Soc. 1990, 112, 7373.
  
  
• 38. A. S. Serianni, T. Vuorinen and P. Bondo, Stable Isotopically- Enriched D-Glucose: Strategies to Introduce Carbon, Hydrogen and Oxygen Isotopes at Various Sites. J. Carbohydr. Chem. 1990, 9, 513.
  
  
• 39. E. C. Garrett and A. S. Serianni, Ab initio Molecular Orbital Calculations on Carbohydrates: Conformational Properties of Deoxygenated Furanose Sugars. In: "Computer Modeling of Carbohydrate Molecules", J. Brady and A. French, eds., ACS Symposium Series 430, 1990, p. 91.
  
  
• 40. J. Wu, T. Vuorinen and A. S. Serianni, Furanose Ring Anomerization: Kinetic and Thermodynamic Studies of the D-2-Pentuloses by ¹³C NMR Spectroscopy. Carbohydr. Res. 1990, 206, 1.
  
  
• 41. E. C. Garrett and A. S. Serianni, Ab initio Molecular Orbital Calculations on Furanose Sugars: A Study with the 6-31G* Basis Set. Carbohydr. Res. 1990, 206, 183.
  
  
• 42. T. Vuorinen and A. S. Serianni, [¹³C]-Substituted Pentos-2-uloses: Synthesis and Analysis by ¹H and ¹³C NMR Spectroscopy. Carbohydr. Res. 1990, 207, 185.
  
  
• 43. E. C. Garrett and A. S. Serianni, [1-¹³C]Alditols: Elimination of Magnetic Equivalence in ¹H and ¹³C NMR Spectra of Symmetric Compounds Through [¹³C]-Substitution. Carbohydr. Res. 1990, 208, 23.
  
  
• 44. U. L. Stafford, A. S. Serianni and A. Varma, Microcomputer Automated Synthesis of Stable Isotopically Labeled Monosaccharides. American Institute of Chemical Engineering Journal 1990, 36, 1822.
  
  
• 45. P. C. Kline, S.-G. Huang, M. L. Hayes, R. Barker and A. S. Serianni, Internuclear ¹H-¹H Distance Measurements in Carbohydrates: Proton Transient Nuclear Overhauser Enhancement and Spin-Lattice Relaxation in [¹³C]- and [²H]-Substituted Compounds. Can. J. Chem. 1990, 68, 2171.
  
  
• 46. T. Vuorinen and A. S. Serianni, Synthesis of D-erythro-2- Pentulose and D-threo-2-Pentulose: Analysis of ¹³C and ¹H NMR Spectra of [1-¹³C]- and [2-¹³C]-Substituted Compounds. Carbohydr. Res. 1990, 209, 13.
  
  
• 47. J. R. Snyder and A. S. Serianni, Deoxygenated and Alkylated Furanoses: Thorpe-Ingold Effects on Tautomeric Equilibria and Rates of Anomerization. Carbohydr. Res. 1991, 210, 21.
  
  
• 48. J. Wu and A. S. Serianni, D-Penturonic Acids: Synthesis with Stable Isotopic Substitution and Solution Studies by ¹H and ¹³C NMR Spectroscopy. Carbohydr. Res. 1991, 210, 51.
  
  
• 49. J. Wu and A. S. Serianni, Ring-Opening Kinetics of the D- Pentofuranuronic Acids. Carbohydr. Res. 1991, 211, 207.
  
  
• 50. J. Wu and A. S. Serianni, Isotope-Edited 1D and 2D NMR Spectroscopy of [¹³C]-Substituted Carbohydrates. Carbohydr. Res. 1992, 226, 209.
  
  
• 51. P. C. Kline and A. S. Serianni, [¹³C]-Substituted Erythronucleosides: Synthesis and Conformational Analysis by ¹H and ¹³C NMR Spectroscopy. J. Org. Chem. 1992, 57, 1772.
  
  
• 52. J. Wu, P. B. Bondo, T. Vuorinen and A. S. Serianni, ¹³C-¹³C Spin Coupling Constants in Aldoses Enriched with ¹³C at the Terminal Hydroxymethyl Carbon: Effect of Coupling Pathway Structure on J_CC in Carbohydrates. J. Am. Chem. Soc. 1992, 114, 3499.
  
  
• 53. A. S. Serianni, Nuclear Magnetic Resonance Approaches To Oligosaccharide Structure Elucidation. In: Glycoconjugates: Composition, Structure and Function, H. J. Allen and E. C. Kisailus, eds., Marcel-Dekker, 1992, p. 71.
  
  
• 54. J. Wu, P. B. Bondo and A. S. Serianni, Multiply ¹³C-Substituted Monosaccharides: Synthesis of D-[1,5,6¹³C₃]Glucose and D-[2,5,6-¹³C₃]Glucose. Carbohydr. Res. 1992, 226, 261.
  
  
• 55. T. Bandyopadhyay, J. Wu and A. S. Serianni, [1'-¹³C]2'- Deoxyribonucleosides: Structural and Conformational Insights Derived from ¹³C-¹H Spin Coupling Constants Involving C1'. J. Org. Chem. 1993, 58, 5513.
  
  
• 56. J. Duker and A. S. Serianni, [¹³C]-Substituted Sucrose: ¹³C-¹H and ¹³C-¹³C Spin Coupling Constants To Assess Furanose and Glycosidic Bond Conformation in Aqueous Solution. Carbohydr. Res. 1993, 249, 281.
  
  
• 57. I. Carmichael, D. M. Chipman, C. A. Podlasek and A. S. Serianni, Torsional Effects on the One-Bond ¹³C-¹³C Spin Coupling Constant in Ethylene Glycol: Insights into the Behavior of ¹J_CC in Carbohydrates. J. Am. Chem. Soc. 1993, 115, 10863.
  
  
• 58. C. Podlasek and A. S. Serianni, ¹⁹F and ¹³C NMR Studies of Polyol Metabolism in Freeze-Tolerant Pupae of Hyalophora cecropia. J. Biol. Chem. 1994, 269, 2521.
  
  
• 59. A. S. Serianni and C. A. Podlasek, ¹³C-¹H Spin-Coupling Constants in Carbohydrates: Magnitude and Sign Determinations via 2-D NMR Methods. Carbohydr. Res. 1994, 259, 277.
  
  
• 60. A. S. Serianni and P. B. Bondo, ¹³C-Labeled D-Ribose: Chemi-Enzymic Synthesis of Various Isotopomers. J. Biomol. Struct. Dyn. 1994, 11, 1133.
  
  
• 61. A. S. Serianni, ¹³C-¹H Spin-Coupling Constants in Furanosyl Rings: Application to Oligonucleotide Structure Determination. In: NMR of Biological Macromolecules, L. Stassinopoulou, ed., NATO ASI Series, 1994, pp. 293-306.
  
  
• 62. J. Wu and A. S. Serianni, [¹³C]-Labeled Oligodeoxyribonucleotides: A Solution Study of a CCAAT-Containing Sequence at the NF-I Recognition Site of Human Adenovirus. Biopolymers 1994, 34, 1175.
  
  
• 63. A. S. Serianni, Stable Isotopically-Labeled Carbohydrates and Nucleosides: Synthesis and Applications in Chemistry and Biology. In: Stable Isotope Applications in Biomolecular Structure and Mechanisms, J. Trewhella, T. A. Cross and C. J. Unkefer, eds., Los Alamos National Laboratory, 1995, pp. 209-245.
  
  
• 64. C. A. Podlasek, J. Wu, W. A. Stripe, P. B. Bondo and A. S. Serianni, [¹³C]-Enriched Methyl Aldopyranosides: Structural Interpretation of ¹³C-¹H Spin-Coupling Constants and ¹H Chemical Shifts. J. Am. Chem. Soc. 1995, 117, 8635.
  
  
• 65. A. S. Serianni and I. Carmichael, One-Bond ¹³C-¹H Spin-Coupling Constants in Aldofuranosyl Rings: Effects of Conformation on Coupling Magnitude. J. Am. Chem. Soc. 1995, 117, 8645.
  
  
• 66. T. Church and A. S. Serianni, Two-bond ¹³C-¹³C Spin-Coupling Constants in Carbohydrates: Effect of Structure on Coupling Magnitude and Sign. Carbohydr. Res. 1996, 280, 177.
  
  
• 67. C. A. Podlasek, W. A. Stripe, I. Carmichael, M. Shang, B. Basu and A. S. Serianni, ¹³C-¹H Spin-Coupling Constants in the beta-D-Ribofuranosyl Ring: Effect of Ring Conformation on Coupling Magnitudes. J. Am. Chem. Soc. 1996, 118, 1413.
  
  
• 68. K. Drew, T. Church, B. Basu, T. Vuorinen and A. S. Serianni, L-[1-¹³C]- and [2-¹³C]Ascorbic Acid: Synthesis and NMR Characterization. Carbohydr. Res. 1996, 284, 135.
  
  
• 69. A. S. Serianni, P.B. Bondo and J. Zajicek, Two-Bond ¹³C-¹³C Coupling Sign Determinations in Carbohydrates: Verification of the Projection Resultant Method. J. Magn. Reson. B 1996, 112, 69.
  
  
• 70. T. Bandyopadhyay, J. Wu, W. A. Stripe, I. Carmichael and A. S. Serianni, ¹³C-¹H and ¹³C-¹³C Spin Couplings in [2'-¹³C]2'-Deoxyribonucleosides: Correlations with Molecular Structure. J. Am. Chem. Soc. 1997, 119, 1737-1744.
  
  
• 71. J. Kennedy, J. Wu, K. Drew, I. Carmichael and A. S. Serianni, Carbohydrate Reaction Intermediates: Effect of Ring Oxygen Protonation on the Structure and Conformation of Aldofuranosyl Rings. J. Am. Chem. Soc. 1997, 119, 8933-8945.
  
  
• 72. T. J. Church, I. Carmichael, and A. S. Serianni, ¹³C-¹H and ¹³C-¹³C Spin-Coupling Constants in Methyl beta-D-Ribofuranoside and Methyl 2-Deoxy-beta-D-erythro-pentofuranoside: Correlation with Molecular Structure and Conformation. J. Am. Chem. Soc. 1997, 119, 8946-8964.
  
  
• 73. K. N. Drew, J. Zajicek, G. Bondo, B. Bose and A. S. Serianni, ¹³C-Labeled Aldopentoses: Detection and Quantitation of Cyclic and Acyclic Forms by 1D and 2D Heteronuclear NMR Spectroscopy. Carbohydr. Res. 1998, 307, 199-209.
  
  
• 74. U. Himmelreich, K. N. Drew, A. S. Serianni and P. W. Kuchel, ¹³C NMR Studies of Vitamin C Transport and Its Redox Cycling in Human Erythrocytes. Biochemistry 1998, 37, 7578-7588.
  
  
• 75. S. Zhao, G. Bondo, J. Zajicek and A. S. Serianni, Two-Bond ¹³C-¹³C Spin-Coupling Constants in Carbohydrates: New Measurements of Coupling Signs. Carbohydr. Res. 1998, 309, 145-152.
  
  
• 76. B. Basu, S. Zhao, P. Bondo, G. Bondo, F. Cloran, I. Carmichael, R. Stenutz, B. Hertz and A. S. Serianni, Three-Bond C-O-C-C Spin-Coupling Constants in Carbohydrates: Development of a Karplus Relationship. J. Am. Chem. Soc. 1998, 120, 11158-11173.
  
  
• 77. W. S. Hays, D. J. VanderJagt, B. Bose, A. S. Serianni and R. H. Glew, Catalytic Mechanism and Specificity for Hydrolysis and Transglycosylation Reactions of Cytosolic beta-Glucosidase from Guinea Pig Liver. J. Biol. Chem. 1998, 273, 34941-34948.
  
  
• 78. A. S. Serianni, Carbohydrate Structure, Conformation and Reactivity: NMR Studies with Stable Isotopes. In: Bioorganic Chemistry: Carbohydrates, S. Hecht, ed., Oxford University Press, 1999, pp. 244-312.
  
  
• 79. F. Cloran, I. Carmichael and A. S. Serianni, ¹³C-¹H and ¹³C-¹³C Spin-Coupling Behavior in Aldofuranosyl Rings from Density Functional Theory. J. Phys. Chem. 1999, A103, 3783-3795.
  
  
• 80. H. Junicke, C. Bruhn, R. Kluge, A. S. Serianni and D. Steinborn, Novel Platinum(IV)-Carbohydrate Complexes: Metal Ion Coordination Behavior of Monosaccharides in Organic Solvents. J. Am. Chem. Soc. 1999, 121, 6232-6241.
  
  
• 81. Z. Hricoviniova-Bilikova, M. Hricovini, M. Petrusova, A. S. Serianni and L. Petrus, Stereospecific Molybdic Acid-Catalyzed Isomerization of 2-Hexuloses to Branched-Chain Aldoses. Carbohydr. Res. 1999, 319, 38-46.
  
  
• 82. R. Stenutz, M. Shang and A. S. Serianni, Methyl beta-Lactoside (methyl 4-O-beta-D-galactopyranosyl-beta-D-glucopyranoside) Methanol Solvate. Acta Cryst. 1999, 55C, 1719-1721.
  
  
• 83. F. Cloran, I. Carmichael and A. S. Serianni, DFT Calculations on Disaccharide Models: Studies of Molecular Geometries and Trans-O-Glycoside ³J_COCH and ³J_COCH Spin-Couplings. J. Am. Chem. Soc. 1999, 121, 9843-9851.
  
  
• 84. F. Cloran, I. Carmichael and A. S. Serianni, ²J_COC Spin-Coupling Constants Across Glycosidic Linkages Exhibit a Valence Bond-Angle Dependence. J. Am. Chem. Soc. 2000, 122, 396-397.
  
  
• 85. H. Junicke, A. S. Serianni and D. Steinborn, Platinum(IV)-Carbohydrate Complexes: Structure Determination Based on ¹H-¹H, ¹³C-¹H and ¹³C-¹³C Spin-Spin Coupling Constants. J. Org. Chem. 2000, 65, 4153-4161.
  
  
• 86. B. Bose-Basu, J. Zajicek, G. Bondo, S. Zhao, M. Kubsch, I. Carmichael, and A. S. Serianni, Deuterium Spin-Lattice Relaxation Times and Quadrupolar Coupling Constants in Isotopically-Labeled Saccharides. J. Magn. Reson. 2000, 144, 207-216.
  
  
• 87. F. Cloran, I. Carmichael and A. S. Serianni, 2-Deoxy-beta-D-erythro-pentofuranosylamine: Quantum Mechanical Calculations of Molecular Structure and NMR Spin-Spin Coupling Constants in Nitrogen-Containing Saccharides. J. Am. Chem. Soc. 2000, 122, 6435-6448.
  
  
• 88. U. Himmelreich, M. Emling, K. N. Drew, A. S. Serianni and P. Kuchel, ¹³C NMR Evidence of the Failure of Human Erythrocytes to Metabolize Ascorbate and Dehydroascorbate to Lactate. Free Radical Bio. Med. 2000, 28, 1607-1610.
  
  
• 89. F. Cloran, I. Carmichael and A. S. Serianni, 2-Deoxy-beta-D-erythro-pentofuranose: Hydroxymethyl Group Conformation and Substituent Effects on Molecular Structure, Ring Geometry and NMR Spin-Spin Coupling Constants from Quantum Chemical Calculations. J. Am. Chem. Soc. 2001, 123, 4781-4791.
  
  
• 90. S. Zhao, L. Petrus and A. S. Serianni, 1-Deoxy-D-Xylulose: Synthesis Based on Molybdate-Catalyzed Rearrangement of a Branched-Chain Aldotetrose. Org. Lett. 2001, 3, 3819-3822.
  
  
• 91. Y. Zhu and A. S. Serianni, Acyclic Forms of [1-¹³C]Aldohexoses in Aqueous Solution: Quantitation by ¹³C NMR and Deuterium Isotope Effects on Tautomeric Equilibria. J. Org. Chem. 2001, 66, 6244-6251.
  
  
• 92. R. Stenutz, I. Carmichael, G. Widmalm and A. S. Serianni, Hydroxymethyl Group Conformation in Saccharides: Structural Dependencies of ²J_HH, ³J_HH and ¹J_CH Spin-Spin Coupling Constants. J. Org. Chem. 2002, 67, 949-958.
  
  
• 93. J. G. Duman and A. S. Serianni, The Role of Endogeneous Antifreeze Protein Enhancers in the Hemolymph Thermal Hysteresis Activity of the Beetle, Dendroides canadensis. J. Insect Physiol. 2002, 48, 103-111.
  
  
• 94. P. A. Voziyan, R. G. Khalifah, C. Thibaudeau, A. Yildiz, J. Jacob, A. S. Serianni and B. G. Hudson, Modification of Proteins In Vitro by Physiological Levels of Glucose. J. Biol. Chem. 2003, 278, 46616-46624.
  
  
• 95. A. S. Serianni and I. Carmichael, ¹³C-¹H and ¹³C-¹³C Scalar Couplings in Isotopically Labeled Mono- Di- and Trisacchaides: NMR and DFT Studies of O-Glycoside and Hydroxymethyl Group Conformation. Polymer Preprints 2003, 44, 319-320.
  
  
• 96. C. Thibaudeau, R. Stenutz, B. Hertz, T. Klepach, S. Zhao, Q. Wu, I. Carmichael and A. S. Serianni, Correlated C-C and C-O Bond Conformations in Saccharide Hydroxymethyl Groups: Parameterization and Application of Redundant ¹H-¹H, ¹³C-¹H and ¹³C-¹³C NMR J-Couplings. J. Am. Chem. Soc. 2004, 126, 15668-15685.
  
  
• 97. T. Klepach, I. Carmichael and A. S. Serianni, Geminal ²J_CCH Spin-Spin Coupling Constants As Probes of the Phi Glycosidic Torsion Angle in Oligosaccharides. J. Am. Chem. Soc. 2005, 127, 9781-9793.
  
  
• 98. Q. Pan, T. E. Klepach, I. Carmichael, M. Reed and A. S. Serianni, ⁴J_COCCH and ⁴J_CCCCH as Probes of Exocyclic Hydroxymethyl Group Conformation in Saccharides. J. Org. Chem. 2005, 70, 7542-7549.
  
  
• 99. V. A. Bennett, T. Sformo, K. Walters, O. Toien, K. Jeannet, R. Hochstrasser, Q. Pan, A. S. Serianni, B. M. Barnes and J. G. Duman, Comparative Overwintering Physiology of Alaska and Indiana Populations of the Beetle Cucujus clavipes (Fabricius): Roles of Antifreeze Proteins, Polyols, Dehydration and Diapause. J. Exp. Biol. 2005, 208, 4467-4477.
  
  
• 100. Q. Pan, B. C. Noll and A. S. Serianni, Methyl 4-O-beta-D-Galactopyranosyl-alpha-D-Glucopyranoside (Methyl alpha-Lactoside). Acta Cryst. 2005, C61, o674-o677.
  
  
• 101. Y. Zhu, Q. Pan, C. Thibaudeau, S. Zhao, I. Carmichael and A. S. Serianni, [¹³C,¹⁵N]2 Acetamido-2-Deoxy-D-Aldohexoses and Their Methyl Glycosides: Synthesis and NMR Investigations of J-Couplings Involving ¹H, ¹³C and ¹⁵N. J. Org. Chem. 2006, 71, 466-479.
  
  
• 102. Q. Pan, B. C. Noll and A. S. Serianni, Methyl 4-O-beta-L-galactopyranosyl-beta-D-glucopyranoside (Methyl beta-L-lactoside). Acta Cryst. 2006, C62, o82-085.
  
  
• 103. N. C. Maiti, Y. Zhu, I. Carmichael, A. S. Serianni and V. E. Anderson, ¹J_CH Correlates with Alcohol Hydrogen Bond Strength. J. Org. Chem. 2006, 71, 2878-2880.
  
  
• 104. Q. Wu, Q. Pan, S. Zhao, H. Imker and A. S. Serianni, A Disaccharide Rearrangement Catalyzed by Molybdate Anion in Aqueous Solution. J. Org. Chem. 2007, 72, 3081-3084.
  
  
• 105. H. Zhao, Q. Pan, W. Zhang, I. Carmichael and A. S. Serianni, Density Functional Theory Calculations and NMR Studies of ²J_COH, ³J_HCOH and ³J_CCOH Spin-Spin Coupling Constants in Saccharides: C-O Torsional Bias and H-Bonding in Aqueous Solution. J. Org. Chem. 2007, 72, 7071-7082. (This article was featured on the cover of this JOC issue.)
  
  
• 106. P. Kline, B. C. Noll, H. Zhao and A. S. Serianni, 1-(beta-D-Erythrofuranosyl)cytidine (beta-erythrocytidine). Acta. Cryst. 2007, C63, o137-o140.
  
  
• 107. B. Basu, T. Klepach, G. Bondo, P. Bondo and A. S. Serianni, ¹³C-¹³C Spin-Spin Coupling Constants in Saccharides: New Correlations with Molecular Structure. J. Org. Chem. 2007, 72, 7511-7522.
  
  
• 108. W. Zhang, B. C. Noll and A. S. Serianni, 3-Deoxy-beta-D-ribo-hexopyranose (3-Deoxy-beta-D-glucopyranose. Acta. Cryst. 2007, C63, o578-o581.
  
  
• 109. S. V. Chetyrkin, W. Zhang, B. G. Hudson, A. S. Serianni and P. A. Voziyan, Pyridoxamine Protects from Functional Damage by 3-Deoxyglucosone: Mechanism of Action of Pyridoxamine. Biochemistry 2008, 47, 997-1006.
  
  
• 110. T. Klepach, I. Carmichael and A. S. Serianni, ¹³C-¹H and ¹³C-¹³C NMR J-Couplings in ¹³C-Labeled N-Acetyl-neuraminic Acid: Correlations with Molecular Structure. J. Org. Chem. 2008, 73, 4376-4387.
  
  
• 111. H. Zhao, I. Carmichael and A. S. Serianni, Oligosaccharide Trans-Glycoside ³J_COCC Karplus Curves Are Not Equivalent: Effect of Internal Electronegative Substituents. J. Org. Chem. 2008, 73, 3255-3257.
  
  
• 112. U. Olsson, A. S. Serianni and R. Stenutz, Conformational Analysis of beta-Glycosidic Linkages in ¹³C-Labeled Glucobiosides Using Inter-residue Scalar Coupling Constants. J. Phys. Chem. B 2008, 112, 4447-4453.
  
  
• 113. T. Klepach, G. Bondo and A. S. Serianni, ¹³C-Labeled N-Acetyl-neuraminic Acid in Aqueous Solution: Detection and Quantification of Acyclic Keto and Enol Forms by ¹³C NMR. J. Am. Chem. Soc. 2008, 130, 11892-11900.
  
  
• 114. L. Sweet, W. Zhang, H. Torres-Fewell, A. S. Serianni, W. Boggess and J. Schorey, Mycobacterium avium Glycopeptidolipids Require Specific Acetylation and Methylation Patterns For Signaling Through TLR2. J. Biol. Chem. 2008, 283, 33221-33231.
  
  
• 115. K. R. Walters, Jr., Q. Pan, A. S. Serianni and J. G. Duman, Cryoprotectant Biosynthesis and the Selective Accumulation of Threitol in the Freeze-tolerant Alaskan Beetle, Upis ceramboides. J. Biol. Chem. 2009, 284, 16822-16831.
  
  
• 116. W. Zhang, H. Zhao, I. Carmichael and A. S. Serianni, An NMR Investigation of Putative Inter-residue H-Bonding in Methyl alpha-Cellobioside in Solution. Carbohydr. Res. 2009, 344, 1582-1587.
  
  
• 117. T. Klepach, M. Reed, B. C. Noll, A. G. Oliver and A. S. Serianni, Methyl beta-Allolactoside [Methyl beta-D-Galactopyranosyl-(1,6)beta-D-glucopyranoside] Monohydrate. Acta Cryst. 2009, C65, o601-o606. (This article was featured on the cover of this Acta issue.)
  
  
• 118. K. R. Walters, A. S. Serianni, T. Sformo, B. M. Barnes and J. G. Duman, A Non-protein Thermal Hysteresis-producing Xylomannan Antifreeze in the Freeze-Tolerant Alaskan Beetle, Upis ceramboides. Proc. Natl. Acad. Sci. 2009, 106, 20210-20215.
  
  
• 119. A. S. Serianni, X. Hu and I. Carmichael, Side-Chain Conformations as Mediators of Saccharide Structure and Function: N-Acyl Groups in Aminosugars. Glycoconjugate Journal 2009, 26, 805 (20th International Symposium on Glycoconjugates, Program/Abstract No. 19).
  
  
• 120. X. Hu, Q. Pan, B. C. Noll, A. G. Oliver and A. S. Serianni, Methyl 4-O-beta-D-Galactopyranosyl-alpha-D-Mannopyranoside, Methanol 0.375-Solvate. Acta Cryst. 2010, C66, o67-o70.
  
  
• 121. X. Hu, W. Zhang, I. Carmichael and A. S. Serianni, Amide Cis-Trans Isomerization in Aqueous Solutions of N-Formyl-D-Glucosaminides and N-Acetyl-D-Glucosaminides: Chemical Equilibria and Exchange Kinetics. J. Am. Chem. Soc. 2010, 132, 4641-4652.
  
  
• 122. P. C. Kline, H. Zhao, B. C. Noll, A. G. Oliver, and A. S. Serianni, 1-(beta-D-Erythrofuranosyl)adenosine (beta-Erythroadenosine). Acta Cryst. 2010, C66, o215-o218.
  
  
• 123. X. Hu, I. Carmichael and A. S. Serianni, N-Acetyl Side-Chains in Saccharides: NMR J-Coupling Equations Sensitive to CH-NH and NH-CO Bond Conformations in 2-Acetamido-2-Deoxy-Aldohexopyranosyl Rings. J. Org. Chem. 2010, 75, 4899-4910.
  
  
• 124. W. Zhang, A. G. Oliver and A. S. Serianni, 4-Deoxy-4-fluoro-beta-D-ribo-hexopyranose. Acta. Cryst. 2010, C66, o496-o498.
  
  
• 125. W. Zhang, A. G. Oliver and A. S. Serianni, Methyl 4-O-beta-D-galactopyranosyl-beta-D-allopyranoside tetrahydrate. Acta. Cryst. 2010, C66, o484-487.
  
  
• 126. W. Zhang, A. G. Oliver and A. S. Serianni, Co-crystals of 3-deoxy-3-fluoro-alpha-D-glucopyranose and 3-deoxy-3-fluoro-beta-D-glucopyranose. Acta Cryst. 2010, C66, o557-o560.
  
  
• 127. K. R. Walters, A. S. Serianni, Y. Voituron, T. Sformo, B. M. Barnes and J. G. Duman, A Thermal Hysteresis-Producing Xylomannan Glycolipid Antifreeze Associated with Cold Tolerance Is Found In Diverse Taxa. J. Comp. Physiol. B 2011, 181, 631-640.
  
  
• 128. X. Hu, W. Zhang, A. G. Oliver and A. S. Serianni, Methyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside dihydrate and methyl 2-formamido-2-deoxy-alpha-D-glucopyranoside. Acta Cryst. 2011, C67, o146-o150.
  
  
• 129. W. Zhang, I. Carmichael and A. S. Serianni, Rearrangement of 3-Deoxy-D-erythro-hexos-2-ulose in Aqueous Solution: NMR Evidence of 1,2-Hydrogen Transfer. J. Org. Chem. 2011, 76, 8151-8158.
  
  
• 130. W. Zhang, A.G. Oliver and A.S. Serianni, Disorder and Conformational Analysis of Methyl beta-D-Galactopyranosyl-(1,4)-beta-D-Xylopyranoside. Acta. Cryst. 2012, C68, o7-o11.
  
  
• 131. B. M. Sattelle, B. Bose-Basu, M. Tessier, R. J. Woods, A. S Serianni and A. Almond, Dependence of Pyranose Ring Puckering on Anomeric Configuration: Methyl Idopyranosides. J. Phys. Chem. B 2012, 116, 6380-6386.
  
  
• 132. W. Zhang and A. S. Serianni, Phosphate-Catalyzed Degradation of D-Glucosone in Aqueous Solution Is Accompanied By C1-C2 Transposition. J. Am. Chem. Soc. 2012, 134, 11511-11524.
  
  
• 133. W. Zhang, X. Hu, I. Carmichael and A. S. Serianni, Methyl [¹³C] Glucopyranosiduronic Acids: Effect of COOH Ionization and Exocyclic Structure on NMR Spin-Couplings. J. Org. Chem. 2012, 77, 9521-9534.
  
  
• 134. W. Zhang, A. G. Oliver, H. M. Vu, J. G. Duman and A. S. Serianni, Methyl 4-O-beta-D-mannopyranosyl-beta-D-xylopyranoside. Acta Cryst. 2012, C68, o502-o506.
  
  
• 135. W. Zhang, A. G. Oliver, H. M. Vu, J. G. Duman and A. S. Serianni, Methyl 4-O-beta-D-xylopyranosyl-beta-D-mannopyranoside, a Core Disaccharide of an Antifreeze Glycolipid. Acta Cryst. 2013, C69, 1047-1050.
  
  
• 136. D. J. Larson, L. Middle, H. Vu, W. Zhang, A. S. Serianni, J. Duman and B. M. Barnes, Wood Frog Adaptations to Overwintering in Alaska: New Limits to Freezing Tolerance. J. Exp. Biol. 2014, 217, 2193-2200.
  
  
• 137. T. Klepach, H. Zhao, X. Hu, W. Zhang, R. Stenutz, M. J. Hadad, I. Carmichael and A. S. Serianni, Informing Saccharide Structural NMR Studies with Density Functional Theory Calculations. In: Methods in Molecular Biology 1273 – Glycoinformatics, T. Lütteke and M. Frank, eds., Springer, New York, 2015, pp. 289-331.
  
  
• 138. W. Zhang, S. Zhao and A. S. Serianni, Labeling Monosaccharides With Stable Isotopes, Methods in Enzymology, 2015, in press.
  
  
• 139. B. Bose-Basu, W. Zhang, J. L. W. Kennedy, M. J. Hadad, I. Carmichael and A. S. Serianni, ¹³C-Labeled Idohexopyranosyl Rings: Effects of Methyl Glycosidation and C6 Oxidation on Ring Conformational Equilibria, Journal of Organic Chemistry. Submitted.
  
  
• 140. W. Zhang and A. S. Serianni, On the Stability of D-Glucose in Aqueous Phosphate Buffer: A ¹³C NMR Investigation With Singly ¹³C-Labeled Isotopomers. In Preparation.
  
  
• 141. H. Zhao, I. Carmichael, M. J. Hadad and A. S. Serianni, Vicinal ¹³C-¹³C NMR Spin-Coupling Constants in Oligosaccharides: Generalized Equations for O-Glycosidic Linkage Conformational Analysis. In Preparation.
  
  
• 142. H. Zhao, I. Carmichael and A. S. Serianni, Detection and Quantification of Hydrogen Bonding in Saccharides Through Functional NMR J-Couplings. In Preparation.