Literature: Labeled Saccharides - Omicron Biochemicals, Inc.

	Literature: Labeled Saccharides

Stable isotopically-labeled carbohydrates have been used to address a wide range of chemical and biological problems. The following is a list of literature references to investigations conducted by the Omicron group that illustrate some applications of labeled compounds.

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 6, 1977, 535.
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. 72, 1979, 71.
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. 72, 1979, 79.
A. S. Serianni, J. Pierce and R. Barker, Carbon-13 Enriched Carbohydrates: Preparation of Triose, Tetrose and Pentose Phosphates, Biochemistry 18, 1979, 1192.
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. 57, 1979, 3160.
A. S. Serianni, H. A. Nunez and R. Barker, The Cyanohydrin Synthesis: Studies with [¹³C]Cyanide, J. Org. Chem. 45, 1980, 3329.
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. 100, 1982, 87.
A. S. Serianni and R. Barker, ¹³C Spin-Lattice Relaxation Times of [1-¹³C]-Enriched Carbohydrates, J. Magn. Reson. 49, 1982, 335.
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. 104, 1982, 4037.
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. 104, 1982, 6764.
R. Barker, H. A. Nunez, P. Rosevear and A. S. Serianni, ¹³C NMR Analysis of Complex Carbohydrates, Methods in Enzymology 83, V. Ginsburg. Ed., 1982, 58.
A. S. Serianni, H. A. Nunez, M. L. Hayes and R. Barker, Chemical Synthesis of Monosaccharides Enriched with Carbon Isotopes, Methods in Enzymology 89, Part D, W. Wood, Ed., 1982, 64.
A. S. Serianni, J. Pierce and R. Barker, Chemical Synthesis of Aldose Phosphates Enriched with Carbon Isotopes, Methods in Enzymology 89, Part D, W. Wood, Ed., 1982, 73.
A. S. Serianni, E. L. Clark and R. Barker, Chemical Synthesis of Aldoses Enriched with Isotopes of Hydrogen and Oxygen, Methods in Enzymology 89, Part D, W. Wood, Ed., 1982, 79.
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 89, Part D, W. Wood, Ed., 1982, 83.
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.
G. Wu, A. S. Serianni and R. Barker, Stereospecific Exchange of Methylene Protons in Tetrofuranosides: Hydroxymethyl Group Conformations in Pentofuranosides, J. Org. Chem. 48, 1983, 1750.
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. 49, l984, 3292.
J. Pierce, A. S. Serianni and R. Barker, Anomerization of Furanose Sugars and Sugar Phosphates, J. Am. Chem. Soc. 107, 1985, 2448.
R. Barker and A. S. Serianni, Carbohydrates In Solution: Studies With Stable Isotopes, Acc. Chem. Res. 19, 1986, 307.
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. 154, 1986, 29.
J. R. Snyder and A. S. Serianni, D-Idose: A One- and Two- Dimensional NMR Investigation of Solution Composition and Conformation, J. Org. Chem. 51, 1986, 2694.
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.
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. 163, 1987, 169.
J. R. Snyder and A. S. Serianni, Stable Isotopically-Enriched DL- Apiose: Synthesis, NMR Analysis and Furanose Anomerization, Carbohydr. Res. 166, 1987, 85.
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. 109, 1987, 4464.
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. 109, 1987, 3501.
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. 109, 1987, 5297.
P. C. Kline and A. S. Serianni, Chiral Hydroxymethyl Groups: ¹H NMR Assignments of the Prochiral C5' Protons of Ribonucleosides, Magnetic Resonance in Chemistry 26, 1988, 120.
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. 175, 1988, 49.
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 158, 1988, 175.
J. R. Snyder and A. S. Serianni, Furanose Ring Anomerization: A Kinetic Study of the 5-Deoxy-pentoses and 5-O-Methylpentoses, Carbohydr. Res. 184, 1988, 13.
J. R. Snyder, E. R. Johnston and A. S. Serianni, Talose Anomerization: NMR Methods to Evaluate the Reaction Kinetics, J. Am. Chem. Soc. 111, 1989, 2681.
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 158, 1989, 661.
P. C. Kline and A. S. Serianni, Chiral Hydroxymethyl Groups: ¹H NMR Assignments of the Prochiral C5' Protons of 2'- Deoxyribonucleosides, Magnetic Resonance in Chemistry 28, 1990, 324.
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. 112, 1990, 5886.
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. 112, 1990, 7373.
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. 9, 1990, 513.
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.
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. 206, 1990, 1.
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. 206, 1990, 183.
T. Vuorinen and A. S. Serianni, [¹³C]-Substituted Pentos-2-uloses: Synthesis and Analysis by ¹H and ¹³C NMR Spectroscopy, Carbohydr. Res. 207, 1990, 185.
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. 208, 1990, 23.
U. L. Stafford, A. S. Serianni and A. Varma, Microcomputer Automated Synthesis of Stable Isotopically Labeled Monosaccharides, American Institute of Chemical Engineering Journal 36, 1990, 1822.
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. 68, 1990, 2171.
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. 209, 1990, 13.
J. R. Snyder and A. S. Serianni, Deoxygenated and Alkylated Furanoses: Thorpe-Ingold Effects on Tautomeric Equilibria and Rates of Anomerization, Carbohydr. Res. 210, 1991, 21.
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. 210, 1991, 51.
J. Wu and A. S. Serianni, Ring-Opening Kinetics of the D- Pentofuranuronic Acids, Carbohydr. Res. 211, 1991, 207.
J. Wu and A. S. Serianni, Isotope-Edited 1D and 2D NMR Spectroscopy of [¹³C]-Substituted Carbohydrates, Carbohydr. Res. 226, 1992, 209.
P. C. Kline and A. S. Serianni, [¹³C]-Substituted Erythronucleosides: Synthesis and Conformational Analysis by ¹H and ¹³C NMR Spectroscopy, J. Org. Chem. 57, 1992, 1772.
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. 114, 1992, 3499.
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.
J. Wu, P. B. Bondo and A. S. Serianni, Multiply ¹³C-Substituted Monosaccharides: Synthesis of D-[1,5,6-¹³C₃]Glucose and D-[2,5,6-¹³C₃]Glucose, Carbohydr. Res. 226, 1992, 261.
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. 58, 1993, 5513.
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. 249, 1993, 281.
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. 115, 1993, 10863.
C. Podlasek and A. S. Serianni, ¹⁹F and ¹³C NMR Studies of Polyol Metabolism in Freeze-Tolerant Pupae of Hyalophora cecropia, J. Biol. Chem. 269, 1994, 2521.
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. 259, 1994, 277.
A. S. Serianni and P. B. Bondo, ¹³C-Labeled D-Ribose: Chemi- Enzymic Synthesis of Various Isotopomers, J. Biomol. Struct. Dyn. 11, 1994, 1133.
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.
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 34, 1994, 1175.
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.
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. 117, 1995, 8635.
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. 117, 1995, 8645.
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. 280, 1996, 177.
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. 118, 1996, 1413.
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. 284, 1996, 135.
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. Series B 112, 1996, 69.
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. 119, 1997, 1737-1744.
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. 119, 1997, 8933-8945.
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. 119, 1997, 8946-8964.
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. 307, 1998, 199-209.
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 37, 1998, 7578-7588.
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. 309, 1998, 145-152.
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. 120, 1998, 11158-11173.
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. 273, 1998, 34941-34948.
A. S. Serianni, Carbohydrate Structure, Conformation and Reactivity: NMR Studies with Stable Isotopes, in Bioorganic Chemistry: Carbohydrates, S. Hecht, ed., Oxford University Press, 1999.
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. A103, 1999, 3783-3795.
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. 121, 1999, 6232-6241.
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.
R. Stenutz, M. Shang and A.S. Serianni, Methyl beta-Lactoside (methyl 4-O-beta-D-galactopyranosyl-beta-D-glucopyranoside) Methanol Solvate, Acta Cryst. 55C, 1999, 1719-1721.
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.
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.
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.
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.
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.
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.
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, in press.
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 and Conformational Equilibria, submitted.
S. Zhao, L. Petrus and A.S. Serianni, 1-Deoxy-D-Xylulose: A Concise Synthesis Based on Molybdate-Catalyzed Rearrangement of a Branched-Chain Aldotetrose, submitted.