Nuclear Magnetic Resonance Spectroscopy of Monosaccharides

CARBON-13 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF MONOSACCHARIDES... 

K. Bock and C. Pedersen, Carbon-13 nuclear magnetic resonance spectroscopy of monosaccharides, Adv. Carbohydr. Chem. Biochem., 41 (1983) 27-66. 

Walker, T. E., R. E. London, T. W. Whaley, R. Barker, and N. A. Matwiyoff Carbon-13 Nuclear Magnetic Resonance Spectroscopy of (1- C) Enriched monosaccharides. Signal Assignments and orientation dependance of geminal and vicinal Carbon-Carbon and Carbon-Hydrogen Spin-Spin coupling constants. J. Amer. Chem. Soc. 98,5807 (1976) and references cited therein. 

Monomer (Section 6 21) The simplest stable molecule from which a particular polymer may be prepared Monosaccharide (Section 25 1) A carbohydrate that cannot be hydrolyzed further to yield a simpler carbohydrate Monosubstituted alkene (Section 5 6) An alkene of the type RCH=CH2 in which there is only one carbon directly bonded to the carbons of the double bond Multiplicity (Section 13 7) The number of peaks into which a signal IS split in nuclear magnetic resonance spectroscopy Signals are described as singlets doublets triplets and so on according to the number of peaks into which they are split... 

Vliegenthart JFG, Borland L, van Halbeek H. High-resolution nuclear magnetic resonance spectroscopy as a tool in the structural analysis of carbohydrates related to glycoproteins. Adv Carbohydr Chem Biochem 1983 41 209-374. Bock K, Pedersen C. Carbon-13 nuclear magnetic resonance of monosaccharides. Adv Carbohydr Chem Biochem 1983 41 27-66. 

The discovery of enzymes that could selectively break down hyaluronan opened the door for the establishment of the polysaccharide molecule s chemical structure. In those days, a powerful tool for analysing the structure of polysaccharides such as nuclear magnetic resonance spectroscopy NMR was not known. At the present time, NMR makes it possible to determine the monosaccharide biopolymer residue s composition, centres for substitution reactions, sequence and three-dimensional structure. 

The composition of isomers in aqueous solution, after equilibrium is reached, is compiled for a number of monosaccharides in Table 4.6. Evidence for such compositions is obtained by polarimetry, by oxidation with bromine, which occurs at a much higher reaction rate with P- than a-pyranose and, above all, by nuclear magnetic resonance spectroscopy ( H-NMR). 

The next chapter, by Ren Csuk and Brigitte I. Glanzer (Zdrich), constitutes an extensive treatise on the nuclear magnetic resonance (n.m.r.) spectroscopy of fluorinated monosaccharides [whose early chemistry was surveyed in Vol. 38 (1981) by Anna A. E. Penglis] the comprehensive data tabulated herein should be especially of value to those working in the fleld. It continues the coverage, in Advances, of n.m.r. spectroscopy as the key tool for characterization of carbohydrates. It complements articles on the H-n.m.r. spectroscopy of carbohydrates by Laurance D. Hall [Vols. 19 (1964) and 29 (1974)], Bruce Coxon [Vol. 27 (1972)], and Johannes F. G. Vliegenthart, Lambertus Dorland, and Herman van Halbeek [Vol. 41 (1983)], and on the C-n.m.r. spectroscopy of monosaccharides by Klaus Bock and Christian Pedersen [Vol. 41... 

Nuclear magnetic resonance (NMR) spectroscopy is a very powerful tool for analyzing the conformation and molecular architecture of carbohydrate molecules. Both one- and two-dimensional (ID and 2D) methodologies have provided valuable information about small and large molecules, ranging from the anomeric configuration of a monosaccharide to the sequence of monosaccharide residues that constitute an oligo- or polysaccharide. 

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