title: Labeling monosaccharides with stable isotopes.
abstract: Chemical and chemi-enzymic methods are discussed for the preparation of monosaccharide isotopomers that are singly and multiply labeled with (13)C, (2)H, (17/18)O, and (15)N isotopes. The discussion focuses primarily on chemical methods to incorporate stable isotopes into monosaccharides and not on methods to assemble labeled monosaccharides into more complex biomolecules such as oligosaccharides or oligonucleotides. Two primary isotope insertion reactions are considered: cyanohydrin reduction (CR) and molybdate-catalyzed epimerization (MCE). Both methods are described in detail, including discussions of their mechanistic features, and their advantages and limitations. The integration of CR, MCE, and other chemical synthetic processes with enzyme-mediated synthesis is also discussed to illustrate how a wide range of singly and multiply labeled monosaccharides can be prepared for subsequent use in the assembly of more complex isotopically labeled biomolecules.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, USA.
authors.forename: Wenhui
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Omicron Biochemicals, Inc., South Bend, Indiana, USA.
authors.forename: Shikai
authors.initials: S
authors.lastname: Zhao
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, USA. Electronic address: aseriann@nd.edu.
authors.forename: Anthony S
authors.initials: AS
authors.lastname: Serianni
mesh_terms: D007553:Isotope Labeling; D009005:Monosaccharides / Q000737:chemistry*
chemical_list: D009005:Monosaccharides
keywords: (13)C-labeled sugars; Chemi-enzymic synthesis of labeled saccharides; Cyanohydrin reduction; Deuterium-labeled sugars; Isotopically labeled 2-ketoses; Isotopically labeled aldoses; Molybdate-catalyzed epimerization of aldoses; Multiply labeled monosaccharides; Oxygen-labeled sugars; Singly labeled monosaccharides