Deuterium isotope effects in carbohydrates revisited. Cryoprobe studies of the anomerization and NH to ND deuterium isotope induced 13C NMR chemical shifts of acetamidodeoxy and aminodeoxy sugars.
Complete 1H and 13C NMR chemical shift assignments have been generated from a series of acetamidodeoxy and aminodeoxy sugar derivatives. For free sugars, the enhanced sensitivity of an NMR cryoprobe allowed simple 1D and 2D NMR spectra to be obtained from essentially single anomers, before significant mutarotation had occurred. The NMR assignments have been used to characterize deuterium isotope effects on 13C chemical shifts measured under conditions of slow NH to ND exchange in single solutions. Within a range of 0 to -0.138 ppm, beta, gamma, delta, and zeta deuterium isotope effects have been observed, thus providing additional reference data for assignment of the 13C NMR spectra of nitrogenous saccharides.
Coxon
Bruce
B
National Institute of Child Health and Human Development, 31 Center Drive, MSC 2423, National Institutes of Health, Bethesda, MD 20892, USA. coxonb@mail.nih.gov
D000586:Amination; D002241:Carbohydrates / Q000737:chemistry*; D002247:Carbon Isotopes; D003903:Deuterium / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D015335:Molecular Probes / Q000032:analysis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry
D002241:Carbohydrates; D002247:Carbon Isotopes; D015335:Molecular Probes; D003903:Deuterium; D009584:Nitrogen; D010100:Oxygen