Structures and sites of nonenzymatic glucosylation of protein: characterization by carbon-13 nuclear magnetic resonance spectroscopy

Thesis/Dissertation · Tue Jan 01 00:00:00 EST 1985

OSTI ID:5531645

Fisher, C I

Products of nonenzymatic glucosylation of protein were studied by carbon-13 NMR spectroscopy at 100 MHz in phosphate buffer. The anomeric region of the spectrum of glycated cytochrome c (blocked amino terminus) showed three signals representing the C-2 carbon of the alpha and beta-furanose (101.7 and 99.2 ppm) and beta pyranose (95.8 ppm) anomers of the Amadori rearrangement products (ARP) at lysine epsilon amino groups. The spectrum of glycated poly-L-lysine showed two distinct sets of three resonances; the second set, resonating to lower shielding than the first, was assigned to C-2 of the anomers of ARP at the alpha amino terminus. A third set of peaks was observed on glucation of RNase A corresponding to the ARP at lysine residue 41. The anomeric region of RNase denatured with urea at pH 7.4 was similar to that of glycated poly-L-lysine, while at pH 4.0 it was indistinguishable from that of glycated cytochrome c. The anomeric spectum of glycated hemoglobin was comparable to that of poly-L-lysine, and distinct resonances were observed for the ARP at the alpha amino terminal valine and epsilon amino groups. Because of the differences in chemical shift of C-2 of the ARP, we conclude that the pKa of the amino group influences the electronic environment of the anomeric carbon of the ARP.

• Research Organization: South Carolina Univ., Columbia (USA)
• OSTI ID: 5531645
• Resource Relation: Other Information: Thesis (Ph. D.)
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
PROTEINS
NUCLEAR MAGNETIC RESONANCE
CARBON 13
CYTOCHROMES
LYSINE
METABOLISM
PHOSPHATES
TRACER TECHNIQUES
AMINO ACIDS
CARBON ISOTOPES
CARBOXYLIC ACIDS
EVEN-ODD NUCLEI
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHORUS COMPOUNDS
PIGMENTS
RESONANCE
STABLE ISOTOPES
550201* - Biochemistry- Tracer Techniques