Synthesis and structure determination of [8(-13)C]guanosine 5'-diphosphate.
A combined chemical and enzymatic synthesis of [8(-13)C]guanosine 5'-diphosphate (GDP) from H13COOH is described. About 35 mg nucleotide was obtained from 500 mg H13COOH. Analysis of the [8(-13)C]GDP by negative ion fast atom bombardment mass spectrometry and by 13C NMR confirmed that one atom of 13C was incorporated at the 8-position of the guanine ring at 90 +/- 10% enrichment. The chemical shift of the C(8) was 140.2 ppm downfield from internal trimethylsilylpropionate at neutral pH and room temperature, with a spin-spin coupling 1J(13C(8)-H(8] of 217 Hz and a 3J(13C(8)-H(1'] of 3.9 Hz.
Poe
M
M
Department of Biophysics, Merck Sharp & Dohme Research Laboratoires, Rahway, New Jersey 07065.
Germershausen
J I
JI
MacCoss
M
M
D002247:Carbon Isotopes; D002851:Chromatography, High Pressure Liquid; D006150:Guanine Nucleotides / Q000138:chemical synthesis*; D006153:Guanosine Diphosphate / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D002247:Carbon Isotopes; D006150:Guanine Nucleotides; D006153:Guanosine Diphosphate