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Two-dimensional 1H-, 13C-, and 31P-nuclear magnetic resonance and molecular-mechanics investigation of d-fructose 2,6-bisphosphate

✍ Scribed by Ronald J. Voll; Subbaraya Ramaprasad; David Vargas; Ezzat S. Younathan; Saad Laban; Theodore A.W. Koerner

Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
677 KB
Volume
203
Category
Article
ISSN
0008-6215

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✦ Synopsis

Two-dimensional nuclear magnetic resonance studies have been carried out to assign unequivocally all the proton, carbon, and phosphorus resonances of D-fCUCtOfUranO%z 2,bbisphosphate

(1) and to verify its structure using a 400-MHz spectrometer. Several unexpected chemical-shift values and coupling constants were obtained. Molecular mechanics calculations (Sybyl) carried out to minimize the conformational energy of 1 yield (~c_,,r_~ = + 84, ~)c_,,r_~ = -155, and ercs,r._6 = + 175". Thus the unusual near-gauche orientations of C-l and C-3 to F-2 in 1 can explain their small vicinal coupling constants (3Jc_,p_I = 1.2, and '.Jc.,,,, = 3.8 Hz), in contrast to the expected larger value seen for 3Jc_5.p4 namely, 6.9 Hz. Treatment of a sample of this compound with sodium borohydride did not affect its nuclear magnetic resonance spectrum, substantiating that O-2 is phosphorylated. Oxidation with sodium periodate yielded an intermediate which decomposed by a p-elimination mechanism involving the 6-phosphate group. These data establish unequivocally the 'H, "C, and "P assignments and explain the observed anomalous shifts. Moreover they indicate that the activator of fructose 6-phosphate I-kinase is the j? anomer of the 4T, conformer of D-fructose 2,6-bisphosphate.

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