1978
DOI: 10.1139/v78-508
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A conformational study of methyl β-cellobioside-d8 by 13C nuclear magnetic resonance spectroscopy: dihedral angle dependence of 3JC–H in 13C—O—C—1H arrays

Abstract: Methyl β-cellobioside (2) has been deuterated at positions C-2, -3, -3′, -4, -6, and -6′ by 1H–2H exchange with deuterium oxide in the presence of Raney nickel catalyst. The resulting simplification in the 13C nmr spectrum of this isotopically-labelled compound has facilitated the measurement of interresidue 13C–1H coupling, as a means of determining the orientation of the glycosidic linkage in 2. Three-bond coupling across the linkage between 13C-4′ and H-1 is found to be 4.3 Hz and that between 13C-4′ and H-… Show more

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Cited by 107 publications
(41 citation statements)
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“…The 4 and y angles (44.6, -13.7) found for crystalline cellobiose 1561 also fall within the range marked in Fig. 8, closer to the former of the two minima, whereas conformational analysis of methyl P-('H8)cellobioside based on interglycosidic 'Hi' 3C coupling constants gave 4, y values within the range 25 -30" for both of these angles [57]; these values would agree better with a conformation that is dynamically averaged between the two conformational states indicated in Fig. 8.…”
Section: Calculated With Eqn Rij = R K L ( O K L / O T J ) 1 'supporting
confidence: 60%
“…The 4 and y angles (44.6, -13.7) found for crystalline cellobiose 1561 also fall within the range marked in Fig. 8, closer to the former of the two minima, whereas conformational analysis of methyl P-('H8)cellobioside based on interglycosidic 'Hi' 3C coupling constants gave 4, y values within the range 25 -30" for both of these angles [57]; these values would agree better with a conformation that is dynamically averaged between the two conformational states indicated in Fig. 8.…”
Section: Calculated With Eqn Rij = R K L ( O K L / O T J ) 1 'supporting
confidence: 60%
“…1D and 2D 1 H/ 15 N heteronuclear single quantum, multiple bond correlation (HSQMBC) NMR spectra33 , 34 were acquired by using a Bruker hsqcetf3gpjclrnd pulse sequence, which included shaped, 180° chirp pulses of 500 μs and 2 ms for inversion and refocusing, respectively, at the 15 N frequency. A pulse sequence execution error in the form of nonprogressive accumulation of data was eliminated by setting separate, but equal phase programs (ph14 = 0 0 0 0 2 2 2 2 and ph4 = 0 0 0 0 2 2 2 2) for the shaped 15 N refocusing pulse and the following 15 N 90° high power pulse, respectively. The 1/2J delay was calculated from 1 J NH 93 Hz, whereas the evolution delay for long-range 1 H-15 N coupling constants was 83 ms. 1D HSQMBC was conducted by using 16384 point data sets, linearly predicted to 65536 points.…”
Section: Nmr Spectroscopymentioning
confidence: 99%
“…Measurement of the coupling constants was performed by 1D 1 H NMR of 15 N-labeled amino sugars30 , 31 , 36 -38 and/or 1D and 2D 1 H/ 15 N HSQMBC33 , 34 of amino sugars having 15 N either enriched or at natural abundance. The latter experiments were facilitated by the enhanced sensitivity of a 1 H/ 13 C/ 15 N inverse NMR cryoprobe which yielded excellent HSQMBC spectra from 1 mg of 15 N-labeled derivative, or from 20-30 mg having 15 N at natural abundance.…”
Section: Multinuclear Nmr Data and Molecular Dynamicsmentioning
confidence: 99%
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