Garrett E C, Serianni A S
Department of Chemistry and Biochemistry, University of Notre Dame, IN 46556.
Carbohydr Res. 1990 Dec 15;208:23-35. doi: 10.1016/0008-6215(90)80082-e.
(1-13C)Glycerol, D-(1-13C)arabinitol, D-(1-13C)ribitol, D-(1-13C)xylitol, D-(1-13C)glucitol, D-(1-13C)mannitol, and D-(1-13C)talitol have been prepared by NaBH4 reduction of the corresponding (1-13C)aldoses. A comparison of the 1H- (300 and 620 MHz) and 13C (75 MHz) n.m.r. spectra of natural and (1-13C)-substituted dissymmetric alditols has permitted the unequivocal assignments of their hydroxymethyl proton and carbon signals and the measurement of several 13C-1H and 13C-13C spin-coupling constants. Similar spectra of (1-13C)-substituted symmetric alditols, however, are more difficult to interpret since they are composed of overlapping 13C-coupled and 13C-noncoupled subspectra. In some cases, 1H difference spectra and 1H-coupled 13C spectra may be used to extract the 13C-1H and 13C-13C spin couplings from the 13C-coupled component. These couplings have been examined in light of conformational models previously proposed, permitting a preliminary evaluation of standard 3JCH and 3JCC values for specific coupling pathways in these compounds.
(1-¹³C)甘油、D-(1-¹³C)阿拉伯糖醇、D-(1-¹³C)核糖醇、D-(1-¹³C)木糖醇、D-(1-¹³C)葡萄糖醇、D-(1-¹³C)甘露醇和D-(1-¹³C)艾杜醇已通过用硼氢化钠还原相应的(1-¹³C)醛糖制得。对天然的和(1-¹³C)取代的不对称糖醇的¹H-（300和620兆赫）及¹³C（75兆赫）核磁共振谱进行比较，使得能够明确归属它们的羟甲基质子和碳信号，并测量了几个¹³C-¹H和¹³C-¹³C自旋耦合常数。然而，(1-¹³C)取代的对称糖醇的类似谱更难解释，因为它们由重叠的¹³C耦合和¹³C非耦合子谱组成。在某些情况下，¹H差值谱和¹H耦合的¹³C谱可用于从¹³C耦合组分中提取¹³C-¹H和¹³C-¹³C自旋耦合。已根据先前提出的构象模型对这些耦合进行了研究，从而能够对这些化合物中特定耦合途径的标准³JCH和³JCC值进行初步评估。
