Makarieva Tatyana N, Shubina Larisa K, Guzii Alla G, Ivanchina Natalya V, Denisenko Vladimir A, Afiyatullov Shamil S, Dmitrenok Pavel S, Kalinovsky Anatoly I, Stonik Valentin A
Pacific Institute ofBioorganic Chemistry, FEB RAS, pr. 100 let Vladivostoku, 159, Vladivostok 690022, Russian Federation.
Nat Prod Commun. 2011 May;6(5):673-6.
A study has been made of the 1H NMR spectra of peracetylated beta-glucopyranosides and alpha-arabinopyranosides obtained by reaction of D- and L-glucoses, and L- and D-arabinoses with either (R)- or (S)-2-octanols. The obtained and literature data show that 1H NMR spectra may be used to determine the absolute configuration of the aglycone moieties of some alicyclic glycosides without the need to synthesize derivatives with chiral reagents, as long as the absolute configuration of their monosaccharide moiety is known or vice versa. Spectra of marine steroid glycosides and their acetates containing glycosylated side chains as alicyclic fragments were also examined. It was shown that analysis of 1H NMR spectra for the determination of the absolute configuration is more applicable in the cases when glycosides have the same substitution in the D-ring of the aglycone moiety.
对通过 D-和 L-葡萄糖以及 L-和 D-阿拉伯糖与 (R)-或 (S)-2-辛醇反应得到的全乙酰化β-吡喃葡萄糖苷和α-吡喃阿拉伯糖苷的 1H NMR 光谱进行了研究。所获得的数据以及文献数据表明，只要已知单糖部分的绝对构型，或者反之亦然，1H NMR 光谱可用于确定某些脂环族糖苷苷元部分的绝对构型，而无需用手性试剂合成衍生物。还研究了含有作为脂环族片段的糖基化侧链的海洋甾体糖苷及其乙酸酯的光谱。结果表明，在糖苷苷元部分的 D 环具有相同取代的情况下，通过 1H NMR 光谱分析来确定绝对构型更适用。
