4-O-β-L-吡喃半乳糖基-β-D-吡喃葡萄糖苷甲酯（β-L-乳糖甲酯）
Methyl 4-O-beta-L-galactopyranosyl-beta-D-glucopyranoside (methyl beta-L-lactoside).
作者信息
Pan Qingfeng, Noll Bruce C, Serianni Anthony S
机构信息
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, IN 46556, USA.
出版信息
Acta Crystallogr C. 2006 Feb;62(Pt 2):o82-5. doi: 10.1107/S010827010504254X. Epub 2006 Jan 21.
Methyl beta-L-lactoside, C13H24O11, (II), is described by glycosidic torsion angles phi (O5Gal-C1Gal-O4Glc-C4Glc) and psi (C1Gal-O1Gal-C4Glc-C5Glc) of 93.89 (13) and -127.43 (13) degrees , respectively, where the ring atom numbering conforms to the convention in which C1 is the anomeric C atom and C6 is the exocyclic hydroxymethyl (CH2OH) C atom in both residues (Gal is galactose and Glc is glucose). Substitution of L-Gal for D-Gal in the biologically relevant disaccharide, methyl beta-lactoside [Stenutz, Shang & Serianni (1999). Acta Cryst. C55, 1719-1721], (I), significantly alters the glycosidic linkage interface. In the crystal structure of (I), one inter-residue (intramolecular) hydrogen bond is observed between atoms H3OGlc and O5Gal. In contrast, in the crystal structure of (II), inter-residue hydrogen bonds are observed between atoms H6OGlc and O5Gal, H6OGlc and O6Gal, and H3OGlc and O2Gal, with H6OGlc serving as a donor with two intramolecular acceptors.
β-L-乳糖苷，化学式为C13H24O11，（II），其糖苷扭转角φ（O5Gal-C1Gal-O4Glc-C4Glc）和ψ（C1Gal-O1Gal-C4Glc-C5Glc）分别为93.89（13）度和-127.43（13）度，其中环原子编号符合如下惯例：在两个残基中，C1均为异头C原子，C6均为环外羟甲基（CH2OH）C原子（Gal为半乳糖，Glc为葡萄糖）。在具有生物学相关性的二糖β-乳糖苷[Stenutz、Shang和Serianni（1999年）。《晶体学报》C55卷，1719 - 1721页]，（I）中，用L-Gal取代D-Gal会显著改变糖苷键连接界面。在（I）的晶体结构中，观察到在H3OGlc和O5Gal原子之间存在一个残基间（分子内）氢键。相比之下，在（II）的晶体结构中，观察到在H6OGlc和O5Gal、H6OGlc和O6Gal以及H3OGlc和O2Gal原子之间存在残基间氢键，其中H6OGlc作为一个供体与两个分子内受体形成氢键。
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