3-O-α-D-glucopyranosyl-D-glucitol | 53776-84-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-O-α-D-glucopyranosyl-D-glucitol
• 英文别名: maltitol；Nigeritol；α-D-Glcp-(1->3)-D-Glc-ol；3-O-alpha-D-glucopyranosyl-D-glucitol；(2R,3R,4R,5S)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexane-1,2,3,5,6-pentol
• CAS: 53776-84-4
• 化学式: C₁₂H₂₄O₁₁
• 分子量: 344.316
• InChiKey: VQHSOMBJVWLPSR-NIKVEEOSSA-N

物化性质

• 沸点：
  788.5±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  201
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐-1,1-13C2 、 3-O-α-D-glucopyranosyl-D-glucitol 在 吡啶 作用下， 反应 24.0h， 生成
  参考文献：
  名称：

  具有13 C标记的羰基的全乙酰化寡糖的核磁共振波谱，而不是用于建立糖的键合取代的全甲基化分析。

  摘要：

  模型糖中的游离羟基被[13C-羰基]乙酸酐过乙酰化，导致NMR光谱中糖环质子信号的其他分裂，这是由于每个乙酰基羰基碳与糖环质子在该位置的3键J偶联。在不同的糖结构中对这些3键耦合常数中的144个进行定量显示，其范围在2.5至4.7 Hz之间，而糖环质子和乙酰羰基碳之间的所有可能的4键耦合均在线宽内（<0.5 Hz）。因此，在用[13C-羰基]乙酰基乙酰化后，在2.5-4.7Hz范围内糖环质子信号的进一步分裂将那个位置识别为（以前）具有游离羟基。它执行与全甲基化分析相同的基本功能，但不需要糖苷键的水解。另外，质子检测的2D异核多键相关（HMBC）实验或质子检测的异核相关光谱（hetCOSY）使环质子羰基13 C 3键J连通性具有较高的敏感性。据报道，已修改的NMR脉冲序列包括频率选择性解耦方案，可根据2D数据确定耦合常数。量身定制的脉冲序列可为[13C-羰基]环质子相关性带来更高的光谱分辨率

  DOI：

  10.1016/s0008-6215(98)00311-5
• 作为产物：
  描述：

  nigerose 在 sodium tetrahydroborate 作用下， 生成 3-O-α-D-glucopyranosyl-D-glucitol
  参考文献：
  名称：

  Co-ordinated synthesis of gentiobiitol and sorbitol, evidence of sorbitol glycosylation in transgenic sugarcane

  摘要：

  Sugarcane (a Saccharum spp. interspecific hybrid) was previously engineered to synthesize sorbitol (designated as sorbitolcane). Motivated by the atypical development of the leaves in some sorbitolcane, the polar metabolite profiles in the leaves of those plants were compared against a group of control sugarcane plants. Eighty-six polar metabolites were detected in leaf extracts by GC-MS. Principal component analysis of the metabolites indicated that three compounds were strongly associated with sorbitolcane. Two were identified as sorbitol and gentiobiose and the third was unknown. Gentiobiose and the unknown compound were positively correlated with sorbitol accumulation. The unknown compound was only abundant in sorbitolcane. This compound was structurally characterized and found to be a sorbitol-glucose conjugate. C-13 NMR analysis indicated that the glucopyranose and glucitol moieties were 1,6-linked. Ligand exchange chromatography confirmed that the compound was a beta-anomer, thus identifying the compound as 6-O-beta-D-glucopyranosyl-D-glucitol, or gentiobiitol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.01.014

文献信息

• Sequential Removal of Monosaccharides from the Reducing End of Oligosaccharides. 2. Fundamental Studies of a Reaction between Hydrazino Compounds and Sugars Having a Glycosyl Moiety on a Carbon Atom Adjacent to a Carbonyl Group
  作者：Brad Bendiak、Mary E. Salyan、Mario Pantoja

  DOI：10.1021/jo00130a026

  日期：1995.12

  Hydrazine and certain hydrazino derivatives react with sugars having a glycosidic substituent, where the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto group of the aglycon, resulting in cleavage of the glycosidic linkage. The reaction proceeds whether the glycon is of the alpha or beta configuration. The released glycosyl moiety, in the presence of excess hydrazino compound, reacts further to give a hydrazone derivative. Removal of the hydrazone group gives the reducing sugar derived from the glycon.
• SEQUENTIAL REMOVAL OF MONOSACCHARIDES FROM THE REDUCING END OF OLIGOSACCHARIDES AND USES THEREOF
  申请人：The Biomembrane Institute

  公开号：EP0649427A1

  公开（公告）日：1995-04-26
• US5403927A
  申请人：——

  公开号：US5403927A

  公开（公告）日：1995-04-04
• [EN] SEQUENTIAL REMOVAL OF MONOSACCHARIDES FROM THE REDUCING END OF OLIGOSACCHARIDES AND USES THEREOF<br/>[FR] PROCEDE D'ELIMINATION SEQUENTIELLE DE MONOSACCHARIDES DE L'EXTREMITE REDUCTRICE D'OLIGOSACCHARIDES ET UTILISATIONS DE CE PROCEDE
  申请人：THE BIOMEMBRANE INSTITUTE

  公开号：WO1993024503A1

  公开（公告）日：1993-12-09

  (EN) Methods are provided for the sequential removal of monosaccharides from the reducing end of oligosaccharides. The present invention also discloses the use of such methods for structural determinations of oligosaccharides and to enable new structures to be generated from pre-existing oligosaccharides. In addition, the methods of the present invention may be automated by the incorporation into systems.(FR) Des procédés destinés à l'élimination séquentielle de monosaccharides de l'extrémité réductrice d'oligosaccharides sont décrits. La présente invention se rapporte également à l'utilisation de tels procédés pour déterminer les structures des oligosaccharides et pour permettre à de nouvelles structures d'être générées à partir d'oligosaccharides existants déjà. En outre, les procédés de la présente invention peuvent être automatisés par incorporation dans des systèmes.
• WO2005/14608
  申请人：——

  公开号：——

  公开（公告）日：——