sophoritol | 31281-78-4

• 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: sophoritol
• 英文别名: (2R,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexane-1,2,3,4,6-pentol
• CAS: 31281-78-4
• 化学式: C₁₂H₂₄O₁₁
• 分子量: 344.316
• InChiKey: LSRAJKPAPWYOQO-VNNZMYODSA-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

• 作为产物：
  描述：

  2-O-beta-D-吡喃葡萄糖基-alpha-D-吡喃葡萄糖 在 sodium tetrahydroborate 作用下， 生成 sophoritol
  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

• US4024290A
  申请人：——

  公开号：US4024290A

  公开（公告）日：1977-05-17
• Co-ordinated synthesis of gentiobiitol and sorbitol, evidence of sorbitol glycosylation in transgenic sugarcane
  作者：Barrie Fong Chong、W.P.P. Abeydeera、Donna Glassop、Graham D. Bonnett、Michael G. O’Shea、Stevens M. Brumbley

  DOI：10.1016/j.phytochem.2010.01.014

  日期：2010.5

  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.