2-O-(4-deoxy-β-L-threo-hex-4-enopyranuronosyl)-L-rhamnopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(4-deoxy-β-L-threo-hex-4-enopyranuronosyl)-L-rhamnopyranose
• 英文别名: β-L-δ^4,5HexpA-(1->2)-L-Rha；lepidimoic acid；(2S,3R,4S)-3,4-dihydroxy-2-[(3R,4R,5R,6S)-2,4,5-trihydroxy-6-methyloxan-3-yl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• 化学式: C₁₂H₁₈O₁₀
• 分子量: 322.269
• InChiKey: PBUKNNGDHZLXKG-BMGZRBPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-O-(4-deoxy-β-L-threo-hex-4-enopyranuronosyl)-L-rhamnopyranose 在 N-溴代丁二酰亚胺(NBS) 、 ammonium formate 作用下， 生成 L-rhamnopyranose
  参考文献：
  名称：

  鼠李糖半乳糖醛酸的选择性化学裂解的改进程序。

  摘要：

  支链鼠李半乳糖醛酸聚糖（RGs）的结构表征需要有选择性裂解Rhap-（1-> 4）-α-GalAp键从而生成适用于质谱和NMR光谱分析的寡糖片段的方法。这种连接的酶切作用通常是无效的，特别是在高度分支的RGs中。因此，我们已经开发出一种基于β消除酯化的4连接的GalpA残基的改进的化学裂解方法。使用甲基碘或3-碘丙醇在含有8％水和1％四丁基氟化铵的Me（2）SO中酯化拟南芥种子黏液RG中GalA残基的至少85％的羧基。但是，在pH 7时β消除片段化。羟丙基酯化的RG在3和120摄氏度下的扩散比甲基酯化的RG更为广泛。通过用N-溴代琥珀酰亚胺水溶液处理，完全消除了由β-消除反应形成的非还原性4-脱氧-β-1-苏-hex-4-烯基吡喃糖基糖醛酸残基，从而简化了化学生成的寡糖基片段的结构表征。该新开发的程序用于选择性地使胡椒草种子粘液中的支链RG片段化。使用MALDI-TOF质谱，糖基残基组成分析以及1D和2D

  DOI：

  10.1016/j.carres.2008.11.011
• 作为产物：
  描述：

  sodium methylate 、 (2S,3R,4S,5R,6S)-3,4,5-Trihydroxy-6-((3R,4R,5R,6S)-2,4,5-trihydroxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 2-O-(4-deoxy-β-L-threo-hex-4-enopyranuronosyl)-L-rhamnopyranose 、 2-O-(4-deoxy-β-L-threo-hex-4-enopyranuronosyl)-β-L-rhamnopyranose methylglycoside
  参考文献：
  名称：

  Preparation of a growth-promoting substance, lepidimoic acid, from okra pectic polysaccharide

  摘要：

  Lepidimoic acid, a 1,2-cis-linked disaccharide, is an interesting plant growth-promoting substance and has been synthesized from D-glucose and L-rhamnose by Kosemura et al., 1993. Fry et al., 1993, in view of the biosynthetic origin, suggested that it could be produced by the cleavage of a pectic polysaccharide such as rhamnogalacturonan. In this study lepidimoic acid was prepared from okra (Hibiscus esculentus L.) pectic polysaccharide in a passable yield by sequential decomposition reactions. The plant growth-promoting activity of the prepared lepidimoic acid was confirmed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00153-9

文献信息

• Preparation of a growth-promoting substance, lepidimoic acid, from okra pectic polysaccharide
  作者：Katsutoshi Hirose、Yasutaka Kosuge、Toshihiko Otomatsu、Keiichiro Endo、Koji Hasegawa

  DOI：10.1016/s0040-4039(03)00153-9

  日期：2003.3

  Lepidimoic acid, a 1,2-cis-linked disaccharide, is an interesting plant growth-promoting substance and has been synthesized from D-glucose and L-rhamnose by Kosemura et al., 1993. Fry et al., 1993, in view of the biosynthetic origin, suggested that it could be produced by the cleavage of a pectic polysaccharide such as rhamnogalacturonan. In this study lepidimoic acid was prepared from okra (Hibiscus esculentus L.) pectic polysaccharide in a passable yield by sequential decomposition reactions. The plant growth-promoting activity of the prepared lepidimoic acid was confirmed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Improved procedures for the selective chemical fragmentation of rhamnogalacturonans
  作者：Chenghua Deng、Malcolm A. O’Neill、Michael G. Hahn、William S. York

  DOI：10.1016/j.carres.2008.11.011

  日期：2009.9

  containing 8% water and 1% tetrabutylammonium fluoride. However, beta-elimination fragmentation at pH 7.3 and 120 degrees C is far more extensive with hydroxypropyl-esterified RG than with methyl-esterified RG. The non-reducing 4-deoxy-beta-l-threo-hex-4-enepyranosyluronic acid residue formed by the beta-elimination reaction is completely removed by treatment with aqueous N-bromosuccinimide, thereby simplifying

  支链鼠李半乳糖醛酸聚糖（RGs）的结构表征需要有选择性裂解Rhap-（1-> 4）-α-GalAp键从而生成适用于质谱和NMR光谱分析的寡糖片段的方法。这种连接的酶切作用通常是无效的，特别是在高度分支的RGs中。因此，我们已经开发出一种基于β消除酯化的4连接的GalpA残基的改进的化学裂解方法。使用甲基碘或3-碘丙醇在含有8％水和1％四丁基氟化铵的Me（2）SO中酯化拟南芥种子黏液RG中GalA残基的至少85％的羧基。但是，在pH 7时β消除片段化。羟丙基酯化的RG在3和120摄氏度下的扩散比甲基酯化的RG更为广泛。通过用N-溴代琥珀酰亚胺水溶液处理，完全消除了由β-消除反应形成的非还原性4-脱氧-β-1-苏-hex-4-烯基吡喃糖基糖醛酸残基，从而简化了化学生成的寡糖基片段的结构表征。该新开发的程序用于选择性地使胡椒草种子粘液中的支链RG片段化。使用MALDI-TOF质谱，糖基残基组成分析以及1D和2D