lactulose | 802873-15-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: lactulose
• 英文别名: Duphalac；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S)-4,5-dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 802873-15-0
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: JCQLYHFGKNRPGE-DNMRROERSA-N

物化性质

• 沸点：
  680.5±55.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  lactulose 在 palladium dihydroxide 氢气 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 N-acetyl-D-lactosamine
  参考文献：
  名称：

  Heyns重排重新：从乳果糖的D-乳糖胺的异常简单的两步化学合成。

  摘要：

  通过标题反应，可以方便地由O-糖基化的D-果糖酶以高收率合成在还原端含有D-葡萄糖胺的二糖。（一种）]。在研究了所有二糖后，该方法得以继续进行，大概是因为O-4处的糖基残基与其他极性基团之间明显的去稳定作用-比未取代的D-果糖更有效，后者与氨反应生成D-葡萄糖胺Heyns和Koch在1950年代对它进行了描述。

  DOI：

  10.1002/(sici)1521-3773(19990315)38:6<827::aid-anie827>3.0.co;2-n
• 作为产物：
  描述：

  Lactose 在 deep sea water 作用下， 反应 0.08h， 以25.6%的产率得到lactulose
  参考文献：
  名称：

  One-pot isomerization of aldo-disaccharides to keto-disaccharides in deep sea water under sub-critical conditions

  摘要：

  A novel and facile one-pot isomerization of aldo-disaccharides to keto-disaccharides is achieved by making use of deep sea water in sub-critical conditions. The resulting keto-disaccharides having pharmaceutical and food applications were obtained in modest yields of about 30-32% at the optimum reaction conditions (temperature: 180 degrees C, reaction time: 5 min). Detailed investigation of all major ions in deep sea water revealed that bicarbonate ions play a key role as a catalyst in this isomerization reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.103

文献信息

• Subtilisin-catalyzed esterification of di- and oligosaccharides containing a d-fructose moiety
  作者：Sergio Riva、Micol Nonini、Gianluca Ottolina、Bruno Danieli

  DOI：10.1016/s0008-6215(98)00320-6

  日期：1998.12

  protease subtilisin in anhydrous dimethylformamide in the presence of the activated ester trifluoroethyl butanoate. Under the reaction conditions used, all the substrates were converted into the corresponding monobutanoates in ca. 50% isolated yields. Structural determination of the products by 13C NMR indicated a strong preference of subtilisin towards the regioselective esterification of the primary hydroxyls

  在活化的酯三氟乙基丁酸酯的存在下，在无水二甲基甲酰胺中，蛋白酶枯草杆菌蛋白酶将几种含有D-果糖部分的二糖和寡糖酰化。在所用的反应条件下，所有底物在约2℃下转化为相应的单丁酸酯。分离产率为50％。如通过蔗糖已经观察到的，通过13 C NMR对产物进行结构确定表明枯草杆菌蛋白酶对果糖部分的伯羟基，特别是C-1 OH的区域选择性酯化具有强烈的偏好。
• Production of keto-disaccharides from aldo-disaccharides in subcritical aqueous ethanol
  作者：Da-Ming Gao、Takashi Kobayashi、Shuji Adachi

  DOI：10.1080/09168451.2015.1127135

  日期：2016.5.3

  Isomerization of disaccharides (maltose, isomaltose, cellobiose, lactose, melibiose, palatinose, sucrose, and trehalose) was investigated in subcritical aqueous ethanol. A marked increase in the isomerization of aldo-disaccharides to keto-disaccharides was noted and their hydrolytic reactions were suppressed with increasing ethanol concentration. Under any study condition, the maximum yield of keto-disaccharides produced from aldo-disaccharides linked by β-glycosidic bond was higher than that produced from aldo-disaccharides linked by α-glycosidic bond. Palatinose, a keto-disaccharide, mainly underwent decomposition rather than isomerization in subcritical water and subcritical aqueous ethanol. No isomerization was noted for the non-reducing disaccharides trehalose and sucrose. The rate constant of maltose to maltulose isomerization almost doubled by changing solvent from subcritical water to 80 wt% aqueous ethanol at 220 °C. Increased maltose monohydrate concentration in feed decreased the conversion of maltose and the maximum yield of maltulose, but increased the productivity of maltulose. The maximum productivity of maltulose was ca. 41 g/(h kg-solution).

  摘要：在亚临界水乙醇中研究了二糖（麦芽糖、异麦芽糖、赤霉糖、乳糖、甜菜碱、蔗糖和海藻糖）的异构化反应。注意到醛基二糖向酮基二糖的异构化明显增加，随着乙醇浓度的增加，它们的水解反应被抑制。在任何研究条件下，通过β-糖苷键连接的醛基二糖产生的酮基二糖的最大产量均高于通过α-糖苷键连接的醛基二糖产生的酮基二糖。在亚临界水和亚临界水乙醇中，酮基二糖甘露糖主要发生分解而非异构化。非还原性二糖海藻糖和蔗糖未观察到异构化。将溶剂从亚临界水改为80%乙醇水溶液后，麦芽糖向麦芽糖酮异构化的速率常数几乎翻倍，温度为220°C。在进料中增加麦芽糖单水合物浓度会降低麦芽糖的转化率和麦芽糖的最大产量，但会提高麦芽糖的生产率。麦芽糖的最大生产率约为41克/（小时·千克-溶液）。
• An Exceptionally Simple Chemical Synthesis of<i>O</i>‐Glycosylated<scp>d</scp>‐Glucosamine Derivatives by Heyns Rearrangement of the Corresponding<i>O</i>‐Glycosyl Fructoses
  作者：Arnold E. Stütz、Gyula Dekany、Brigitte Eder、Carina Illaszewicz、Tanja M. Wrodnigg

  DOI：10.1081/car-120023468

  日期：2003.1.8

  2‐N‐Acetyl‐4‐O‐(β‐d‐galactopyranosyl)‐d‐glucosamine (N‐acetyl‐d‐lactosamine), a very important building block of biologically relevant oligosaccharides such as sialyl Lewisx, is easily accessible via the Heyns rearrangement of the corresponding O‐glycosylated ketohexose, d‐lactulose. This approach can also be extended to other glucosamine derivatives employing suitable O‐glycosylated ketoses many of

  2-N-乙酰基-4-O-（β-d-半乳糖吡喃糖基）-d-葡萄糖胺（N-乙酰基-d-乳糖胺）是生物学上重要的低聚糖的重要组成部分，例如唾液酸Lewisx，可通过相应的O-糖基化酮己糖，d-乳果糖的Heyns重排。这种方法还可以扩展到使用合适的O-糖基化酮糖的其他葡糖胺衍生物，其中许多是可商购的。例如，尼古拉明（3-O-α-d-吡喃葡萄糖基-d-果糖胺）是从杜兰糖（3-O-α-d-吡喃葡萄糖基-d-果糖）制备的。与最近引入的乙烯基酰胺类N-保护基团[1,3-二甲基-2-，4、6（1H，3H，5H）-三氧嘧啶-5-亚甲基]甲基（DTPM）结合使用时，这种访问方式显然更优越到其他路线，非常适合扩大规模。†本文专门针对Dr.
• Rapid Access to an Orthogonally Protected Lewis X Derivative: An Important Building Block for Synthesis of Lewis Antigens
  作者：Masashi Ohmae、Junko Takada、Hiroaki Murakami、Shunsaku Kimura

  DOI：10.1246/cl.2011.438

  日期：2011.5.5

  A novel Lewis X derivative of 1 with an orthogonal set of protecting groups was systematically prepared. Efficient use of the protecting groups for the amino and the hydroxy groups in lactosamine enabled formation of the diol derivative at C3 and C2′. Glycosidation of 1-thio-l-fucoside donor with the diol derivative progressed preferably at the C3 hydroxy group, resulting in prior production of 1. Compound 1 is a key building block toward easy assemblies of Lewis X-related carbohydrate epitopes.

  系统地制备了具有一组正交保护基团的新型路易斯X衍生物1。有效利用乳糖胺中氨基和羟基的保护基团能够在 C3 和 C2' 处形成二醇衍生物。 1-硫代-1-岩藻糖苷供体与二醇衍生物的糖苷化优选在 C3 羟基上进行，从而预先产生 1。化合物 1 是轻松组装 Lewis X 相关碳水化合物表位的关键构建模块。
• METHOD FOR PRODUCING OLIGOPOLYSACCHARIDES
  申请人：Samain Eric

  公开号：US20090082307A1

  公开（公告）日：2009-03-26

  The invention concerns the production by microbiological process of oligopolysaccharides of biological interest. More particularly, the invention concerns a method for synthesizing in vivo the oligopolysaccharides by internalization of an exogenous precursor in growing bacterial cells expressing adequate modifying and glycosylating genes.

  本发明涉及利用微生物过程生产生物学上感兴趣的寡聚多糖。更具体地，本发明涉及一种通过在表达适当的修饰和糖基化基因的生长细胞内摄取外源前体来体内合成寡聚多糖的方法。