rhamnolipid | 125135-03-7

• 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: rhamnolipid
• 英文别名: (r)-3-((r)-3-((2r,3r,4r,5r,6s)-4,5-Dihydroxy-6-methyl-3-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)tetrahydro-2h-pyran-2-yloxy)decanoyloxy)decanoic acid；(3R)-3-[(3R)-3-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxydecanoyl]oxydecanoic acid
• CAS: 125135-03-7
• 化学式: C₃₂H₅₈O₁₃
• 分子量: 650.805
• InChiKey: FCBUKWWQSZQDDI-HYFZAEJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  45
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 rhamnolipid 以 四氢呋喃 为溶剂， 生成 methyl (3R)-3-[(3R)-3-(2-O-α-L-rhamnopyranosyl-α-L-rhamnopyranosyloxy)decanoyloxy]decanoate
  参考文献：
  名称：

  (R)-3-{(R)-3-[2-O-(α-L-Rhamnopyranosyl)-α-L-rhamnopyranosyl] oxydecanoyl}oxydecanoic Acid 的有效合成，一种来自铜绿假单胞菌的鼠李糖脂

  摘要：

  N-碘代琥珀酰亚胺/三氟甲磺酸介导的 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside (8) 与苯基 3,4-O-(2) 的一锅两步糖基化,3-二甲氧基丁烷-2,3-二基)-1-硫代-α-L-吡喃鼠李糖苷(10b)和苯甲酰(R)-3-羟基癸酸酯(13)得到鼠李糖脂17。后者分五步转化为标题化合物2。2与重氮甲烷的酯化产生相应的甲酯衍生物1。

  DOI：

  10.1002/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u
• 作为产物：
  描述：

  果糖 在 pseudomonas-aeruginosa-cultures 作用下， 生成 rhamnolipid
  参考文献：
  名称：

  Hauser; Karnovsky, Journal of Bacteriology, 1954, vol. 68, p. 645,651

  摘要：

  DOI：
• 作为试剂：
  描述：

  水 、 calcium chloride 、 硫酸氢铵 在 rhamnolipid 作用下， 反应 1.17h， 生成 calcium sulfate dihydrate
  参考文献：
  名称：

  Ultrasound-assisted/biosurfactant-templated size-tunable synthesis of nano-calcium sulfate with controllable crystal morphology

  摘要：

  Nano-sized crystals of alpha calcium sulfate hemihydrate (cc-HH) with considerable morphology-dependent properties find promising applications in the clinical fields as a cementitious material. Towards this end, ultrasound-assisted rhamnolipid and surfactin biosurfactant-template route is explored to control the morphology and aspect ratio of nano-CaSO4 by adjusting the mass ratio of rhamnolipid/H2O, surfactin/H2O and rhamnolipid/surfactin. The change in the molar ratio of [SO42-]:[Ca2+] results in modification in variable morphology and size of nano-CaSO4 including long, short rods and nanoplates. With increase in the rhamnolipid/H2O ratio from 1.3 to 4.5, the crystal length decreases from 3 um to 600 nm with the corresponding aspect ratio reduced sharply from 10 to 3. Similarly, the crystal morphology gradually changes from submicrometer-sized long rod to hexagonal plate, and then plate-like appearance with increase in surfactin concentration. The preferential adsorption of rhamnolipid on the side facets and surfactin on the top facets contributes to the morphology control. The process using 50% amplitude with a power input of 45.5 W was found to be the most ideal as observed from the high yields and lower average l/w aspect ratio, leading to more than 94% energy savings as compared to that utilized by the conventional process. As a morphology and crystal habit modifier, effects of Mg2+ and K+ ions on alpha-HH growth were investigated to find an optimal composition of solution for alpha-HH preparation. Mg2+ ions apparently show an accelerating effect on the alpha-HH growth; however, the nucleation of alpha-HH is probably retarded by K* ions. Thus, the present work is a simple, versatile, highly efficient approach to controlling the morphology of alpha-HH and thereby, offers more opportunities for ot-HH multiple applications. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2013.12.020

文献信息

• Synthesis of α-1,2- and α-1,3-linked di-rhamnolipids for biological studies
  作者：Fruzsina Demeter、Margaret Dah-Tsyr Chang、Yuan-Chuan Lee、Tse-Kai Fu、Mihály Herczeg、Anikó Borbás

  DOI：10.1016/j.carres.2020.108102

  日期：2020.10

  di-lipid derivatives, transformation of which into the target compounds was accomplished in two steps. This method allows the synthesis of both regioisomers in only 6 steps starting from the corresponding free disaccharides. Both synthetic di-rhamnolipids were biologically active for lectin binding differential binding preference between two isomeric di-rhamno-di-lipids. The rHPL lectin favours the

  为了详细检查含鼠李糖的衍生物与重组马蹄蟹血浆凝集素（rHPL）的相互作用，通过以下方法合成了两个二鼠李二脂（α-1,2-和α-1,3-连接）一种新的简单方法。（R）-3-羟基癸酸甲酯与苯基-1-硫代鼠李糖双糖苷供体的N-碘代琥珀酰亚胺/三氟甲磺酸介导的糖基化作用提供了单脂质二糖。除去甲酯基团，然后用第二个（R）-3-羟基癸酸酯单元将单脂质酯化，得到完全保护的双脂质衍生物，将其转化为目标化合物可分两步完成。该方法允许从相应的游离二糖开始仅6个步骤合成两种区域异构体。两种合成的二鼠李糖脂对于凝集素结合具有生物学活性，这两种异构体二鼠李糖二脂之间的结合偏好不同。rHPL凝集素比其α-1,2连接的区域异构体更倾向于α-1,3-连接的双鼠李二脂。
• Konzentrierte, niedrigviskose Rhamnolipid-Zusammensetzungen
  申请人：Evonik Degussa GmbH

  公开号：EP3023431A1

  公开（公告）日：2016-05-25

  Gegenstand der Erfindung sind konzentrierte Rhamnolipid-Zusammensetzungen sowie Verfahren zu ihrer Herstellung.

  本发明涉及浓缩鼠李糖脂组合物及其制备工艺。
• Concentrated, low-viscosity rhamnolipid compositions
  申请人：Evonik Degussa GmbH

  公开号：US10604722B2

  公开（公告）日：2020-03-31

  A rhamnolipid composition including 30% by weight to 70% by weight, of at least one rhamnolipid and 30% by weight to 70% by weight of water, where the percentages by weight refer to the total composition, wherein the pH of the composition at 25° C. is from 5.5 to 7.0. In addition to the foregoing rhamnolipid composition, also set forth is a method to make a solution of rhamnolipids; and salt of at least one rhamnolipid.

  一种鼠李糖脂组合物，包括 30%（重量）至 70%（重量）的至少一种鼠李糖脂和 30%（重量）至 70%（重量）的水，其中重量百分比是指总组合物，其中组合物在 25°C 时的 pH 值为 5.5 至 7.0。除上述鼠李糖脂组合物外，还提出了一种制取鼠李糖脂溶液的方法；以及至少一种鼠李糖脂的盐。
• Edwards; Hayashi, Archives of Biochemistry, <hi>1965</hi>, vol. 111, p. 415,421
  作者：Edwards、Hayashi

  DOI：——

  日期：——
• A Glyco-lipide Produced by <i>Pseudomonas Aeruginosa</i>
  作者：F. G. Jarvis、M. J. Johnson

  DOI：10.1021/ja01180a073

  日期：1949.12