DL-β-Hydroxydodecansaeurebenzylester | 53941-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: DL-β-Hydroxydodecansaeurebenzylester
• 英文别名: benzyl 3-hydroxydodecanoate
• CAS: 53941-37-0
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: XGVQLQWPVWIELS-UHFFFAOYSA-N

物化性质

• 沸点：
  432.3±20.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  22.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  DL-β-Hydroxydodecansaeurebenzylester 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 benzyl 3-(((S)-2-amino-4-methylpentanoyl)oxy)dodecanoate
  参考文献：
  名称：

  Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

  摘要：

  Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties.Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

  DOI：

  10.1016/j.bioorg.2019.03.023
• 作为产物：
  描述：

  癸醛 在 potassium carbonate 、 lithium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 27.0h， 生成 DL-β-Hydroxydodecansaeurebenzylester
  参考文献：
  名称：

  Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

  摘要：

  Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties.Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

  DOI：

  10.1016/j.bioorg.2019.03.023

文献信息

• Solid phase synthesis of isariin, a long chain .BETA.-hydroxy acid-containing cyclodepsipeptide, and its diastereoisomer.
  作者：KOZO OKADA、YOTARO KUROSAWA、MINORU HIRAMOTO

  DOI：10.1248/cpb.22.2136

  日期：——

  The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC-Val-DL-Hyd-OH, alanine, and Z-Val-D-Leu-OH to resin-bound glycine using dicyclohexylcarbodiimide (DCC) or DCC+hydroxysuccinimide (HOSu) as coupling agent. After cleavage from the resin the depsipeptide was cyclized by means of DCC+HOSu. The cyclization product was successfully resolved, after chromatographic purification on Dowex 50×4 and Sephadex LH-20 column, by preparative thin-layer chromatography on silica gel to afford Ia and Ib in moderate yields.

  应用固相合成法制备了一种含β-羟基十二烷酸的白花蛇舌草环十二肽代谢物--白花蛇舌草素（Ia）及其异构体（Ib）。以二环己基碳二亚胺（DCC）或 DCC+ 羟基琥珀酰亚胺（HOSu）为偶联剂，通过将 BOC-Val-DL-Hyd-OH、丙氨酸和 Z-Val-D-Leu-OH 相继与树脂结合的甘氨酸偶联，合成了开链去肽 H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH。从树脂裂解后，去肽通过 DCC+HOSu 环化。环化产物在 Dowex 50×4 和 Sephadex LH-20 色谱柱上色谱纯化后，通过硅胶制备型薄层色谱法成功分离，得到 Ia 和 Ib，收率适中。