(S)-3-hydroxyoctanoic acid benzyl ester | 126442-53-3

• 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: (S)-3-hydroxyoctanoic acid benzyl ester
• 英文别名: benzyl (3R)-3-hydroxyoctanoate；(R)-benzyl 3-hydroxyoctanoate；benzyl 3-hydroxyoctanoate；Benzyl 3-hydroxyoctanate
• CAS: 126442-53-3
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: UNJZFNRAJJMUMM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (S)-3-hydroxyoctanoic acid benzyl ester 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 84.24h， 生成 (10S,13S,16S,19S)-(R)-1-(benzyloxy)-1-oxooctan-3-yl 10-((tert-butoxycarbonyl)amino)-13,16,19-triisobutyl-2,2-dimethyl-4,11,14,17-tetraoxo-3-oxa-5,12,15,18-tetraazaicosan-20-oate
  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：

  (R)-3-羟基辛酸甲酯 在 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-3-hydroxyoctanoic acid benzyl ester
  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

• Total synthesis and structural validation of cyclodepsipeptides solonamide A and B
  作者：Betül Kitir、Mara Baldry、Hanne Ingmer、Christian A. Olsen

  DOI：10.1016/j.tet.2014.05.107

  日期：2014.10

  I (AIP-I). To enable more comprehensive studies, we embarked on the chemical synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereo-selective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures

  微生物是具有抗菌特性的新天然产物的诱人来源，海洋环境构成了生物活性微生物的丰富资源。在一项全球研究探险活动（Galathea III）中，从海洋细菌光致细菌耐盐细菌中分离出了两种depsipeptide，即solonamide A和solonamide B，并发现它们可抑制严重人类病原体金黄色葡萄球菌中的毒力基因表达。它们通过干扰农业群体感应系统来发挥作用，并显示出与内源性金黄色葡萄球菌的相似之处。群体感应肽，自动诱导肽I（AIP-1）。为了进行更全面的研究，我们着手化学合成了磺酰胺A和B。关键的合成步骤是通过立体选择性羟醛反应和环化大内酰胺化反应形成（R）-β-羟基脂肪酸。在高度稀薄的条件下。因此，solonamides的第一个全合成证实了最初分配的结构，并通过改变辅助的立体醛醇缩合步骤中，我们获得了对天然产品接入以及他们β 3差向异构体。
• Asymmetric aldol-type reaction between both achiral ketene silyl acetals of acetic acid esters and aldehydes by the use of a chiral promoter
  作者：Teruaki Mukaiyama、Shū Kobayashi、Tetsuya Sano

  DOI：10.1016/s0040-4020(01)85587-3

  日期：——

  aldol-type reaction between achiral ketene silyl acetals of acetic acid esters and achiral aldehydes is successfully carried out by the use of a chiral promoter, a combined use of chiral diamine coordinated tin(II) trifluoromethanesulfonate (tin(II) triflate) and tributyltin fluoride. The structure of this new promoter and the mechanism of the present asymmetric aldol-type reaction are discussed.

  通过使用手性促进剂，手性二胺配位的三氟甲磺酸锡（II）（三氟甲磺酸锡（II））和三丁基氟化锡。讨论了该新启动子的结构和当前不对称醛醇型反应的机理。
• Tuning StackPhim Ligands: Applications in Enantioselective Borylation and Alkynylation
  作者：Aaron Aponick、Gaurav Dahiya、Khalil A. Abboud

  DOI：10.1055/a-1730-2473

  日期：2022.5

  Here we present a new stack ligand with a modified imidazoline backbone prepared from cyclohexanediamine. This new stack ligand­, Cy-StackPhim, has been found to complement the parent StackPhim ligand in an enantioselective borylation reaction. Additionally, a correlation between the nature of substituents on the imidazoline ring and the substituents on the electrophile is also discussed.

  在这里，我们介绍了一种新的堆叠配体，它是由环己二胺制备的改性咪唑啉骨架。这种新的堆叠配体Cy-StackPhim已被发现在对映选择性硼化反应中与母体StackPhim配体相互补充。此外，还讨论了咪唑啉环上取代基的性质与电荷亲和性取代基的性质之间的相关性。

• Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds
  作者：Jelena Radivojevic、Sanja Skaro、Lidija Senerovic、Branka Vasiljevic、Maciej Guzik、Shane T. Kenny、Veselin Maslak、Jasmina Nikodinovic-Runic、Kevin E. O’Connor

  DOI：10.1007/s00253-015-6984-4

  日期：2016.1

  A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.