methyl (11R,12S)-lactobacillate | 112418-57-2

• 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: methyl (11R,12S)-lactobacillate
• 英文别名: methyl (Z)-10-(2-hexylcyclopropan-1-yl)decanoate；methyl lactobacillate；10-((1R)-cis-2-hexyl-cyclopropyl)-decanoic acid methyl ester；10-((1R)-cis-2-Hexyl-cyclopropyl)-decansaeure-methylester；methyl 10-[(1R,2S)-2-hexylcyclopropyl]decanoate
• CAS: 112418-57-2
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: HASAQWANQLNRRS-RBUKOAKNSA-N

物化性质

• 沸点：
  362.7±10.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (11R,12S)-lactobacillate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以55%的产率得到10-(2-己基环丙基)癸酸
  参考文献：
  名称：

  The synthesis of (11R,12S)-lactobacillic acid and its enantiomer

  摘要：

  (LS,12S)-乳酸杆菌酸已从2,3-O异丙烯基-D-甘油醛中制备，其中涉及非对映异构物环丙烷化，以及从顺式环丙烷-1,2-二甲醇中使用酶催化去对称化。前一条路线的关键步骤是通过对(1Z,4S')-(2',2'-二甲基-1',3'-二氧杂环戊烷-4'-基)-1-辛烯进行Simmons-Smith型反应进行立体化学控制的环丙烷化，使用了二乙基锌和碘氯甲烷。该产品被转化为关键中间体(1R,2S)-1-甲酰基-2-己基环丙烷，该中间体也可通过已知路线从顺式环丙烷-1,2-二甲醇的(1R,2S)-单丁酸酯获得。这种关键的醛被转化为(11R,12S)-乳酸杆菌酸。通过类似化学，乳酸杆菌酸的(11S,12R)-对映异构体从2,3-O异丙烯基-D-甘油醛或顺式环丙烷-1,2-二甲醇的(1S,R)-单丁酸酯中制备。 (C) 2003 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0957-4166(03)00165-4
• 作为产物：
  描述：

  10-(2-己基环丙基)癸酸 生成 methyl (11R,12S)-lactobacillate
  参考文献：
  名称：

  二烷基-1,2-顺式环丙烷绝对构型的测定：乳酸菌绝对构型的测定

  摘要：

  描述了一种测定顺式-1，2-二烷基环丙烷的绝对构型的方法。该方法基于将这些化合物温和地铬氧化为与相同种类和已知构型的酮有关的α-环丙基酮。将该方法应用于乳核酸，得到的是11R，12S-亚甲基-十八烷二酸。

  DOI：

  10.1016/0040-4020(72)80144-3

文献信息

• Bioactive lipids from the sponge Spirastrella abata
  作者：Kyoung Hwa Jang、Yoonyeong Lee、Chung J. Sim、Ki-Bong Oh、Jongheon Shin

  DOI：10.1016/j.bmcl.2011.11.105

  日期：2012.1

  Three sphingosine 4-sulfates (1-3) and a lysophosphatidylglycerol (4) were isolated from the Korean sponge Spirastrella abata. The structures of these compounds were determined based on the combined results of spectroscopic analyses. Based on the results of combined synthesis and comparison of specific rotation and circular dichroism, the absolute configurations of 1-3 were found to be enantiomeric to the previously isolated metabolites. The configurations of 4 were also partially determined by similar chemical and spectroscopic methods. The compounds exhibited significant cytotoxicity and weak antimicrobial activity (1), as well as weak-to-moderate inhibitory activity against isocitrate lyase and Na+/K+-ATPase. A structure-activity relationship was found for the sphingosine 4-sulfates. (C) 2011 Elsevier Ltd. All rights reserved.
• Configurational Analysis of Cyclopropyl Fatty Acids Isolated from <i>Escherichia coli</i>
  作者：Laura J. Stuart、James P. Buck、Amy E. Tremblay、Peter H. Buist

  DOI：10.1021/ol052550d

  日期：2006.1.1

  The absolute configuration of methyl lactobacillate and its 9,10 homologue, both isolated from Escherichia coli B-ATCC 11303, was found to be 11R,12S and 9R,10S, respectively.
• HOFMANN; TAUSIG, Journal of Biological Chemistry, 1955, vol. 213, # 1, p. 425 - 432
  作者：HOFMANN、TAUSIG

  DOI：——

  日期：——
• Hofmann et al., Journal of Biological Chemistry, 1952, vol. 195, p. 473,479
  作者：Hofmann et al.

  DOI：——

  日期：——
• The synthesis of (11R,12S)-lactobacillic acid and its enantiomer
  作者：Geoffrey D. Coxon、Juma R. Al-Dulayymi、Mark S. Baird、Stefan Knobl、Evan Roberts、David E. Minnikin

  DOI：10.1016/s0957-4166(03)00165-4

  日期：2003.5

  (11R,12S)-Lactobacillic acid has been prepared from 2,3-O-isopropylidene-D-glyceraldehyde, in a sequence involving asymmetric cyclopropanation, and from cis-cyclopropane-1,2-dimethanol, using enzymatic desymmetrisation. The key step in the former route was the stereochemically controlled cyclopropanation of (1Z,4'S)-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-octene via a Simmons-Smith type reaction, using diethylzinc and chloroiodomethane. This product was converted into the key intermediate (1R,2S)-1-formyl-2-hexylcyclopropane, which was also obtained by a known sequence from the (1R,2S)-monobutyrate ester of cis-cyclopropane-1,2-dimethanol. This pivotal aldehyde was converted into (11R,12S)-lactobacillic acid. Using analogous chemistry, the (11S,12R)-enantiomer of lactobacillic acid was prepared from 2,3-O-isopropylidene-D-glyceraldehyde or from the (1S,R)-monobutyrate ester of cis-cyclopropane-1,2-dimethanol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  (LS,12S)-乳酸杆菌酸已从2,3-O异丙烯基-D-甘油醛中制备，其中涉及非对映异构物环丙烷化，以及从顺式环丙烷-1,2-二甲醇中使用酶催化去对称化。前一条路线的关键步骤是通过对(1Z,4S')-(2',2'-二甲基-1',3'-二氧杂环戊烷-4'-基)-1-辛烯进行Simmons-Smith型反应进行立体化学控制的环丙烷化，使用了二乙基锌和碘氯甲烷。该产品被转化为关键中间体(1R,2S)-1-甲酰基-2-己基环丙烷，该中间体也可通过已知路线从顺式环丙烷-1,2-二甲醇的(1R,2S)-单丁酸酯获得。这种关键的醛被转化为(11R,12S)-乳酸杆菌酸。通过类似化学，乳酸杆菌酸的(11S,12R)-对映异构体从2,3-O异丙烯基-D-甘油醛或顺式环丙烷-1,2-二甲醇的(1S,R)-单丁酸酯中制备。 (C) 2003 Elsevier Science Ltd. 保留所有权利。