(S)-(+)-iopanoic acid | 17879-96-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-(+)-iopanoic acid
• 英文别名: Benzenepropanoic acid, 3-amino-alpha-ethyl-2,4,6-triiodo-, (alphaS)-；(2S)-2-[(3-amino-2,4,6-triiodophenyl)methyl]butanoic acid
• CAS: 17879-96-8
• 化学式: C₁₁H₁₂I₃NO₂
• 分子量: 570.935
• InChiKey: OIRFJRBSRORBCM-YFKPBYRVSA-N

物化性质

• 熔点：
  162°
• 比旋光度：
  D20 +5.1 ± 0.1° (c = 2 in ethanol)
• 沸点：
  529.1±50.0 °C(Predicted)
• 密度：
  2.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-iopanoic acid 在 4-二甲氨基吡啶 、 硼酸 、 silica gel 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 、 Petroleum ether 为溶剂， 生成 1-palmitoyl-2(S)-iopanoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and evaluation of iodinated analogs of diacylglycerols as potential probes for protein kinase C

  摘要：

  Analogues of diacylglycerol containing a 3-(3-amino-2,4,6-triiodophenyl)-2-ethylpropanoyl or 3-(3-amino-2,4,6-triiodophenyl)propanoyl group in the 2-position (1a and 1b, respectively) were synthesized and shown to compete with [3H]phorbol dibutyrate [( 3H]PDBu) for binding in a crude rat brain preparation. Phorbol diesters have been shown to bind specifically to protein kinase C and the PDBu receptor has been copurified with protein kinase C activity. The four diastereomers of 1a (1c-f) were synthesized from chiral starting material and studied in the same assay. The affinities for the [3H]PDBu binding site of 1a, 1b, and two isomers of 1a with naturally occurring L configuration were comparable to that of 1-oleoyl-2-acetyl-rac-glycerol (OAG), but the D isomers of 1a were essentially inactive. The chirality of the side chain did not influence the binding affinity. Activation of protein kinase C by 1a, 1c, and 1e demonstrated the same stereochemical requirements, but none were as active as OAG. For the 1,3-isomers 2, 2a, and 2b, the competitive binding studies gave different results. The racemic mixture and the D isomer, 2b, were able to compete for binding, but the L isomer, 2a, did not compete. These studies demonstrate that diacylglycerol binding to and activation of protein kinase C is stereospecific for the glycerol backbone, but not the side chain. Furthermore, the D-1,3-isomer must exist in a conformation such that the acyl and hydroxyl oxygens assume a spatial relationship similar to that in the L-1,2-isomers.

  DOI：

  10.1021/jm00123a024
• 作为产物：
  描述：

  碘番酸 以21%的产率得到
  参考文献：
  名称：

  STRAWN, LAURIE M.;MARTELL, ROBERT E.;SIMPSON, ROBERT U.;LEACH, KAREN L.;C+, J. MED. CHEM., 32,(1989) N, C. 643-648

  摘要：

  DOI：

文献信息

• Chemoenzymatic synthesis of the enantiomers of iopanoic acid
  作者：M. Colombo、M. De Amici、C. De Micheli、D. Pitré、G. Carrea、S. Riva

  DOI：10.1016/s0957-4166(00)86152-2

  日期：1991.1

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.