Z-Ala-Pro^P(OPh)2 | 341552-38-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Z-Ala-Pro^P(OPh)2
• 英文别名: Diphenyl 1-(N-Cbz-(S)-alanyl) pyrrolidine-2-phosphonate；benzyl N-[(2S)-1-(2-diphenoxyphosphorylpyrrolidin-1-yl)-1-oxopropan-2-yl]carbamate
• CAS: 341552-38-3
• 化学式: C₂₇H₂₉N₂O₆P
• 分子量: 508.511
• InChiKey: WJOMUWWHSLOYLV-BWDMCYIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-Ala-Pro^P(OPh)2 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以65%的产率得到diphenyl alanylpyrrolidine-2-phosphonate hydrobromide
  参考文献：
  名称：

  Dipeptide Phosphonates as Inhibitors of Dipeptidyl Peptidase IV

  摘要：

  A series of dipeptides which contained phosphonate analogs of proline and piperidine-2-carboxylic acid (homoproline) have been synthesized and tested as inhibitors of DPP-IV. The rates of inhibition of DPP-IV by these compounds are moderate, but the inhibitors are quite specific. The best inhibitor in the series is Ala-Pip(P)(OPh-4-Cl)(2) (13), which has a k(inact) of 0.353 s(-1) and K-I of 236 mu M. The DPP-IV inhibitors Ala-Pro(P)(OPh)(2) (6), Ala-Pro(P)(OPh-4-Cl)(2) (12), and Ala-Pip(P)(OPh-4-Cl)(2) (13) do not inhibit trypsin, human leukocyte elastase (HLE), porcine pancreatic elastase (PPE), adetylcholinesterase, papain, and cathepsin B. However, compounds 12 and 13 inhibited chymotrypsin slowly. Most of these dipeptides containing a homoproline phosphonate residue (Pip(P)) or a Pro phosphonate residue (pro(P)) at the P-1 site are stable in a pH 7.8 buffer with half-lives of several hours to several days. DPP-IV inhibited by 6, 7 (Ala-Pip(P)(OPh)(2)), 12, or 13 is quite stable, and no enzyme activity was recovered after removal of excess inhibitor and incubation buffer for 1 day. Since the phosphonate inhibitors are specific toward DPP-IV and the inhibited enzymes are stable, they should be useful in establishing the biological functions of DPP-IV and may be useful therapeutically in the prevention of the rejection of transplanted tissue.

  DOI：

  10.1021/jm00049a016
• 作为产物：
  描述：

  亚磷酸三苯酯 、 4-(N-Cbz-(S)-alanyl)aminobutyraldehyde diethyl acetal 在 盐酸 作用下， 生成 Z-Ala-Pro^P(OPh)2
  参考文献：
  名称：

  脯氨酸二苯基膦酸酯的合成新方法

  摘要：

  脯氨酸和相关二肽的膦酸类似物的二苯基酯通过相应的N-取代的4-氨基丁醛与亚磷酸三苯酯的反应来制备。分离非对映异构体，并通过X射线晶体学测定其构型。

  DOI：

  10.1016/0040-4039(95)00586-2