Cbz,PMB-Phe-OH | 439589-22-7

• 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: Cbz,PMB-Phe-OH
• CAS: 439589-22-7
• 化学式: C₂₅H₂₅NO₅
• 分子量: 419.477
• InChiKey: MHBQWNPVKCWKOM-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Cbz,PMB-Phe-OH 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 、 (叔丁基亚氨基)三(吡咯烷)膦 、 methyloxirane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0~85.0 ℃ 、103.42 kPa 条件下， 反应 49.0h， 生成 (S)-α-benzylaspartic acid
  参考文献：
  名称：

  General Approach for the Stereocontrolled Construction of the β-Lactam Ring in Amino Acid-Derived 4-Alkyl-4-carboxy-2-azetidinones

  摘要：

  The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the beta-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding N-alpha-chloroacetyl derivatives bearing (+)- or (-)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).

  DOI：

  10.1021/jo025571j
• 作为产物：
  描述：

  N-<4-Methoxy-benzyliden>-phenylalanin 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 反应 1.67h， 生成 Cbz,PMB-Phe-OH
  参考文献：
  名称：

  The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1

  摘要：

  The rationale for targeting the human di-/tripeptide transporter hPEPT1 for oral drug delivery has been well established by several drug and prodrug cases. The aim of this study was to synthesize novel ketomethylene modified tripeptidomimetics and to investigate their binding affinity for hPEPT1. Three related tripeptidomimetics of the structure H-Phe-psi[COCH2]-Ser(Bz)-X-aa-OH were synthesized applying the tandem chain extension aldol reaction, where amino acid derived beta-keto imides were stereoselectively converted to alpha-substituted gamma-keto imides. In addition, three corresponding tripeptides, composed of amide bonds, were synthesized for comparison of binding affinities. The six investigated compounds were all defined as high affinity ligands (K-i-values < 0.5 mM) for hPEPT1 by measuring the concentration dependent inhibition of apical [C-14]Gly-Sar uptake in Caco-2 cells. Consequently, the ketomethylene replacement for the natural amide bond and alpha-side chain modifications appears to offer a promising strategy to modify tripeptidic structures while maintaining a high affinity for hPEPT1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.108