Z-(S)-Ala-(S)-Pro-OBzl | 23458-22-2

• 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-(S)-Ala-(S)-Pro-OBzl
• 英文别名: Cbz-Ala-Pro-OBzl；Z-Ala-Pro-OBzl；benzyl (2S)-1-[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylate
• CAS: 23458-22-2
• 化学式: C₂₃H₂₆N₂O₅
• 分子量: 410.47
• InChiKey: IWRBJXAOSITEJE-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 在 2,4,6-三甲基吡啶 、 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 Z-(S)-Ala-(S)-Pro-OBzl
  参考文献：
  名称：

  Amino Acids and Peptides; 67.¹Easy Preparation and Use of Benzyloxycarbonyl Derivatives of Amino Acid Chlorides and α-Hydroxycarboxylic Acid Chlorides

  摘要：

  N-苄氧羰基氨基酸氯化物和α-苄氧羰氧基羧酸氯化物可以通过将相应的羧酸与1-氯-N，N，2-三甲基-1-丙烯-1-胺反应而容易地制备。它们可以直接与O、N和C亲核试剂反应，生成肽、酮和酯。

  DOI：

  10.1055/s-1988-27612

文献信息

• Incorporation of unnatural amino acid derivatives into a peptide bond via an oxime ester catalysed by papain or lipase
  作者：Shui-Tein Chen、Chin-Far Tsai、Kung-Tsung Wang

  DOI：10.1039/cc9960000165

  日期：——

  In the presence of an oxime in the reaction solution, papain and lipase P (Pseudomonas from Amano) catalysed the stereoselective transesterification of an N-protected amino acid or peptide ester to form an active (oxime) ester which in turn underwent peptide bond formation with several natural and unnatural amino acid derivatives (proline, N-methylglycine, N-methylalanine, α-methylphenylalanine).

  在反应溶液中存在肟的情况下，木瓜蛋白酶和脂肪酶 P（天野假单胞菌）催化 N 保护氨基酸或肽酯的立体选择性酯交换反应，形成活性（肟）酯，活性酯又与几种天然和非天然氨基酸衍生物（脯氨酸、N-甲基甘氨酸、N-甲基丙氨酸、α-甲基苯丙氨酸）形成肽键。
• Chemo-Enzymatic Synthesis of Optically Active Amino Acids and Peptides
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1002/jccs.199900046

  日期：1999.6

  AbstractThe industrial alkaline protease, alcalase, is stable and active in a high concentration of organic solvents and useful as a biocatalyst for (i) diastereoselective hydrolysis of peptide esters and preparation of racemization‐free peptides; (ii) selective incorporation of esters of D‐amino acid into peptides in t‐butanol via a selective hydrolysis of esters of D,L‐amino acid, followed by using the unhydrolyzed D‐esters as a nucleophile in a kinetically controlled peptide bond formation; (iii) resolution of esters of amino acid in 95% t‐butanol/5% water, followed by saponification of the unreacted esters to offer both enantiomers with high yield and optical purity; (iv) completely resolve amino‐acid esters with high yield and optical purity via in situ racemization of the unreacted antipode catalyzed by pyridoxal 5‐phosphate; (v) cryobioorganic synthesis of peptides with increased yields 15%–40% of peptide bond formation by reaction at 5 °C instead of 25–30 °C of a kinetically controlled enzymatic reaction in alcohols.
• Amino Acids and Peptides; 67.¹Easy Preparation and Use of Benzyloxycarbonyl Derivatives of Amino Acid Chlorides and α-Hydroxycarboxylic Acid Chlorides
  作者：Ulrich Schmidt、Matthias Kroner、Ulrich Beutler

  DOI：10.1055/s-1988-27612

  日期：——

  N-Benzyloxycarbonyl amino acid chlorides and α-benzyloxycarbonyloxy carboxylic acid chlorides are readily available by treating the corresponding carboxylic acids with 1-chloro-N,N,2-trimethyl-1-propen-1-amine. They can be immediately reacted with O-, N- and C-nucleophiles to afford peptides, ketones and esters.

  N-苄氧羰基氨基酸氯化物和α-苄氧羰氧基羧酸氯化物可以通过将相应的羧酸与1-氯-N，N，2-三甲基-1-丙烯-1-胺反应而容易地制备。它们可以直接与O、N和C亲核试剂反应，生成肽、酮和酯。