Z-Ala-Phol | 102562-48-1

• 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-Phol
• 英文别名: N-Z-L-Ala-L-phenylalaninol；Benzyloxycarbonyl-L-alanyl-L-phenylalaninol；benzyl N-[(2S)-1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 102562-48-1
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: KEQGPNUKYCHVFA-YJBOKZPZSA-N

物化性质

• 熔点：
  118-120.0 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  628.6±55.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Z-Ala-Phol 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到[(S)-1-((S)-4-Benzyl-4,5-dihydro-oxazol-2-yl)-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Solid-phase synthesis of phosphine–oxazoline peptides

  摘要：

  An approach is presented that allows for the synthesis of phosphine-oxazoline ligands by solid-phase synthesis. The method involves the synthesis of amino oxazolines and their use in the cleavage of phosphine sulfide peptides from Kaiser oxime resin. It was discovered that the addition of a catalytic amount of sodium cyanide allows the nucleophilie cleavage from the resin to take place at room temperature and without the addition of acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01596-4
• 作为产物：
  描述：

  (2S)-2-氨基-3-苯丙酸乙酯 在 lithium aluminium tetrahydride 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 生成 Z-Ala-Phol
  参考文献：
  名称：

  753.羰基和生物学上必不可少的取代基之间的相互作用。第五部分：酮对另一系列光学活性氨基衍生物的影响

  摘要：

  DOI：

  10.1039/jr9640003965

文献信息

• Emerimicins III and IV and their ethylalanine12 epimers. Facilitated chemical-enzymatic synthesis and a qualitative evaluation of their solution structures
  作者：Urszula Slomczynska、Denise D. Beusen、Janusz Zabrocki、Karol Kociolek、Adam Redlinski、Fritz Reusser、William C. Hutton、Miroslaw T. Leplawy、Garland R. Marshall

  DOI：10.1021/ja00037a010

  日期：1992.5

  The peptaibol antibiotics, emerimicin III and IV (Ac-Phe 1 -MeA 2 -MeA 3 -MeA 4 -Val 5 -Gly 6 -Leu 7 -MeA 8 -MeA 9 - Hyp 10 -Gln 11 -R-EtA 12 -Hyp 13 -Xxx 14 -Phol 15 , where Xxx=Ala for emerimicin III and Xxx=MeA for emerimicin IV) and their EtA 12 epimers have been synthesized using a combined approach involving solution-phase fragment condensation with a final papain-mediated coupling of the 1-6

  peptaibol 抗生素，emerimicin III 和 IV（Ac-Phe 1 -MeA 2 -MeA 3 -MeA 4 -Val 5 -Gly 6 -Leu 7 -MeA 8 -MeA 9 - Hyp 10 -Gln 11 -R-EtA 12 -Hyp 13 -Xxx 14 -Phol 15 ，其中 Xxx=Ala for emerimicin III 和 Xxx=MeA for emerimicin IV) 和它们的 EtA 12 差向异构体已经使用包括溶液相片段缩合和最终木瓜蛋白酶介导的偶联的组合方法合成1-6 和 7-15 片段
• An efficient method for the preparation of peptide alcohols
  作者：Alan Roy Katritzky、Nader Elmaghwry Abo-Dya、Srinivasa Rao Tala、Kapil Gyanda、Zakaria Kamel Abdel-Samii

  DOI：10.1039/b905730g

  日期：——

  N -Protected LL-dipeptide alcohols 3a–p, diastereomeric mixture (3d + 3d′) and tripeptide alcohols 6a–c were synthesized by treatment of various amino alcohols with N-protected(α-aminoacyl)benzotriazoles 1a–c, 1f–m, (1a + 1a′) and N-protected(α-dipeptidoyl)benzotriazoles 5a, 5b respectively in good yields with complete retention of chirality.

  氮 -通过用N-保护的(α-氨基酰基)苯并三唑1a-c、1f-m处理各种氨基醇合成受保护的LL-二肽醇3a-p、非对映体混合物(3d + 3d')和三肽醇6a-c， (1a + 1a') 和 N-保护的(α-二肽酰基)苯并三唑 5a、5b 分别具有良好的产率，并且完全保留了手性。
• MARSHALL, GARLAND R.;CLARK, JOHN D.;DUNBAR, JAMES B. (JR);SMITH, G. DAVID+, INT. J. PEPTIDE AND PROTEIN RES., 32,(1988) N, C. 544-555
  作者：MARSHALL, GARLAND R.、CLARK, JOHN D.、DUNBAR, JAMES B. (JR)、SMITH, G. DAVID+

  DOI：——

  日期：——
• 753. Interaction between carbonyl groups and biologically essential substituents. Part V. The effect of ketones on further series of optically active amino-derivatives
  作者：F. Bergel、Margaret A. Peutherer

  DOI：10.1039/jr9640003965

  日期：——
• Solid-phase synthesis of phosphine–oxazoline peptides
  作者：Scott R. Gilbertson、Ping Lan

  DOI：10.1016/s0040-4039(02)01596-4

  日期：2002.9

  An approach is presented that allows for the synthesis of phosphine-oxazoline ligands by solid-phase synthesis. The method involves the synthesis of amino oxazolines and their use in the cleavage of phosphine sulfide peptides from Kaiser oxime resin. It was discovered that the addition of a catalytic amount of sodium cyanide allows the nucleophilie cleavage from the resin to take place at room temperature and without the addition of acid. (C) 2002 Elsevier Science Ltd. All rights reserved.