2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid | 95863-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid
• 英文别名: N-(benzyloxycarbonyl)-α-dehydrovaline；Cbz-ΔVal-OH；Z-Δ-Val-OH；Z-dehydroVal-OH；3-methyl-2-(phenylmethoxycarbonylamino)but-2-enoic acid
• CAS: 95863-98-2
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: NVFPPWRBEZLYMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid 在 sodium hydroxide 、 氯化亚砜 、 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 2-氧代-3-甲基丁酸
  参考文献：
  名称：

  脱氢寡肽。V.N-羧基α-脱氢氨基酸酸酐的合成及其转化为α-脱氢氨基酸和脱氢寡肽衍生物。

  摘要：

  中文翻译如下： 本文描述了从苄氧羰基-α-去氢氨基酸合成N-羧基α-去氢氨基酸酐（ΔNCA），以及后续将这些产物转化为新的α-去氢氨基酸和去氢低聚肽衍生物的过程。研究发现，新的ΔNCA衍生物对于去氢肽的合成非常有用。本文还讨论了所获得的这些新的去氢低聚肽的消旋行为和构型测定。

  DOI：

  10.1248/cpb.32.3934
• 作为产物：
  描述：

  3-甲基-2-氧代丁酰乙酯 在 lithium hydroxide 、 甲烷磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid
  参考文献：
  名称：

  Asymmetric Hydrogenation of N-Sulfonylated-α-dehydroamino Acids:  Toward the Synthesis of an Anthrax Lethal Factor Inhibitor

  摘要：

  [GRAPHIC]A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-alpha-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.

  DOI：

  10.1021/ol050869s

文献信息

• Design of peptides with α,β-dehydro-residues: synthesis, crystal structure and molecular conformation of a tetrapeptide Z-ΔVal-Val-ΔPhe-Ile-Ome
  作者：J. Makker、S. Dey、S. Mukherjee、R. Vijayaraghavan、P. Kumar、T.P. Singh

  DOI：10.1016/s0022-2860(03)00200-x

  日期：2003.6

  residues. The peptide Z -ΔVal-Val-ΔPhe-Ile-Ome was synthesized in solution phase. Single crystals were grown by slow evaporation from its solution in acetone–water mixture at 25 °C. The crystals belong to an orthorhombic space group P 2 1 2 1 2 1 with a =12.513(2) A, b =15.904(5) A, c =17.686(2) A and Z =4. The structure was determined by direct methods and refined by least-squares procedure to an R factor

  摘要 这是第一个设计的具有支链 β-碳 ΔVal 和 ΔPhe 残基组合的肽。在溶液相中合成肽 Z-ΔVal-Val-ΔPhe-Ile-Ome。通过在 25°C 下从其在丙酮-水混合物中的溶液缓慢蒸发来生长单晶。晶体属于正交空间群 P 2 1 2 1 2 1，a =12.513(2) A, b =15.904(5) A, c =17.686(2) A 和 Z =4。结构通过直接方法确定，并通过最小二乘法细化至 R 因子为 0.082。该肽采用3 10 -螺旋构象，具有两个分子内氢键( i +3→ i )，涉及苯甲氧基的羰基氧原子和ΔPhe和Ile的ΔVal和NH基团，距离为2.764(6)和3.047(7) A ， 分别。结构测定表明，尽管在（ i +2）和（ i +2 ）处存在不利的分支β-碳残基Val和Ile，但在（ i +1）位置具有ΔVal并且在（ i +3）位置具有ΔPhe的四肽采用折叠构象i
• A Convenient Synthesis of Methyl 2-[2-(1-Amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an Important Skeleton of Cyclothiazomycin
  作者：Chung-gi Shin、Akio Ito、Kazuo Okumura、Yutaka Nakamura

  DOI：10.1246/cl.1995.45

  日期：1995.1

  The convenient syntheses of a few methyl 2-(1-amino)alkenyl thiazoline-4-carboxylates and methyl 2-[2-(1-amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate have been accomplished. The latter is an important partial skeleton of macrobicyclic peptide antibiotic cyclothiazomycin.

  一些2-(1-氨基)烯基噻唑啉-4-羧酸甲酯和2-[2-(1-氨基)乙烯基-联噻唑基]噻唑啉-4-羧酸甲酯的简便合成已经完成。后者是大双环肽类抗生素环噻霉素的重要部分骨架。
• Dehydrooligopeptides. XVIII. Enzymatic Hydrolysis and Coupling of Dehydrodipeptide Esters Containing<i>α</i>-Dehydroamino Acid Residue by Using Papain
  作者：Chung-gi Shin、Takeshi Kakusho、Kazushige Arai、Masashi Seki

  DOI：10.1246/bcsj.68.3549

  日期：1995.12

  The enzymatic hydrolysis of N-protected dehydrodipeptide methyl esters (2) (Protect-ΔAA-AA-OMe) was first achieved, despite the requisite of the only neutral and large proteinic l-α-amino acid (AA) in the case using papain. Furthermore, the reverse enzymatic coupling of the C-component 2 with N-component α-amino acid anilides or dehydrodipeptide esters containing dehydrovaline (ΔVal) residue was also successful. Consequently, the present study suggests that the proteolytic enzyme papain is able to become a very useful tool for peptide synthesis by a coupling of the C-component dehydropeptide with N-component α-amino acid, peptide, or dehydropeptide.

  尽管在使用木瓜蛋白酶的情况下，必须使用唯一的中性和大分子蛋白质 l-α-氨基酸（AA），但还是首次实现了 N-保护脱氢二肽甲酯（2）（Protect-ΔAA-AA-OMe）的酶水解。此外，C 组分 2 与含有脱氢缬氨酸（ΔVal）残基的 N 组分 α-氨基酸苯胺或脱氢二肽酯的反向酶偶联也获得了成功。因此，本研究表明，蛋白水解酶木瓜蛋白酶能够通过将 C 组份脱水肽与 N 组份 α-氨基酸、肽或脱水肽偶联，成为一种非常有用的肽合成工具。
• Convenient Syntheses of Thiazoles Incorporated with α-Dehydroamino Acid and Dehydropeptide Structures
  作者：Yutaka Nakamura、Chung-gi Shin、Kazuyuki Umemura、Juji Yoshimura

  DOI：10.1246/cl.1992.1005

  日期：1992.6

  The convenient syntheses of various thiazole α-dehydroamino acids, thiazole valine ethyl ester, and their dehydrodiand tripeptides, which are important moieties and segment of micrococcin P1 and noshiheptide, macrocyclic peptide antibiotics, were first accomplished.

  首次实现了多种噻唑α-脱氢氨基酸、噻唑缬氨酸乙酯及其脱氢二肽和三肽的便捷合成，它们是微球菌P1和noshiheptide、大环肽类抗生素的重要组成部分和片段。
• Design of peptides with α,β-dehydro residues: a dipeptide with a branched β-carbon dehydro residue at the (<i>i</i>+1) position, methyl<i>N</i>-(benzyloxycarbonyl)-α,β-didehydrovalyl-<scp>L</scp>-tryptophanate
  作者：Rangachari Vijayaraghavan、Pravindra Kumar、Sharmistha Dey、Tej P. Singh

  DOI：10.1107/s010827010100840x

  日期：2001.10.15

  The structure of the title peptide, C(25)H(27)N(3)O(5), has been determined and its conformation analysed. Values of the standard peptide torsion angles are phi(1) = -44.2 (3) degrees, psi(1) = 135.9 (2) degrees, phi(2) = -141.6 (2) degrees and psi(2)(T) = 168.0 (2) degrees. The crystal structure is stabilized by an intermolecular hydrogen bond, with an N...O distance of 2.919 (3) A, which is formed between screw-axis-related NH and CO groups of dehydrovaline residues.