2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-acrylic acid | 86810-05-1

• 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: 2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-acrylic acid
• 英文别名: Boc-Ala-Dha methyl ester
• CAS: 86810-05-1
• 化学式: C₁₁H₁₈N₂O₅
• 分子量: 258.274
• InChiKey: HGZVIFJZYNJYLA-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-acrylic acid 在 sodium methylate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 水 为溶剂， 生成 (S)-1-[2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-acryloyl]-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Model studies of lantibiotic biogenesis

  摘要：

  A six residue polypeptide has been synthesized to study the proposed biosynthesis of lanthionine. It is shown that this peptide spontaneously cyclizes in a biomimetic fashion via a completely stereoselective intramolecular Michael addition to form (2S, 6R)-lanthionine, as found in naturally occurring Iantibiotics.

  DOI：

  10.1016/s0040-4039(00)61488-0
• 作为产物：
  描述：

  N-Boc-alanyldidehydroalanine ethyl ester 在 saponification 作用下， 以78%的产率得到2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-acrylic acid
  参考文献：
  名称：

  Model studies of lantibiotic biogenesis

  摘要：

  A six residue polypeptide has been synthesized to study the proposed biosynthesis of lanthionine. It is shown that this peptide spontaneously cyclizes in a biomimetic fashion via a completely stereoselective intramolecular Michael addition to form (2S, 6R)-lanthionine, as found in naturally occurring Iantibiotics.

  DOI：

  10.1016/s0040-4039(00)61488-0

文献信息

• Chemoselective Installation of Amine Bonds on Proteins through Aza-Michael Ligation
  作者：Allyson M. Freedy、Maria J. Matos、Omar Boutureira、Francisco Corzana、Ana Guerreiro、Padma Akkapeddi、Víctor J. Somovilla、Tiago Rodrigues、Karl Nicholls、Bangwen Xie、Gonzalo Jiménez-Osés、Kevin M. Brindle、André A. Neves、Gonçalo J. L. Bernardes

  DOI：10.1021/jacs.7b10702

  日期：2017.12.20

  method is demonstrated for three proteins and is shown to be fully compatible with disulfide bridges, as evidenced by the selective modification of recombinant albumin that displays 17 structurally relevant disulfides. The practicability and utility of our approach is further demonstrated by the construction of a chemically modified C2A domain of Synaptotagmin-I protein that retains its ability to preferentially

  蛋白质的化学修饰对于各种重要的诊断和治疗应用至关重要。迄今为止开发的许多策略缺乏化学和区域选择性，并导致非天然连接可能在体内不稳定并对蛋白质的结构和功能产生不利影响。我们在这里描述了 N-亲核试剂在蛋白质上下文中与氨基酸脱氢丙氨酸 (Dha) 的反应。当 Dha 以化学方式安装在蛋白质中时，添加范围广泛的 N-亲核试剂能够在温和的生物相容性条件下以化学选择性的方式快速形成胺键（二级和三级）。这些新的键在很宽的 pH 值范围（pH 2.8 至 12.8）、还原条件（生物硫醇，如谷胱甘肽）和人血浆中都是稳定的。这种方法对三种蛋白质进行了证明，并显示出与二硫键完全兼容，如重组白蛋白的选择性修饰所证明的那样，显示 17 种结构相关的二硫键。我们的方法的实用性和实用性通过构建 Synaptotagmin-I 蛋白的化学修饰 C2A 结构域得到进一步证明，该结构域保留其优先结合凋亡细胞的能力，其水平与
• Inhibition of the mammalian .beta.-lactamase renal dipeptidase (dehydropeptidase-I) by Z-2-(acylamino)-3-substituted-propenoic acids
  作者：Donald W. Graham、Wallace T. Ashton、Louis Barash、Jeannette E. Brown、Ronald D. Brown、Laura F. Canning、Anna Chen、James P. Springer、Edward F. Rogers

  DOI：10.1021/jm00389a018

  日期：1987.6

  The title enzyme deactivates the potent carbapenem antibiotic imipenem in the kidney, producing low antibiotic levels in the urinary tract. A series of (Z)-2-(acylamino)-3-substituted-propenoic acids (3) are specific, competitive inhibitors of the enzyme capable of increasing the urinary concentration of imipenem in vivo. Many of the compounds were prepared in one step from an alpha-keto acid and a primary amide. The optimum R2 groups are 2,2-dimethyl, -dichloro, and -dibromocyclopropyl. With R2 = 2,2-dimethylcyclopropyl (DMCP), a wide variety of R3 groups including alkyl, oxa- and thiaalkyl, and alkyl groups containing acidic, basic, and neutral substituents give effective inhibitors with Ki values of 0.02-1 microM and a range of pharmacokinetic properties. By resolution of enantiomers and X-ray crystallography, the enzyme-inhibitory activity of the DMCP group was found to reside with the 1S isomer. The cysteinyl compound 176 (cilastatin, MK-0791) has the desired pharmacological properties and has been chosen for combination with imipenem.