Val-Gly-OEt*HCl | 28836-83-1

• 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: Val-Gly-OEt*HCl
• 英文别名: ethyl 2-[[(2S)-2-amino-3-methylbutanoyl]amino]acetate;hydrochloride
• CAS: 28836-83-1
• 化学式: C₉H₁₈N₂O₃*ClH
• 分子量: 238.714
• InChiKey: WRRTURKJTJMLCM-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  81.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Val-Gly-OEt*HCl 在 sodium hydroxide 、 Biorex 70 resin 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-t-butoxycarbonylglycyl-L-valylglycine
  参考文献：
  名称：

  Dutta, Anand S.; Giles, Michael B.; Williams, Joseph C., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1655 - 1664

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[N-formyl-L-valyl=>glycine ethyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 Val-Gly-OEt*HCl
  参考文献：
  名称：

  Orlowska, Alicja; Drabarek, Stefania, Polish Journal of Chemistry, 1980, vol. 54, # 11/12, p. 2329 - 2336

  摘要：

  DOI：

文献信息

• 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one as a New Protecting Reagent in Peptide Synthesis
  作者：M. G. Gorbunova、I. I. Gerus、S. V. Galushko、V. P. Kukhar

  DOI：10.1055/s-1991-26420

  日期：——

  The 4,4,4-trifluoro-3-oxo-1-butenyl group is proposed as a suitable protecting group for the protection of the N-H terminal of amino acids in peptide synthesis. Amino acids react with 4-ethoxy-1,1,1-trifluoro-3-buten-2-one to give the N-protected amino acids, the protecting group can be removed by acidic hydrolysis. The formation of peptide bonds using on N-4,4,4-trifluoro-3-oxo-1-butenyl protected amino acids occurs without racemization.

  提出4,4,4-三氟-3-氧代-1-丁烯基作为在肽合成中保护氨基酸N-H末端的合适保护基团。氨基酸与4-乙氧基-1,1,1-三氟-3-丁烯-2-酮反应生成N-保护的氨基酸，该保护基团可以通过酸性水解去除。使用N-4,4,4-三氟-3-氧代-1-丁烯基保护的氨基酸形成肽键时不会发生消旋化。
• Cleavage of unactivated amide bonds by ammonium salt-accelerated hydrazinolysis
  作者：Yuhei Shimizu、Megumi Noshita、Yuri Mukai、Hiroyuki Morimoto、Takashi Ohshima

  DOI：10.1039/c4cc02014f

  日期：——

  Hydrazinolysis of unactivated amide bonds is significantly accelerated by the addition of ammonium salts. The reactions proceed at 50-70 degrees C to give amines with broad substrate scope that outperforms existing amide bond cleavage reactions. Application to peptide and amino sugar derivatives is also demonstrated.

  铵盐的加入大大促进了未活化酰胺键的水合肼解反应。反应在50-70摄氏度下进行，得到的胺具有较宽的底物范围，胜过现有的酰胺键裂解反应。还证明了对肽和氨基糖衍生物的应用。
• Stimulus Responsive Behavior of Elastin-Based Side Chain Polymers
  作者：Lee Ayres、Kaspar Koch、P. Hans H. M. Adams, and、Jan C. M. van Hest

  DOI：10.1021/ma047923p

  日期：2005.3.1

  this series of elastin based side chain block copolymers was investigated by changing the degree of polymerization, polymer concentration, and pH. The effects of these parameters on the LCST of the side chain block copolymers were similar when compared with linear poly(VPGVG). The aggregates which were formed above the transition temperature were investigated using light scattering and cryo-SEM techniques

  多年来，线性聚（VPGVG）作为结构蛋白弹性蛋白的模型已被广泛研究。弹性蛋白的特征在于较低的临界溶液温度（LCST）。该LCST可能受几个因素的影响，主要是分子量，浓度和pH值。使用原子转移自由基聚合（ATRP）合成ABA型嵌段共聚物，其中VPGVG序列位于A嵌段的侧链中，而B嵌段为聚乙二醇（PEG）。通过改变聚合度，聚合物浓度和pH值，研究了这一系列基于弹性蛋白的侧链嵌段共聚物的LCST行为。与线性聚（VPGVG）相比，这些参数对侧链嵌段共聚物的LCST的影响是相似的。
• Umpolung Ala ^B Reagents for the Synthesis of Non‐Proteogenic Amino Acids, Peptides and Proteins**
  作者：Feng Zhu、Eric Miller、Wyatt C. Powell、Kelly Johnson、Alexander Beggs、Garrett E. Evenson、Maciej A. Walczak

  DOI：10.1002/anie.202207153

  日期：2022.8

  A novel amino acid synthon in the form of boronoalanine (AlaB) suitable for umpolung peptide/protein functionalization is described. It is demonstrated that AlaB can be incorporated into peptides and proteins, and remains stable under solid-phase synthesis, native chemical ligation, and radical desulfurization. Furthermore, AlaB is a competent partner in inter(intra)molecular C(sp3)−C(sp2) cross-couplings

  描述了一种适用于 umpolung 肽/蛋白质功能化的硼丙氨酸 (Ala B )形式的新型氨基酸合成子。结果表明，Ala B可以掺入肽和蛋白质中，并且在固相合成、天然化学连接和自由基脱硫下保持稳定。此外，Ala B是分子间（内）C( sp 3 )−C( sp 2 ) 交叉偶联的有效伙伴。
• Rhodium(III)-Catalyzed C–H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides
  作者：Jingjing Peng、Chunpu Li、Mirzadavlat Khamrakulov、Jiang Wang、Hong Liu

  DOI：10.1021/acs.orglett.0c00086

  日期：2020.2.21

  Maleimide is widely applied in many fields, especially in antibody-drug conjugations and peptide drugs. Herein, we develop a strategy for the C-H alkenylation of tryptophan and tryptophan-containing peptides, providing a synthetic route of decorating maleimide on peptides. The method has a high tolerance of functional groups and protecting groups. Furthermore, this method was applied to prepare peptide conjugation with molecules such as drugs and fluorescence probes. Moreover, macrocyclic peptides were obtained via this reaction.