N-Phth-Ala-Gly-OH | 1384247-55-5

• 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: N-Phth-Ala-Gly-OH
• 英文别名: 2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)propanoyl]amino]acetic acid
• CAS: 1384247-55-5
• 化学式: C₁₃H₁₂N₂O₅
• 分子量: 276.249
• InChiKey: GVEZFSFPIZJATH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  103.78
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-Phth-Ala-Gly-OH 在 吡啶 、 sodium acetate 、 乙酸酐 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 4-benzylidene-1-methyl-2-(1-phthalimidoethyl)-5-imidazolone
  参考文献：
  名称：

  轻松合成作为荧光蛋白发色团的合成类似物的4-亚芳基-5-咪唑啉酮

  摘要：

  开发了一种简便而有效的合成方法，用于合成各种4-亚芳基-5-咪唑啉酮衍生物。通过N-酰基甘氨酸和芳基醛的Erlenmeyer丁二酸内酯合成来制备4-亚芳基-5-恶唑啉酮。4-亚芳基-5-恶唑啉酮与伯胺的开环反应以优异的产率提供了2-酰基氨基-3-芳基丙烯酰胺。吡啶中2-酰基氨基-3-芳基丙烯酰胺在回流下的新脱水环化反应以良好的收率提供了相应的4-亚芳基-5-咪唑啉酮。

  DOI：

  10.1016/j.tet.2012.04.102
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以90.476%的产率得到
  参考文献：
  名称：

  Site-Selective C(sp³)–H Functionalization of Di-, Tri-, and Tetrapeptides at the N-Terminus

  摘要：

  Although the syntheses of novel and diverse peptides rely mainly on traditional coupling using unnatural amino acids, postsynthetic modification of peptides could provide a complementary method for the preparation of nonproteinogenic peptides. Site selectivity of postsynthetic modification of peptides is usually achieved by targeting reactive moieties, such as the thiol group of cysteine or the C-2 position of tryptophan. Herein, we report the development of site-selective functionalizations of inert C(sp(3))-H bonds of N-terminal amino acids in di-, tri-, and tetrapeptides without installing a directing group. The native amino acid moiety within the peptide is used as a ligand to accelerate the C-H activation reaction. In the long run, this newly uncovered reactivity could provide guidance for developing site-selective C(sp(3))-H activation toward postsynthetic modification of a broader range of peptides.

  DOI：

  10.1021/ja510233h

文献信息

• Palladium(II)-Catalyzed Site-Selective C(sp³ )−H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation
  作者：Tao Liu、Jennifer X. Qiao、Michael A. Poss、Jin-Quan Yu

  DOI：10.1002/anie.201706367

  日期：2017.8.28

  C(sp3)−H alkynylation of oligopeptides was developed with tetrabutylammonium acetate as a key additive. Through molecular design, the acetylene motif served as a linchpin to introduce a broad range of carbonyl‐containing pharmacophores onto oligopeptides, thus providing a chemical tool for the synthesis and modification of novel oligopeptide–pharmacophore conjugates by C−H functionalization. Dipeptide

  以乙酸四丁基铵为关键添加剂，开发了钯 (II) 催化的寡肽 C(sp 3 )−H 炔基化反应。通过分子设计，乙炔基序作为关键，将多种含羰基的药效团引入到寡肽上，从而为通过CH官能化合成和修饰新型寡肽-药效团缀合物提供了化学工具。通过该方法合成了与粪甾烷醇和雌二醇的二肽缀合物，其在向核激素受体过度表达的肿瘤细胞靶向药物递送方面具有潜在的应用。
• Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore
  作者：Cheng-Yu Lee、Yun-Chung Chen、Hao-Chun Lin、Yuandong Jhong、Chih-Wei Chang、Ching-Hua Tsai、Chai-Lin Kao、Tun-Cheng Chien

  DOI：10.1016/j.tet.2012.04.102

  日期：2012.7

  A facile and effective synthesis for a wide variety of 4-arylidene-5-imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the

  开发了一种简便而有效的合成方法，用于合成各种4-亚芳基-5-咪唑啉酮衍生物。通过N-酰基甘氨酸和芳基醛的Erlenmeyer丁二酸内酯合成来制备4-亚芳基-5-恶唑啉酮。4-亚芳基-5-恶唑啉酮与伯胺的开环反应以优异的产率提供了2-酰基氨基-3-芳基丙烯酰胺。吡啶中2-酰基氨基-3-芳基丙烯酰胺在回流下的新脱水环化反应以良好的收率提供了相应的4-亚芳基-5-咪唑啉酮。
• Site-Selective C(sp³)–H Functionalization of Di-, Tri-, and Tetrapeptides at the N-Terminus
  作者：Wei Gong、Guofu Zhang、Tao Liu、Ramesh Giri、Jin-Quan Yu

  DOI：10.1021/ja510233h

  日期：2014.12.3

  Although the syntheses of novel and diverse peptides rely mainly on traditional coupling using unnatural amino acids, postsynthetic modification of peptides could provide a complementary method for the preparation of nonproteinogenic peptides. Site selectivity of postsynthetic modification of peptides is usually achieved by targeting reactive moieties, such as the thiol group of cysteine or the C-2 position of tryptophan. Herein, we report the development of site-selective functionalizations of inert C(sp(3))-H bonds of N-terminal amino acids in di-, tri-, and tetrapeptides without installing a directing group. The native amino acid moiety within the peptide is used as a ligand to accelerate the C-H activation reaction. In the long run, this newly uncovered reactivity could provide guidance for developing site-selective C(sp(3))-H activation toward postsynthetic modification of a broader range of peptides.