Boc-Gly-ΔAla | 50333-24-9

• 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: Boc-Gly-ΔAla
• 英文别名: 2-[[2-[(2-Methylpropan-2-yl)oxycarbonylamino]acetyl]amino]prop-2-enoic acid；2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]prop-2-enoic acid
• CAS: 50333-24-9
• 化学式: C₁₀H₁₆N₂O₅
• 分子量: 244.247
• InChiKey: UKIOOLJRTVTLBT-UHFFFAOYSA-N

物化性质

• 沸点：
  509.8±50.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Gly-ΔAla 在 1-羟基苯并三唑 作用下， 反应 24.0h， 生成 methyl {2-[(tert-butoxycarbonylamino)acetamido]prop-2-enamido}acetate
  参考文献：
  名称：

  Conformation oftert-butoxycarbonylglycyl-dehydroalanyl-glycine methyl ester in the crystalline state and calculated in the gas phase

  摘要：

  tert-Butoxycarbonylglycyl-dehydroalanyl-glycine methyl ester ( systematic name: methyl {2-[(tert-butoxycarbonylamino)acetamido] prop-2-enamido}acetate) (Boc(0)-Gly(1)-Delta Ala(2)-Gly(3)-OMe), C13H21N3O6, has been structurally characterized by single-crystal X- ray diffraction and by density functional theory (DFT) calculations at the B3LYP/6-311+G** level. The peptide chain in both the solid-state and calculated structures adopts neither beta nor gamma turns. All amino acid residues in the tripeptide sequence are linked trans to each other. The bond lengths and valence angles of the amino acid units in the crystal structure and gas phase are comparable. However, the conformation of the third glycyl residue (Gly(3)) is different in the crystalline state and in the gas phase. It is stabilized in the calculated structure by an additional intramolecular short contact between Gly(3) NH and methyl ester COMe groups.

  DOI：

  10.1107/s0108270106052590
• 作为产物：
  描述：

  (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester 生成 Boc-Gly-ΔAla
  参考文献：
  名称：

  Gross,E. et al., Angewandte Chemie, 1973, vol. 85, p. 672 - 673

  摘要：

  DOI：

文献信息

• Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
  作者：Maciej Makowski、Paweł Lenartowicz、Bartosz Oszywa、Michał Jewgiński、Małgorzata Pawełczak、Paweł Kafarski

  DOI：10.1007/s00044-015-1366-0

  日期：2015.8

  The procedures for the synthesis of esters of dehydropeptides containing C-terminal (Z)-dehydrophenylalanine and dehydroalanine have been elaborated. These esters appeared to be moderate or weak inhibitors of cathepsin C, with some of them exhibiting slow-binding behavior. As shown by molecular modeling, they are rather bound at the surface of the enzyme and are not submersed in its binding cavities

  已经阐述了合成含有C-末端（Z）-脱氢苯丙氨酸和脱氢丙氨酸的脱氢肽的酯的方法。这些酯似乎是组织蛋白酶C的中度或弱抑制剂，其中一些表现出缓慢的结合行为。如分子模型所示，它们相当地结合在酶的表面，并且没有浸入其结合腔中。
• Synthesis of Tetrapeptides Containing Dehydroalanine, Dehydrophenylalanine and Oxazole as Building Blocks for Construction of Foldamers and Bioinspired Catalysts
  作者：Paweł Lenartowicz、Maarten Beelen、Maciej Makowski、Weronika Wanat、Błażej Dziuk、Paweł Kafarski

  DOI：10.3390/molecules27092611

  日期：——

  structure and additionally enables the introduction of non-typical side-chain substituents. Thus, such compounds could be building blocks for obtaining novel foldamers and/or artificial enzymes (artzymes). In this paper, effective synthetic procedures leading to such building blocks—tetrapeptides containing glycyldehydroalanine, glycyldehydrophenylalanine, and glycyloxazole subunits—are described. Peptides

  将脱氢氨基酸或恶唑片段掺入肽链伴随着扭曲的三维结构，并且还能够引入非典型的侧链取代基。因此，这些化合物可以成为获得新折叠体和/或人工酶（artzymes）的构件。在本文中，描述了产生这种结构单元的有效合成程序——含有甘氨酰脱氢丙氨酸、甘氨酰脱氢苯丙氨酸和甘氨酰恶唑亚基的四肽。含有丝氨酸的肽被用作底物，用于将它们转化为含有脱氢丙氨酸和氨基甲基恶唑-4-羧酸的肽，同时考虑在合成的最后步骤将这些片段引入长链肽的可能要求。
• Makowski, Maciej; Rzeszotarska, Barbara; Kubica, Zbigniew, Liebigs Annalen der Chemie, 1986, # 6, p. 980 - 991
  作者：Makowski, Maciej、Rzeszotarska, Barbara、Kubica, Zbigniew、Pietrzynski, Grzegorz、Hetper, Jacek

  DOI：——

  日期：——
• Pawelczak,K. et al., Polish Journal of Chemistry, 1979, vol. 53, p. 2003 - 2011
  作者：Pawelczak,K. et al.

  DOI：——

  日期：——
• Makowski, Maciej; Rzeszotarska, Barbara; Zbigniew, Kubica, Liebigs Annalen der Chemie, 1985, # 5, p. 893 - 900
  作者：Makowski, Maciej、Rzeszotarska, Barbara、Zbigniew, Kubica、Pietrzynski, Grzegorz

  DOI：——

  日期：——