L-酪氨酰-D-丙氨酰甘氨酰-N-[2-氨基-4-(甲基亚硫酰基<亚磺酰>)丁酰]-L-苯丙氨酸酰胺 | 90068-06-7

• 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
• 中文名称: L-酪氨酰-D-丙氨酰甘氨酰-N-[2-氨基-4-(甲基亚硫酰基&lt亚磺酰&gt)丁酰]-L-苯丙氨酸酰胺
• 英文名称: proline isobutylamide
• 英文别名: (S)-N-isobutylpyrrolidine-2-carboxamide；pyrrolidine-2-carboxylic acid isobutylamide；(2S)-N-(2-methylpropyl)pyrrolidine-2-carboxamide
• CAS: 90068-06-7
• 化学式: C₉H₁₈N₂O
• 分子量: 170.255
• InChiKey: BXSADHSYWIGZJV-QMMMGPOBSA-N

物化性质

• 沸点：
  329.8±31.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-酪氨酰-D-丙氨酰甘氨酰-N-[2-氨基-4-(甲基亚硫酰基<亚磺酰>)丁酰]-L-苯丙氨酸酰胺 在 氢溴酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(S)-2-((S)-2-Isobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-succinamic acid
  参考文献：
  名称：

  Kasafirek, Evzen; Fric, Premysl; Slaby, Jan, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 12, p. 3034 - 3041

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 N-乙基哌啶 、 氢溴酸 、 氯甲酸乙酯 作用下， 以 溶剂黄146 为溶剂， 生成 L-酪氨酰-D-丙氨酰甘氨酰-N-[2-氨基-4-(甲基亚硫酰基<亚磺酰>)丁酰]-L-苯丙氨酸酰胺
  参考文献：
  名称：

  Kasafirek, Evzen; Fric, Premysl; Slaby, Jan, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 12, p. 3034 - 3041

  摘要：

  DOI：

文献信息

• Direct amidation of unprotected amino acids using B(OCH₂CF₃)₃
  作者：Rachel M. Lanigan、Valerija Karaluka、Marco T. Sabatini、Pavel Starkov、Matthew Badland、Lee Boulton、Tom D. Sheppard

  DOI：10.1039/c6cc05147b

  日期：——

  A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of [small alpha]-amino acids with a range of amines in cyclopentyl methyl ether. The method can...

  可商购的硼酸酯B（OCH 2 CF 3）3可用于在环戊基甲基醚中实现小α-氨基酸与一系列胺的无保护基的直接酰胺化。该方法可以...
• Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
  作者：Marco T. Sabatini、Valerija Karaluka、Rachel M. Lanigan、Lee T. Boulton、Matthew Badland、Tom D. Sheppard

  DOI：10.1002/chem.201800372

  日期：2018.5.11

  Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also

  已使用多种“经典”偶联剂，化学计量或催化基团（IV）金属盐和硼路易斯酸研究了未保护氨基酸的酰胺化。通过尝试合成衍生自二十种天然和几种非天然氨基酸以及广泛选择的伯胺和仲胺的酰胺，探索了反应的范围。该研究还研究了药用相关化合物的合成，以及这种直接酰胺化方法的可扩展性。最后，我们提供了对在这些反应中观察到的化学选择性的见解。
• Compounds Binding to the S2−S3 Pockets of Thrombin
  作者：Mikael Nilsson、Markku Hämäläinen、Maria Ivarsson、Johan Gottfries、Yafeng Xue、Sebastian Hansson、Roland Isaksson、Tomas Fex

  DOI：10.1021/jm8011849

  日期：2009.5.14

  A set of compounds designed to bind to the S2-S3 pockets of thrombin was prepared. These compounds included examples with no interactions in the S1 pocket. Proline, a common P2 in many thrombin inhibitors, was combined with known P3 residues and P1 substituents of varying size and lipophilicity. Binding constants were determined using surface plasmon resonance (SPR) biosensor technology and were found to be in good agreement with results from an enzyme assay. A dramatic increase in affinity (100-1000 times) was seen for compounds incorporating an amino group capable of forming a hydrogen bond with gly216 in the protein backbone. The ligand efficiency was increased by including substituents that form stronger hydrophobic interactions with the P1 pocket. The binding mode was confirmed by X-ray analysis, which revealed the anticipated binding motif that included hydrogen bonds as well as a tightly bound water molecule. A QSAR model indicated that hydrogen bonding and lipophilicity were important for the prediction of binding constants. The results described here may have implications for how directed compound libraries for shallow protein pockets, like S2 and S3 in serine proteases, can be designed.
• Amino acid derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0346847B1

  公开（公告）日：1994-05-11
• KASAFIREK, EVZEN;FRIC, PREMYSL;SLABY, JAN;KOCNA, PETR, COLLECT. CZECHOSL. CHEM. COMMUN., 52,(1987) N 12, 3034-3041
  作者：KASAFIREK, EVZEN、FRIC, PREMYSL、SLABY, JAN、KOCNA, PETR

  DOI：——

  日期：——