Ac-Leu-Ala-OH | 91211-88-0

• 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: Ac-Leu-Ala-OH
• 英文别名: N-Acetyl-L-leucyl-L-alanine；(2S)-2-[[(2S)-2-acetamido-4-methylpentanoyl]amino]propanoic acid
• CAS: 91211-88-0
• 化学式: C₁₁H₂₀N₂O₄
• 分子量: 244.291
• InChiKey: IVVOEMXWWNFLLC-CBAPKCEASA-N

物化性质

• 沸点：
  531.5±35.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ac-Leu-Ala-OH 、 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Novel Glycopeptidomimetics ContainingO- andN-Glycosylated α-Aminooxy Acids by Fragment Coupling on Solid Support

  摘要：

  新型的糖基化拟肽分子，具备O-和N-糖基化的α-氨基氧酸，通过固相支持的片段偶联高效合成。在溶液中制备的N-端糖基化三肽模拟物，在O-(7-氮杂苯并三唑-1-基)-1,1,3,3-四甲基脲六氟磷酸酯(HATU)/1-羟基-7-氮杂苯并三唑(HOAt)/N-乙基吗啉(NEM)条件下，与连接在树脂上的C-端二肽偶联。

  DOI：

  10.1055/s-2002-33509

文献信息

• Asymmetric Synthesis of Silanediol Inhibitors for the Serine Protease Coagulation Cascade Enzyme FXIa
  作者：Hoan Q. Duong、Scott McN. Sieburth

  DOI：10.1021/acs.joc.8b00116

  日期：2018.5.18

  Silanediol peptidomimetics have been prepared, designed to inhibit the serine protease enzyme Factor XIa (FXIa) for treatment of thrombosis without complete interruption of normal hemostasis. These Arg-[Si]-Ala analogues of the FXIa substrate (FIX) are the first silanediol dipeptide analogues to carry a basic guanidine group. Control of stereochemistry was accomplished using catalytic asymmetric hydrosilylation

  已经制备了硅烷二醇拟肽，其旨在抑制丝氨酸蛋白酶Xa因子（FXIa）以治疗血栓形成而不会完全中断正常止血。FXIa底物（FIX）的这些Arg- [Si] -Ala类似物是第一个带有碱性胍基的硅烷二醇二肽类似物。立体化学的控制是通过催化不对称氢化硅烷化反应和在Davis-Ellman磺胺亚胺中添加甲硅烷基锂中间体实现的。
• Synthesis and testing of azaglutamine derivatives as inhibitors of Hepatitis A Virus (HAV) 3C proteinase
  作者：Y Huang

  DOI：10.1016/s0968-0896(99)00006-1

  日期：1999.4

  Hepatitis A virus (HAV) 3C proteinase is a picornaviral cysteine proteinase that is essential for cleavage of the initially synthesized viral polyprotein precursor to mature fragments and is therefore required for viral replication in vivo. Since the enzyme generally recognizes peptide substrates with L-glutamine at the P-1 site, four types of analogues having an azaglutamine residue were chemically synthesized: hydrazo-o-nitrophenylsulfenamides A (e.g. 16); frame-shifted hydrazo-o-nitrophenylsulfenamides B (e.g. 25-28); the azaglutamine sulfonamides C (e.g. 7, 8, 11, 12); and haloacetyl azaglutamine analogues 2 and 3. Testing of these compounds for inhibition of the HAV 3C proteinase employed a C24S mutant in which the non-essential surface cysteine was replaced with serine and which displays identical catalytic parameters to the wild-type enzyme. Sulfenamide 16 (type A) showed no significant inhibition. Sulfenamide 27 (type B) had an IC50 of ca 100 mu M and gave time-dependent inactivation of the enzyme due to disulfide bond formation with the active site cysteine thiol, as demonstrated by electrospray mass spectrometry. Sulfonamide 8 (type C) was a weak competitive inhibitor with an IC50 of approximately 75 mu M. The haloacetyl azaglutamine analogues 2 and 3 were time-dependent irreversible inactivators of HAV 3C proteinase with rate constants k(obs)[I] of 680 M-1 s(-1) and 870 M-1 s(-1), respectively, and were shown to alkylate the active site thiol. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of Novel Glycopeptidomimetics Containing<i>O</i>- and<i>N</i>-Glycosylated α-Aminooxy Acids by Fragment Coupling on Solid Support
  作者：Injae Shin、Myung-ryul Lee、Jiyong Lee

  DOI：10.1055/s-2002-33509

  日期：——

  New glycosylated peptidomimetics possessing O- and N-glycosylated α-aminooxy acids were efficiently synthesized by fragment coupling on solid support. The N-terminal glycosylated tripeptide mimics prepared in solution were coupled to the C-terminal dipeptides attached to the resin under O-(7-azabenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU)/1-hydroxy-7-azabenzotriazole (HOAt)/N-ethylmorpholin (NEM) conditions.

  新型的糖基化拟肽分子，具备O-和N-糖基化的α-氨基氧酸，通过固相支持的片段偶联高效合成。在溶液中制备的N-端糖基化三肽模拟物，在O-(7-氮杂苯并三唑-1-基)-1,1,3,3-四甲基脲六氟磷酸酯(HATU)/1-羟基-7-氮杂苯并三唑(HOAt)/N-乙基吗啉(NEM)条件下，与连接在树脂上的C-端二肽偶联。