N^α-isobutyloxycarbonyl-Pro-NHNHBoc | 113850-51-4

• 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^α-isobutyloxycarbonyl-Pro-NHNHBoc
• 英文别名: 2-methylpropyl (2S)-2-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 113850-51-4
• 化学式: C₁₅H₂₇N₃O₅
• 分子量: 329.396
• InChiKey: WEIWLPOPMXGBLR-NSHDSACASA-N

物化性质

• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-Alpha-Z-N-ω-tosyl-L-精氨酸环己胺盐 、 H-Pro-NHNH-Boc 以14%的产率得到
  参考文献：
  名称：

  JULIANO, LUIZ;JULIANO, M. A.;DE, MIRANDA A.;TSUBOI, SATOSHI;OKADA, YOSHIO, CHEM. AND PHARM. BULL., 35,(1987) N 6, 2550-2553

  摘要：

  DOI：

文献信息

• Amino acids and peptides. XVI. Synthesis of NG-tosylarginyl peptide derivatives-observation of lactam formation of arginyl residue.
  作者：LUIZ JULIANO、MARIA A. JULIANO、ANTONIO DE MIRANDA、SATOSHI TSUBOI、YOSHIO OKADA

  DOI：10.1248/cpb.35.2550

  日期：——

  Z-Arg (Tos) -Pro-NHNHBoc (1) and Z-Arg (Tos) -Val-NHNHBoc (2) were prepared by the DCC, DCC-HOBt, DCC-DNp, mixed anhydride and DPPA methods. In each coupling reaction, lactam formation from the NG-tosylarginyl residue was observed, although the extent of formation was different depending not only on the carboxyl activation method but also on the kind of amino component. Addition of HOBt suppressed the formation of acylurea but did not suppress the formation of the lactam in the synthesis of 2. Addition of DNp suppressed the formation of the lactam slightly although it did not improve the yield of the target peptides. In the mixed anhydride method, a fairly large amount of the lactam was obtained in the synthesis of Z-Arg (Tos) -Pro-NHNHBoc, and a urethan-type derivative, Nα-isobutyloxycarbonyl-Pro-NHNHBoc, was also formed. However, in the case of synthesis of Z-Arg (Tos) -Val-NHNHBoc, lactam formation was suppressed compared with other activation methods and a small amount of urethan-type derivative was obtained. In both cases, the DPPA method gave a fairly good yield of the target peptide with only a trace amount of lactam formation.

  通过 DCC、DCC-HOBt、DCC-DNp、混合酸酐和 DPPA 方法制备了 Z-Arg (Tos) -Pro-NHNHBoc (1)和 Z-Arg (Tos) -Val-NHNHBoc (2)。在每个偶联反应中，都观察到 NG-对甲苯磺酰精氨酰残基形成内酰胺，但形成的程度不仅取决于羧基活化方法，还取决于氨基成分的种类。在合成 2 的过程中，加入 HOBt 能抑制酰基脲的形成，但不能抑制内酰胺的形成；加入 DNp 能轻微抑制内酰胺的形成，但不能提高目标肽的产量。在混合酸酐法中，合成 Z-Arg (Tos) -Pro-NHNHBoc 时得到了相当多的内酰胺，还形成了一种脲烷型衍生物 Nα-isobutyloxycarbonyl-Pro-NHNHBoc 。然而，在合成 Z-Arg (Tos) -Val-NHNHBoc 时，与其他活化方法相比，内酰胺的形成受到抑制，并获得了少量脲烷型衍生物。在这两种情况下，DPPA 方法都能得到相当高产率的目标肽，而且只有微量内酰胺形成。