Boc-Val-Asp(OBzl)-OBzl | 70853-19-9

• 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-Val-Asp(OBzl)-OBzl
• 英文别名: Boc-Val-Asp(OBzl)2；Boc-Val-Asp(OBn)-OBn；dibenzyl (2S)-2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]butanedioate
• CAS: 70853-19-9
• 化学式: C₂₈H₃₆N₂O₇
• 分子量: 512.603
• InChiKey: RRRJTMPSYKCMGZ-UPVQGACJSA-N

物化性质

• 沸点：
  671.2±55.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Val-Asp(OBzl)-OBzl 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  Synthesis and structure-activity relationships of amastatin analogues, inhibitors of aminopeptidase A.

  摘要：

  阿马司他（(2S,3R)-3-氨基-2-羟基-5-甲基己酰基-L-缬氨酰-L-缬氨酰-L-天冬氨酸）的立体异构体和类似物被合成，并测试了它们对氨基肽酶A（AP-A）和其他芳基酰胺酶的抑制活性。在阿马司他中一个新的氨基酸残基的四种立体异构体中，2S立体异构体表现出强烈的活性。在一系列将阿马司他C端氨基酸替换为其他氨基酸的化合物中，含有Asp或Glu的化合物对AP-A显示出最强的活性。在一系列将阿马司他从氨基端开始的第二个或第三个残基替换为其他氨基酸的化合物中，含有疏水氨基酸的化合物表现出强烈的活性。在研究肽链长度与抑制活性关系的研究中，随着肽链长度达到四肽水平，对AP-A的活性逐渐增加。

  DOI：

  10.1271/bbb1961.46.1865
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 、 L-天冬氨酸双苄酯对甲苯磺酸盐 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 Boc-Val-Asp(OBzl)-OBzl
  参考文献：
  名称：

  N-Linked Peptidoresorc[4]arene-Based Receptors as Noncompetitive Inhibitors for α-Chymotrypsin

  摘要：

  This paper deals with the design, synthesis, and evaluation of a new series of receptors for protein surface recognition. The design of these agents is based around the attachment of four constrained dipeptide chains onto a central resorc[4]arene scaffold. By varying the sequence, nature, and stereochemistry of the chains we prepared anionically functionalized N-linked peptidoresorc[4]arenes 12, 13, and 17 by Pd/C-catalyzed hydrogenation of the corresponding benzyl esters 10, 11, and 16, From this family of receptors we have identified noncompetitive inhibitors of alpha-chymotrypsin (ChT), which function by binding to the surface of the enzyme in the neighborhood of the active site cleft (K-i values ranging from 12.4 +/- 5.1 mu M for free carboxylic acid (+)-12b to 0.76 +/- 0.14 mu M for benzyl ester (-)-16a). For anionically functionalized receptors 12, 13, and 17 the ChT inhibition is based essentially on electrostatic interaction, and the bound enzyme can be released from the resorcarene surface by increasing the ionic strength, with its activity almost completely restored. For receptors with terminal benzyl ester groups (10 and 16) a hydrophobic network can be suggested.

  DOI：

  10.1021/jo102592f

文献信息

• Synthesis of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid derivatives. Application to the synthesis of amastatin, an inhibitor of aminopeptidases
  作者：Daniel H. Rich、Byung Jo Moon、Amrit S. Boparai

  DOI：10.1021/jo01300a004

  日期：1980.6
• Synthesis and structure-activity relationships of amastatin analogues, inhibitors of aminopeptidase A.
  作者：Hiroyasu TOBE、Hajime MORISHIMA、Takaaki AOYAGI、Hamao UMEZAWA、Kunio ISHIKI、Kenji NAKAMURA、Takeo YOSHIOKA、Yasutaka SHIMAUCHI、Taiji INUI

  DOI：10.1271/bbb1961.46.1865

  日期：——

  Stereoisomers and analogues of amastatin, [(2S, 3R)-3-amino-2-hydroxy-5-methylhexanoyl]-L-Val-L-Val-L-Asp, were synthesized and their inhibitory activities towards aminopeptidase A (AP-A) and other arylamidases tested. Among the four stereoisomers of a new amino acid residue in amastatin, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the C-terminal amino acid of amastatin was substituted by other amino acids, the one containing Asp or Glu showed the strongest activity towards AP-A. In a series of compounds in which the second or third residue from the amino terminal of amastatin was substituted by other amino acids, the one containing hydrophobic amino acids showed strong activity. In the study of the relationship of the length of the peptide chain and inhibitory activity, the activity towards AP-A was seen to increase until the length of the peptide reached that of a tetrapeptide.

  阿马司他（(2S,3R)-3-氨基-2-羟基-5-甲基己酰基-L-缬氨酰-L-缬氨酰-L-天冬氨酸）的立体异构体和类似物被合成，并测试了它们对氨基肽酶A（AP-A）和其他芳基酰胺酶的抑制活性。在阿马司他中一个新的氨基酸残基的四种立体异构体中，2S立体异构体表现出强烈的活性。在一系列将阿马司他C端氨基酸替换为其他氨基酸的化合物中，含有Asp或Glu的化合物对AP-A显示出最强的活性。在一系列将阿马司他从氨基端开始的第二个或第三个残基替换为其他氨基酸的化合物中，含有疏水氨基酸的化合物表现出强烈的活性。在研究肽链长度与抑制活性关系的研究中，随着肽链长度达到四肽水平，对AP-A的活性逐渐增加。
• <i>N</i>-Linked Peptidoresorc[4]arene-Based Receptors as Noncompetitive Inhibitors for α-Chymotrypsin
  作者：Ilaria D’Acquarica、Antonella Cerreto、Giuliano Delle Monache、Fabiana Subrizi、Alberto Boffi、Andrea Tafi、Stefano Forli、Bruno Botta

  DOI：10.1021/jo102592f

  日期：2011.6.3

  This paper deals with the design, synthesis, and evaluation of a new series of receptors for protein surface recognition. The design of these agents is based around the attachment of four constrained dipeptide chains onto a central resorc[4]arene scaffold. By varying the sequence, nature, and stereochemistry of the chains we prepared anionically functionalized N-linked peptidoresorc[4]arenes 12, 13, and 17 by Pd/C-catalyzed hydrogenation of the corresponding benzyl esters 10, 11, and 16, From this family of receptors we have identified noncompetitive inhibitors of alpha-chymotrypsin (ChT), which function by binding to the surface of the enzyme in the neighborhood of the active site cleft (K-i values ranging from 12.4 +/- 5.1 mu M for free carboxylic acid (+)-12b to 0.76 +/- 0.14 mu M for benzyl ester (-)-16a). For anionically functionalized receptors 12, 13, and 17 the ChT inhibition is based essentially on electrostatic interaction, and the bound enzyme can be released from the resorcarene surface by increasing the ionic strength, with its activity almost completely restored. For receptors with terminal benzyl ester groups (10 and 16) a hydrophobic network can be suggested.