L-Valyl-L-valine benzyl ester | 101222-19-9

• 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: L-Valyl-L-valine benzyl ester
• 英文别名: benzyl (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylbutanoate
• CAS: 101222-19-9
• 化学式: C₁₇H₂₆N₂O₃
• 分子量: 306.405
• InChiKey: AFWAYUZSYOASIP-GJZGRUSLSA-N

物化性质

• 沸点：
  450.9±30.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-Valyl-L-valine benzyl ester 在 钯 氢气 作用下， 以 水 、 溶剂黄146 、 叔丁醇 为溶剂， 生成 缬氨酰-缬氨酸
  参考文献：
  名称：

  N-羧基α-氨基酸酐与α-氨基酸酯逐步反应的位阻

  摘要：

  研究了 4-烷基恶唑烷二酮 (1) (N-羧基 α-氨基酸酐 (NCAs)) 与 α-氨基酸苄酯对甲苯磺酸酯 (2) 在低温和室温下在含三乙胺的乙腈中的反应机理。观察到两种类型的反应：（1）NCAs 的聚合反应是用少量的 2 引发的，产生多肽（6），（2）二肽苄酯（4）是通过 NCAs 与酯类。聚合和二肽形成 (1+2) 似乎都是由酯的氨基对 NCA 的 C-5 碳的亲核攻击引发的。当氨基酸酯 (R2) 的侧链比 NCA (R1) 的侧链更大时，聚合进行。相反，

  DOI：

  10.1246/bcsj.54.2705
• 作为产物：
  描述：

  L-缬氨酸苄酯对甲苯磺酸盐 在 盐酸 作用下， 生成 L-Valyl-L-valine benzyl ester
  参考文献：
  名称：

  Amino acids and peptides. XXX. Synthesis of eglin c(41-49) and eglin c(60-63) and examination of their inhibitory activity towards human leukocyte elastase, cathepsin G, porcine pancreatic elastase and .ALPHA.-chymotrypsin.

  摘要：

  H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OH 和 H-Thr-Asn-Val-Val-OH 分别对应于 eglin c 的序列 41-49 和 60-63，通过采用新开发的 6-氯-2-吡啶酯方法，使用常规溶液法合成。以上两种肽对人类白细胞弹性蛋白酶、半胱天冬酶 G、猪胰弹性蛋白酶和 α-化学蛋白酶的抑制活性进行了比较，分析其与相应甲基酯的活性差异。

  DOI：

  10.1248/cpb.39.184

文献信息

• 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。
• Development of Supramolecular Organo-Gel Based on Tripeptide Skeletons
  作者：Eriko Azuma、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1248/cpb.58.680

  日期：——

  Boc-Ser-Val-Gly-OCH2Ph (31) showed high gelation abilities in the aromatic solvents, particularly in toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized by each molecule of the tripeptide 31. The FT-IR data indicated that formation of antiparallel β-sheets through intermolecular hydrogen bonding was central to the generation of nanofibers during gelation.

  Boc-Ser-Val-Gly-OCH2Ph (31) 在芳香族溶剂中显示出强大的成胶能力，尤其是在甲苯中。31在甲苯中的最低成胶浓度为10 mg/ml，这意味着每分子三肽31固定了2500个甲苯分子。傅里叶变换红外光谱数据显示，通过分子间氢键形成反平行β-折叠是成胶过程中产生纳米纤维的关键。
• Amino Acids and Peptides. XVII. Synthesis of Peptides Related to N-Terminal Portion of Fibrin .ALPHA.-Chain and Their Inhibitory Effect on Fibrinogen/Thrombin Clotting.
  作者：Koichi KAWASAKI、Toshiki TSUJI、Katuhiko HIRASE、Masanori MIYANO、Sachiye INOUE、Masahiro IWAMOTO

  DOI：10.1248/cpb.41.525

  日期：——

  Various peptides related to N-terminal portion of fibrin alpha-chain were synthesized by the solution method and the solid-phase method, and their inhibitory effect on fibrinogen/thrombin clotting was examined. Extension of peptide chain from N-terminal tripeptide decreased the inhibitory effect. The most potent effect was shown by N-terminal decapeptide analog, H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2

  通过溶液法和固相法合成了与纤维蛋白α链的N末端部分有关的各种肽，并研究了它们对纤维蛋白原/凝血酶凝血的抑制作用。N端三肽的肽链延伸降低了抑制作用。N端十肽类似物H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2显示了最有效的作用。
• Intralayer hydrogen-bond-directed self-assembly of nano-fibers from dicarboxylic valylvaline bolaamphiphiles
  作者：Masaki Kogiso、Takeshi Hanada、Kiyoshi Yase、Toshimi Shimizu

  DOI：10.1039/a803606c

  日期：——

  Dicarboxylic L-valyl-L-valine bolaamphiphiles produced nanoscale fibers with widths of 10–30 nm, via proton-triggered self-assembly in water, which are dominated by both intralayer, lateral hydrogen-bond networks between end carboxylic acid groups and parallel β-sheet networks between amide groups.

  二羧酸L-缬氨酰-L-缬氨酸双亲物通过质子触发的水中自组装产生宽度为10-30 nm的纳米级纤维，其主要由末端羧酸基团和平行β之间的层内、横向氢键网络主导-酰胺基团之间的片状网络。
• Jeschkeit,H. et al., Chemische Berichte, 1966, vol. 99, p. 2803 - 2812
  作者：Jeschkeit,H. et al.

  DOI：——

  日期：——