N-benzyloxycarbonyl-L-valyl-L-phenylalaninol | 148743-43-5

• 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-benzyloxycarbonyl-L-valyl-L-phenylalaninol
• 英文别名: benzyl N-[(2S)-1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 148743-43-5
• 化学式: C₂₂H₂₈N₂O₄
• 分子量: 384.475
• InChiKey: VLFHBNSJHLMKMM-PMACEKPBSA-N

物化性质

• 熔点：
  151-153 °C
• 沸点：
  634.7±55.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-valyl-L-phenylalaninol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (S)-2-amino-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-3-methylbutanamide
  参考文献：
  名称：

  化学选择性催化共轭胺上的醇加成。

  摘要：

  描述了在胺存在下醇的高度化学选择性共轭加成。催化剂的协同性质使醇对胺的化学选择性活化成为可能，使共轭物加成到柔软的路易斯碱性α，β-不饱和腈中。腈官能度的发散转化突出了本催化的实用性。

  DOI：

  10.1002/anie.201309755
• 作为产物：
  描述：

  CBZ-L-缬氨酸 、 L-苯丙氨醇 在 N-甲基吗啉 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 N-benzyloxycarbonyl-L-valyl-L-phenylalaninol
  参考文献：
  名称：

  CuI催化的含膦基-恶唑啉配体的（E）-硝基烯烃和环烯酮的对映体选择性1,4-烷基

  摘要：

  已开发出新的膦基-恶唑啉配体，该配体已被用于铜催化的（E）-硝基烯烃的铜对映体选择性共轭加成反应。

  DOI：

  10.1002/ejoc.201800476

文献信息

• Inhibitors of Tripeptidyl Peptidase II. 2. Generation of the First Novel Lead Inhibitor of Cholecystokinin-8-Inactivating Peptidase:  A Strategy for the Design of Peptidase Inhibitors
  作者：C. Robin Ganellin、Paul B. Bishop、Ramesh B. Bambal、Suzanne M. T. Chan、James K. Law、Benoit Marabout、Pratibha Mehta Luthra、Andrew N. J. Moore、Olivier Peschard、Pierre Bourgeat、Christiane Rose、Froylan Vargas、Jean-Charles Schwartz

  DOI：10.1021/jm990226g

  日期：2000.2.1

  fluorimetric assay based on the hydrolysis of the artificial substrate Ala-Ala-Phe-amidomethylcoumarin. A series of di- and tripeptides having various alkyl or aryl side chains was studied to determine the accessible volume for binding and to probe the potential for hydrophobic interactions. From this initial study the tripeptides Ile-Pro-Ile-OH (K(i) = 1 microM) and Ala-Pro-Ala-OH (K(i) = 3 microM) and dipeptide

  失活胆囊收缩素8（CCK-8）的肽酶是一种丝氨酸肽酶，已证明是三肽基肽酶II的膜结合同工型（EC 3.4.14.10）。它在Met-Gly键处裂解神经递质CCK-8硫酸盐，得到Asp-Tyr（SO（3）H）-Met-OH + Gly-Trp-Met-Asp-Phe-NH（2）。为了寻找该肽酶的可逆抑制剂，使用基于人工底物Ala-Ala-Phe-酰胺基甲基香豆素水解的荧光分析法来表征酶促结合亚位点。对具有各种烷基或芳基侧链的一系列二肽和三肽进行了研究，以确定可结合的体积并探讨疏水相互作用的可能性。根据这项初步研究，三肽Ile-Pro-Ile-OH（K（i）= 1 microM）和Ala-Pro-Ala-OH（K（i）= 3 microM）和二肽酰胺Val-Nvl-NHBu（K（ i）= 3 microM）作为线索出现。这些结构的比较导致Val-Pro-NHBu（K（i）= 0.57 micr
• PROCESS FOR PRODUCING PEPTIDYL ALDEHYDES
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：EP1123919A1

  公开（公告）日：2001-08-16

  The present invention provides a method of producing a peptidyl aldehyde derivative of the formula (II) wherein A is acyl derived from amino acid, and R1 and R2 are different and one is hydrogen atom and the other is optionally substituted lower alkyl, which includes oxidizing a peptidyl alcohol derivative of the formula (I) wherein each symbol is as defined above, with DMSO in the presence of diisopropylethylamine. According to the present invention, formation of a stereoisomer can be prevented or suppressed.

  本发明提供了一种制备肽醛衍生物的方法，其化学式为(II)，其中A是来自氨基酸的酰基，R1和R2不同，其中一个是氢原子，另一个是可选取代的较低烷基。该方法包括在二异丙基乙基胺的存在下，使用DMSO氧化化学式为(I)的肽醇衍生物，其中每个符号如上所定义。根据本发明，可以防止或抑制立体异构体的形成。
• Inhibitors of HIV-1 Proteinase Containing 2-Heterosubstituted 4-Amino-3-hydroxy-5-phenylpentanoic Acid: Synthesis, Enzyme Inhibition, and Antiviral Activity
  作者：Dieter Scholz、Andreas Billich、Brigitte Charpiot、Peter Ettmayer、Philipp Lehr、Brigitte Rosenwirth、Erwin Schreiner、Hubert Gstach

  DOI：10.1021/jm00045a013

  日期：1994.9

  A convenient procedure for the synthesis of 2-heterosubstituted statine derivatives as novel building blocks in HN-protease inhibitors has been developed. The synthesis starts with protected L-phenylalaninols, which were converted to gamma-amino alpha,beta-unsaturated esters in a one-pot procedure. A highly diastereoseletive epoxidation of the N-protected (E)-enoates, followed by regioselective ring opening of the corresponding 2,3-epoxy esters with a variety of heteronucleophiles, resulted in 2-heterosubstituted statine derivatives. The overall stereochemical outcome of the transformations meets the required configuration of HIV-protease inhibitors. The short, synthetically flexible, and highly diastereoselective synthesis of 2-heterosubstituted statines has enabled a broad derivation, covering the S3, S2, and S1'-S3' sites of the enzyme. In a series of 46 derivatives, several potent inhibitors were obtained with K-i values as low as 3.4 nM and antiviral activity in the lower nanomolar-range. The structural parameters of the compounds which determine the potency of inhibition and selectivity for the viral enzyme are discussed.
• Formation of Urea Dipeptides from Carbonyldiimidazole:  Application toward the Protease Inhibitors GE 20372 and MAPI
  作者：Xiaowei Zhang、Jason Rodrigues、Lawrence Evans、Becky Hinkle、Lisa Ballantyne、Michael Peña

  DOI：10.1021/jo970514p

  日期：1997.9.1
• Kammermeier, Bernhard; Beck, Gerhard; Holla, Wolfgang, Chemistry - A European Journal, 1996, vol. 2, # 3, p. 307 - 315
  作者：Kammermeier, Bernhard、Beck, Gerhard、Holla, Wolfgang、Jacobi, Detlev、Napierski, Bernd、Jendralla, Heiner

  DOI：——

  日期：——