N-(N-((苄氧基)羰基)-L-亮氨酰)-L-缬氨酸 | 7801-70-9

• 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
• 中文名称: N-(N-((苄氧基)羰基)-L-亮氨酰)-L-缬氨酸
• 英文名称: Z-Leu-Val
• 英文别名: N-(N-benzyloxycarbonyl-L-leucyl)-L-valine；N-(N-Benzyloxycarbonyl-L-leucyl)-L-valin；Z-Leu-val-OH；(2S)-3-methyl-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]butanoic acid
• CAS: 7801-70-9
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: MUJSLBXYEJRINU-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N-((苄氧基)羰基)-L-亮氨酰)-L-缬氨酸 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.75h， 生成
  参考文献：
  名称：

  Inhibition studies of some serine and thiol proteinases by new leupeptin analogs

  摘要：

  Fifteen tripeptide analogues of leupeptin containing either a C-terminal argininal or lysinal were synthesized. The synthetic analogues were tested, using spectrophotometric assay techniques, as inhibitors of trypsin, kallikrein, thrombin, plasmin, and cathepsin B. The lysinal analogues were fairly selective as inhibitors of cathepsin B activity, Acetyl-L-leucyl-L-valyl-L-lysinal (21) showed a stronger inhibition of cathepsin B (IC50 = 4 nanomolar) than leupeptin. Acetyl-L-phenylalanyl-L-valyl-L-argininal (2i) was found to be a good inhibitor of cathepsin B (IC50 = 0.039 muM), thrombin (IC50 = 1.8 muM), and plasmin (IC50 = 2.2 muM).

  DOI：

  10.1021/jm00060a016
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 在 四氢呋喃 、 氯甲酸乙酯 、 三乙胺 作用下， 生成 N-(N-((苄氧基)羰基)-L-亮氨酰)-L-缬氨酸
  参考文献：
  名称：

  The Synthesis of L-Seryl-L-histidyl-L-leucyl-L-valyl- L-glutamic Acid, a Peptide with Strepogenin Activity

  摘要：

  DOI：

  10.1021/ja01599a032

文献信息

• Succinimidyl Carbamate Derivatives fromN-Protected α-Amino Acids and Dipeptides―Synthesis of Ureidopeptides and Oligourea/Peptide Hybrids
  作者：Lucile Fischer、Vincent Semetey、Jose-Manuel Lozano、Arnaud-Pierre Schaffner、Jean-Paul Briand、Claude Didierjean、Gilles Guichard

  DOI：10.1002/ejoc.200601010

  日期：2007.5

  direct precursors of 1,3,5-triazepan-2,6-diones, a novel class of conformationally constrained dipeptide mimetics. Herein, we have evaluated the use of these building blocks for the synthesis of ureido-peptides (in solution and on solid support), peptidyl hydantoins, oligoureas and some oligo(urea/amide) hybrids. Conformational investigations by NMR of ureidotripeptide 6i and pentamer 10, consisting of alternating

  由多种N制备琥珀酰亚胺（1-[（烷氧基）羰基]氨基}-1-X-甲基）氨基甲酸酯（4）和琥珀酰亚胺[1-（酰氨基）-1-X-甲基]氨基甲酸酯（5）描述了 -Boc-、-Z- 或 -Fmoc 保护的 α-氨基酸和二肽以及氨基甲酸酯的结构特征。我们之前已经表明，源自 N-Boc 二肽的琥珀酰亚胺氨基甲酸酯 5 可以作为 1,3,5-三氮杂-2,6-二酮（一类新型的构象受限二肽模拟物）的直接前体。在此，我们评估了这些构件在合成脲基肽（在溶液中和在固体支持物上）、肽基乙内酰脲、低聚脲和一些低聚（脲/酰胺）杂化物的用途。脲基三肽 6i 和五聚体 10 的 NMR 构象研究，由交替的酰胺和脲组成，建议折叠构象（即尿素转向）以尿素键的顺，反（E，Z）几何形状为特征，填充在 [D5] 吡啶和 [D6] DMSO 溶液中。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
• New leupeptin analogs: synthesis and inhibition data
  作者：Rose M. McConnell、George E. Barnes、Charles F. Hoyng、J. Martin Gunn

  DOI：10.1021/jm00163a014

  日期：1990.1

  and plasmin activity. Of the three enzymes tested, (benzyloxycarbonyl)-L-leucyl-L-leucyl-L-ornithinal (2i) showed significant inhibition of kallikrein activity only. Modifications made in the composition and sequence of the P2 and P3 amino acids also resulted in variations in the inhibitory activity of the analogues. In general, plasmin showed a strong preference for inhibitors which contain an L-phenylalanyl-L-leucyl

  介绍了几种含有C末端精氨酸，赖氨酸或鸟氨酸单位的亮肽素的三肽类似物的合成。测试了合成类似物作为胰蛋白酶，纤溶酶和激肽释放酶的抑制剂。（苯甲氧基羰基）-L-亮氨酰-L-亮氨酰-L-精氨酸（2a）作为胰蛋白酶和纤溶酶活性的抑制剂的功效明显低于Leupeptin。（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-赖氨酸（2e）和（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-鸟氨酸（2i）显示出与（苄氧羰基）-L-亮氨酰-L不同的抑制特性。 L-亮氨酰-L-精氨酸（2a）。尽管（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-精氨酸（2a）对所有三种酶均显示中等抑制作用，但（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-赖氨酸（2e）效果不佳胰蛋白酶和纤溶酶活性的抑制剂。在测试的三种酶中，（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-鸟氨酸（2i）仅显示出激肽释放酶活性的显着抑制。对P2和P3氨基酸的组成和序列进行的修饰也导致
• Studies on Serine Peptides. IV. Synthesis of L-Seryl-L-histidyl-L-leucyl-L-valyl-L-glutamic Acid with Strepogenin Activity.
  作者：Kenji Okawa

  DOI：10.1246/bcsj.31.88

  日期：1958.1

  L-Seryl-L-histidyl-L-leucyl-L-valyl-L-glutamic acid having strepogenin activity has been synthesized from O-Bz-L-serine as a starting material in a good yield by Sheehan’s dicyclohexylcarbodiimide ...

  以 O-Bz-L-丝氨酸为起始原料，Sheehan 的二环己基碳化二亚胺以良好的收率合成了具有链生成素活性的 L-Seryl-L-histidyl-L-leucyl-L-valyl-L-谷氨酸...
• Design, Synthesis, and Biological Evaluation of Peptidomimetic Inhibitors of Factor XIa as Novel Anticoagulants
  作者：Jian Lin、Hongfeng Deng、Lei Jin、Pramod Pandey、Jesse Quinn、Susan Cantin、Michael J. Rynkiewicz、Joan C. Gorga、Frank Bibbins、Cassandra A. Celatka、Pamela Nagafuji、Thomas D. Bannister、Harold V. Meyers、Robert E. Babine、Neil J. Hayward、David Weaver、Howard Benjamin、Frans Stassen、Sherin S. Abdel-Meguid、James E. Strickler

  DOI：10.1021/jm060978s

  日期：2006.12.1

  Human coagulation factor XIa (FXIa), a serine protease activated by site-specific cleavage of factor XI by thrombin, FXIIa, or autoactivation, is a critical enzyme in the amplification phase of the coagulation cascade. To investigate the potential of FXIa inhibitors as safe anticoagulants, a series of potent, selective peptidomimetic inhibitors of FXIa were designed and synthesized. Some of these inhibitors

  人凝血因子XIa（FXIa）是一种通过凝血酶，FXIIa或自发激活因子XI进行位点特异性切割而激活的丝氨酸蛋白酶，是凝血级联反应扩增阶段的关键酶。为了研究FXIa抑制剂作为安全抗凝剂的潜力，设计并合成了一系列有效的，选择性的FXIa拟肽抑制剂。这些抑制剂中的一些表现出低的纳摩尔FXIa抑制活性，FXa选择性> 1000倍，凝血酶选择性> 100倍。这些抑制剂之一的X射线结构36显示了其与FXIa的独特结合相互作用。化合物32在人血浆中以2.4 microM引起的活化部分凝血活酶时间的增加了一倍，并且在静脉血栓形成的大鼠模型中有效。
• Substituted 5-amino-4-hydroxyvaleryl derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04613676A1

  公开（公告）日：1986-09-23

  Compounds of the formula ##STR1## in which R.sub.1 represents hydrogen or acyl, X.sub.1 represents an optionally N-alkylated amino acid residue that is bonded N-terminally to R.sub.1 and C-terminally to X.sub.2, X.sub.2 represents an optionally N-alkylated amino acid residue that is bonded N-terminally to X.sub.1 and C-terminally to the group --NR.sub.2 --, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents hydrogen, alkyl, cycloalkyl, aryl- lower alkyl or aryl, R.sub.4 represents hydroxy or etherified or esterified hydroxy, R.sub.5 represents alkyl, cycloalkyl, aryl-lower alkyl or aryl, and R.sub.6 represents free or substituted amino or substituted hydroxy, and salts of such compounds having salt-forming groups inhibit the blood pressure-increasing action of the enzyme renin and can be used as anti-hypertensives.

  式子为##STR1##的化合物，其中R.sub.1代表氢或酰基，X.sub.1代表可选的N-烷基化氨基酸残基，该残基与R.sub.1在N-末端连接，在C-末端连接X.sub.2，X.sub.2代表可选的N-烷基化氨基酸残基，该残基与X.sub.1在N-末端连接，在C-末端连接--NR.sub.2--基团，R.sub.2代表氢或低碳基，R.sub.3代表氢、烷基、环烷基、芳基-低碳基或芳基，R.sub.4代表羟基或醚化或酯化羟基，R.sub.5代表烷基、环烷基、芳基-低碳基或芳基，R.sub.6代表自由或取代氨基或取代羟基，以及具有形成盐的基团的这些化合物的盐，可以抑制酶肾素的升高血压作用，并可用作抗高血压药。