Z-Leu-Leu-OtBu | 40162-58-1

• 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: Z-Leu-Leu-OtBu
• 英文别名: N-benzyloxycarbonyl-L-leucyl-L-leucine t-butyl ester；tert-butyl (2S)-4-methyl-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoate
• CAS: 40162-58-1
• 化学式: C₂₄H₃₈N₂O₅
• 分子量: 434.576
• InChiKey: WFHMUWGAJZNKFD-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Leu-Leu-OtBu 在 palladium on activated charcoal 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 Cbz-Phe-Ser(ψ^Me,Mepro)-Leu-Leu-Ot-Bu
  参考文献：
  名称：

  通过肽键的多个N-甲基化合成IB-01212

  摘要：

  有许多具有多个N-甲基氨基酸的天然肽表现出强大的吸引力生物活性。肽键的N-甲基化也是生物活性肽的药物化学中的标准方法之一，以提高效力和理化性质，特别是膜通透性。在这项研究中，我们研究了在不被甲基化的肽键存在下，通过同时对几个肽键进行N-甲基化来合成N-甲基化肽的简便方法。作为模型研究，我们研究了抗增殖二肽IB-01212的合成。我们使用假脯氨酸在与MeI–Ag 2同时进行N-甲基化的过程中保护非甲基化的肽键O.使用包括二聚/环化过程在内的进一步操作，成功合成了IB-01212及其衍生物。初步的结构-活性关系研究表明，对称结构有助于IB-01212的有效细胞毒活性。

  DOI：

  10.1016/j.bmc.2014.08.036
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 、 L-亮氨酸叔丁酯盐酸盐 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 以93 %的产率得到Z-Leu-Leu-OtBu
  参考文献：
  名称：

  WO2023/195475

  摘要：

  公开号：

文献信息

• Nitrogen-containing 5-membered cyclic compounds and drugs containing these compounds as the active ingredient
  申请人：——

  公开号：US20030153508A1

  公开（公告）日：2003-08-14

  An N-containing five-membered ring compound of formula (I) 1 wherein all symbols are the same as described in the specification, and a non-toxic salt thereof. The compound of formula (I) has an inhibitory activity against cysteine protease and therefore it is useful as an agent for the prophylaxis and/or treatment of inflammatory diseases, diseases induced by apoptosis, diseases induced by disorders of immune responses, autoimmune diseases, diseases induced by decomposition of proteins which compose organism, shock, circulatory system disorders, blood coagulation systems disorders, malignant tumors, acquired immune deficiency syndrome (AIDS) and AIDS-related complex (ARC), parasitic diseases, nerve degeneration diseases, pulmonary disorders, bone resorption diseases, endocrinesthenia, etc.

  式（I）的N-含有五元环化合物，其中所有符号如规范中所述，并且其非毒性盐。式（I）的化合物对半胱氨酸蛋白酶具有抑制活性，因此它可用作预防和/或治疗炎症性疾病、凋亡诱导的疾病、免疫反应紊乱引起的疾病、自身免疫疾病、由组成生物体的蛋白质分解引起的疾病、休克、循环系统紊乱、血液凝血系统紊乱、恶性肿瘤、获得性免疫缺陷综合症（AIDS）和AIDS相关综合症（ARC）、寄生虫病、神经退行性疾病、肺部疾病、骨吸收疾病、内分泌衰弱等方面具有用途。
• N-containing five-membered ring compounds and pharmaceutical agents comprising the same as active ingredient
  申请人：Ohmoto Kazuyuki

  公开号：US20050164954A1

  公开（公告）日：2005-07-28

  An N-containing five-membered ring compound of formula (I) wherein all symbols are the same as described in the specification, and a non-toxic salt thereof. The compound of formula (I) has an inhibitory activity against cysteine protease and therefore it is useful as an agent for the prophylaxis and/or treatment of inflammatory diseases, diseases induced by apoptosis, diseases induced by disorders of immune responses, autoimmune diseases, diseases induced by decomposition of proteins which compose organism, shock, circulatory system disorders, blood coagulation systems disorders, malignant tumors, acquired immune deficiency syndrome (AIDS) and AIDS-related complex (ARC), parasitic diseases, nerve degeneration diseases, pulmonary disorders, bone resorption diseases, endocrinesthenia, etc.

  式(I)表示的含氮五元环化合物，其中所有符号与说明书中描述的相同，并且其非毒性盐。式(I)化合物具有对半胱氨酸蛋白酶的抑制活性，因此可用作预防和/或治疗炎症性疾病、细胞凋亡引起的疾病、免疫反应紊乱引起的疾病、自身免疫性疾病、由组成生物体的蛋白质分解引起的疾病、休克、循环系统紊乱、血液凝固系统紊乱、恶性肿瘤、获得性免疫缺陷综合症（AIDS）和AIDS相关综合症（ARC）、寄生虫病、神经退行性疾病、肺部疾病、骨吸收疾病、内分泌疲劳等药剂。
• NITROGEN-CONTAINING 5-MEMBERED CYCLIC COMPOUNDS AND DRUGS CONTAINING THESE COMPOUNDS AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1254901A1

  公开（公告）日：2002-11-06

  An N-containing five-membered ring compound of formula (I) wherein all symbols are the same as described in the specification, and a non-toxic salt thereof. The compound of formula (I) has an inhibitory activity against cysteine protease and therefore it is useful as an agent for the prophylaxis and/or treatment of inflammatory diseases, diseases induced by apoptosis, diseases induced by disorders of immune responses, autoimmune diseases, diseases induced by decomposition of proteins which compose organism, shock, circulatory system disorders, blood coagulation systems disorders, malignant tumors, acquired immune deficiency syndrome (AIDS) and AIDS-related complex (ARC), parasitic diseases, nerve degeneration diseases, pulmonary disorders, bone resorption diseases, endocrinesthenia, etc.

  式 (I) 的含 N 五元环化合物 其中所有符号与说明书中所述相同，及其无毒盐。 式（I）化合物对半胱氨酸蛋白酶具有抑制活性，因此可用作预防和/或治疗炎症性疾病、由细胞凋亡诱发的疾病、由免疫反应紊乱诱发的疾病、自身免疫性疾病、组成机体的蛋白质分解引起的疾病、休克、循环系统疾病、血液凝固系统疾病、恶性肿瘤、获得性免疫缺陷综合征（AIDS）和 AIDS 相关综合征（ARC）、寄生虫病、神经变性疾病、肺部疾病、骨吸收疾病、内分泌失调等。
• Carbohydrate Protease Conjugates: Stabilized Proteases for Peptide Synthesis
  作者：Charles A. Wartchow、Peng Wang、Mark D. Bednarski、Matthew R. Callstrom

  DOI：10.1021/jo00112a049

  日期：1995.4

  The synthesis of oligopeptides using stable carbohydrate protease conjugates (CPCs) was examined in acetonitrile solvent systems. CPC[alpha-chymotrypsin] was used for the preparation of peptides containing histidine, phenylalanine, tyrosine, and tryptophan in the P-1 position in 60-93% yield. The CPC[alpha-chymotrypsin]-catalyzed synthesis of octamer Z-Gly-Gly-Phe-Gly-Gly-Phe-Gly-Gly-OEt from Z-Gly-Gly-Phe-Gly-Gly-Phe-OMe was achieved in 71% yield demonstrating that synthesis was the dominant kinetic process relative to amide hydrolysis. CPC[papain] was used to synthesize peptides containing both hydrophilic and hydrophobic amino acids. The Pt specificity of papain for aromatic residues was utilized for the 2 + 3 coupling of Z-Tyr-Gly-OMe to H2N-Gly-Phe-Leu-OH to generate the leucine enkephalin derivative in 79% yield. Although papain is nonspecific for the hydrolysis of N-benzyloxycarbonyl amino acid methyl esters in aqueous solution, the rates of synthesis for these derivitives with nucleophile leucine tert-butyl ester differed by nearly 2 orders of magnitude. CPC[thermolysin] was used to prepare the aspartame precursor Z-Asp-Phe-OMe in 90% yield. The increased stability of CPCs prepared from periodate-modified poly(2-methacrylamido-2-deoxy-D-glucose), poly(2-methacrylamido-2-deoxy-D-galactcose) and poly(5-methacrylamido-5-deoxy-D-ribose), carbohydrate materials designed to increase the aldehyde concentration in aqueous solution, suggests that the stability of CPCs is directly related to the aldehyde concentration of the carbohydrate material. Periodate oxidation of poly(2-methacrylamido-2-deoxy-D-glucose) followed by covalent attachment to a-chymotrypsin gave a CPC with catalytic activity in potassium phosphate buffer at 90 degrees C for 2 h.
• Synthesis of a fully protected heptacosapeptide norleucine analog corresponding to positions 21-47 of the primary structure of staphylococcal nuclease
  作者：Allen R. Zeiger、Christian B. Anfinsen

  DOI：10.1021/ja00784a042

  日期：1973.2