Z-Leu-NH-Bzl | 28117-45-5

• 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: Z-Leu-NH-Bzl
• 英文别名: N-Benzyloxycarbonyl-L-leucin-benzylamid；benzyl N-[(2S)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 28117-45-5
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: VZKZVLMPJAVFDP-IBGZPJMESA-N

物化性质

• 熔点：
  110 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  572.7±50.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-Leu-NH-Bzl 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 H-Val-Ser-Leu-NH-Bzl
  参考文献：
  名称：

  Arecoline Tripeptide Inhibitors of Proteasome

  摘要：

  The 26S proteasome is a multicatalytic protease complex that plays an essential role in intracellular protein degradation. We have synthesized and tested a series of arecoline peptide derivatives where the peptide portion derives from a screening of tripeptide sequences, and the arecoline moiety has been considered as a potential substrate for catalytic threonine. Derivatives 17-19 are the best compounds of the series, showing chymotryptic-like ( 5) inhibition (IC50 congruent to 1 muM) and favorable pharmacokinetic properties.

  DOI：

  10.1021/jm0309102
• 作为产物：
  描述：

  L-亮氨酸,N-(1,3-二羰基丁基)- 在 羟胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 Z-Leu-NH-Bzl
  参考文献：
  名称：

  .beta.-Carbonylamides in peptide chemistry. Synthesis of optically active peptides from N-acetoacetylamino acids via 2-acetonylideneoxazolidin-5-ones

  摘要：

  DOI：

  10.1021/jo00812a021

文献信息

• Amidation of unactivated ester derivatives mediated by trifluoroethanol
  作者：Christopher G. McPherson、Nicola Caldwell、Craig Jamieson、Iain Simpson、Allan J. B. Watson

  DOI：10.1039/c7ob00593h

  日期：——

  A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity

  已经开发了由2,2,2-三氟乙醇介导的催化酰胺化方案，可促进未活化的酯和胺的缩合，同时提供仲酰胺和叔酰胺。描述了该方法的完整范围和局限性，以及具有挑战性的底物（如无环仲胺和手性酯）的修饰条件，并保留了手性完整性。
• Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands
  作者：Jorge Escorihuela、M. Isabel Burguete、Gregori Ujaque、Agustí Lledós、Santiago V. Luis

  DOI：10.1039/c6ob01878e

  日期：——

  The enantioselective alkylation of aldehydes catalysed by nickel(II)-complexes derived from α-amino amides was studied by means of density functional theory (DFT) and ONIOM (B3LYP:UFF) calculations. A mechanism was proposed in order to investigate the origin of enantioselectivity. The chirality-determining step for the alkylation was the formation of the intermediate complexes with the involvement

  通过密度泛函理论（DFT）和ONIOM（B3LYP：UFF）计算研究了由α-氨基酰胺衍生的镍（II）配合物催化的醛的对映选择性烷基化。为了研究对映选择性的起源，提出了一种机制。烷基化的手性确定步骤是中间体配合物的形成，其中涉及5/4 / 4-稠合的三环过渡态。理论上预测的主要产物为（S）-构型，与实验观察结果非常吻合。检查了反应范围，观察到对映选择性添加Et 2 Zn和Me 2的高产率和对映选择性锌为芳香族和脂肪族醛。
• Amino-acids and peptides. Part XXVII. Further studies on esters of 1-hydroxypiperidine
  作者：J. H. Jones、G. T. Young

  DOI：10.1039/j39680000053

  日期：——

  Acylamino-acid 1-piperidyl esters have been obtained in a high state of purity by the use of ‘Reagent K’[3-(2-ethyl-5-isoxazolio)benzenesulphonate], and new esters prepared by this and by previously known methods are reported. Standard recemisation tests showed that the new procedure gave an optically pure ester from benzyloxycarbonylglycyl-L-phenylalanine, but some racemate was formed from benzoyl-L-leucine

  通过使用“试剂K” [3-（2-乙基-5-异恶唑啉基）苯磺酸酯]，可以得到高纯度的酰基氨基酸1-哌啶基酯，以及由此和通过已知方法制备的新酯被报道。标准的重新证明测试表明，新方法从苄氧羰基甘氨酰-L-苯丙氨酸得到了光学纯的酯，但是由苯甲酰基-L-亮氨酸形成了一些外消旋物。报道了1-哌啶基酯的其他反应。苄氧羰基-L缩合反应中乙酸与胺的最佳摩尔比已经发现氯仿中的亮氨酸1-哌啶基酯与甘氨酸乙酯在1至2之间。1,2,4-三唑催化该反应（以二甲基甲酰胺为溶剂），也可催化酯与苄胺的反应，但乙酸更有效。描述了1-哌啶碳酸叔丁酯的制备及其在形成叔丁氧羰基甘氨酸中的用途。与L-赖氨酸，碳酸苄基1-哌啶酯以58％的收率得到α-苄氧基羰基-L-赖氨酸。据报道，甘氨酸乙酯在乙酸存在下裂解邻苯二甲酰亚胺基酯的邻苯二甲酰亚胺基。
• Amino acid derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0386611A3

  公开（公告）日：1992-04-15

  Compounds of the formula wherein R¹ represents alkoxycarbonyl, aralkoxycarbonyl, alkanoyl, aralkanoyl, aroyl, cycloalkylcarbonyl, heterocyclylcarbonyl, heterocyclyl-alkanoyl, 6-(dibenzylcarbamoyl)-4-oxohexanoyl or an acyl group of an α-amino acid in which the amino group is substituted by alkoxycaronyl, aralkoxycarbonyl, diaralkylcarbamoyl, diaralkylalkanoyl or aralkanoyl; R² represents alkyl, cycloalkylalkyl or aralkyl; R³ represents hydrogen or alkyl; R⁴ represents alkyl; and one of R⁵ and R⁶ represents hydrogen and the other represents hydrogen, alkyl, aryl, aralkyl, 1-alkoxycarbonyl-2-phenylethyl, 1-alkoxycarbonyl-2-(imidazol-4-yl)ethyl, 2-(imidazol-1-yl)ethyl, indanyl, heterocyclyl-alkyl, carboxyalkyl, alkoxycarbonylalkyl, aryloxycarbonylalkyl, aralkoxycarbonylalkyl or a group of the formula -A-N(Ra)(Rb) in which A represents alkylene and Ra and Rb each represent alkyl or Ra and Rb together represent a pentamethylene group in which one methylene group can be replaced by NH, N-alkyl, N-alkanoyl, N-aralkoxy carbonyl, O, S, SO or SO₂; or R⁵ and R⁶ together with the nitrogen atom to which they are attached represent a 1,2,3,4-tetrahydroisoquinoline ring; one of W and X represents hydrogen and the other represents hydroxy or amino or W and X together represent hydroxyimino and Y represents hydrogen or, where one of W and X represents hydrogen and the other represents hydroxy, Y can also represent hydroxy, and pharmaceutically acceptable acid addition salts thereof can be used as medicaments for the treatment and prophylaxis of viral infections, particularly of infections caused by HIV and other retroid viruses. They can be manufactured according to generally known procedures.

  该公式化合物中，其中R¹代表烷氧羰基、芳基烷氧羰基、烷酰基、芳基烷酰基、芳酰基、环烷基羰基、杂环烷基羰基、杂环烷基-烷酰基、6-(二苯甲基羰基)-4-氧代己酰基或α-氨基酸的酰基，其中氨基团被烷氧羰基、芳基烷氧羰基、二芳基甲基羰基、二芳基烷酰基或芳基取代；R²代表烷基、环烷基烷基或芳基烷基；R³代表氢或烷基；R⁴代表烷基；而R⁵和R⁶中的一个代表氢，另一个代表氢、烷基、芳基、芳基烷基、1-烷氧羰基-2-苯乙基、1-烷氧羰基-2-(咪唑-4-基)乙基、2-(咪唑-1-基)乙基、茚基、杂环烷基-烷基、羧基烷基、烷氧羰基烷基、芳氧羰基烷基、芳基烷氧羰基烷基或-A-N(Ra)(Rb)的基团，其中A代表烷基，Ra和Rb各自代表烷基，或Ra和Rb一起代表一个五甲烷基基团，其中一个亚甲基可以被NH、N-烷基、N-烷酰基、N-芳氧羰基、O、S、SO或SO₂取代；或者R⁵和R⁶与它们连接的氮原子一起代表1,2,3,4-四氢异喹啉环；W和X中的一个代表氢，另一个代表羟基或氨基，或者W和X一起代表羟亚胺基，Y代表氢或者其中一个代表氢，另一个代表羟的情况下，Y也可以代表羟，其药学上可接受的酸盐可用作治疗和预防病毒感染的药物，特别是HIV和其他逆转录病毒引起的感染。它们可以按照通常已知的程序制造。
• Schwyzer; Iselin, Annales Academiae Scientiarum Fennicae, Series A2: Chemica, 1955, # 60, p. 181,188
  作者：Schwyzer、Iselin

  DOI：——

  日期：——