tert-butyl ((S)-1-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate | 74257-73-1

• 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: tert-butyl ((S)-1-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• 英文别名: N-(tert-Butoxycarbonyl)-L-phenylalanyl-L-leucinamide；tert-butyl N-[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 74257-73-1
• 化学式: C₂₀H₃₁N₃O₄
• 分子量: 377.484
• InChiKey: RAFQNNBXUDRUGK-HOTGVXAUSA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  618.8±55.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl ((S)-1-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 L-Phe-L-Leu-NH2
  参考文献：
  名称：

  用新的二肽基腈抑制剂作为锥虫杀虫剂定位半胱氨酸蛋白酶的S1和S1'亚位点。

  摘要：

  半胱氨酸蛋白酶Cruzipain被认为是治疗南美锥虫病的有效治疗靶标。设计，合成了一系列26种新化合物，并针对重组Cruzain（Cz）进行了测试，以绘制其S1 / S1´子位图。在一组四个人类半胱氨酸蛋白酶（CatB，CatK，CatL，CatS）和墨西哥利什曼原虫CPB（一组可能是治疗皮肤利什曼病的潜在靶标）上对同一系列进行了评估。合成的化合物是基于P1（十个），P2（六个）和P3（四个不同的结构单元）中不同部分最有希望的组合而设计的二肽基腈。八个化合物的Cz的Ki小于20.0 nM，而三个化合物的LmCPB符合这些标准。三种抑制剂的EC50值为ca。4.0微米 因此，根据其抗胰锥作用，与苯硝唑相当。我们的作图方法和各自的结构活性关系为治疗相关的半胱氨酸蛋白酶的特定配体-靶标相互作用提供了见识。

  DOI：

  10.1371/journal.pntd.0007755
• 作为产物：
  描述：

  alpha-叔丁氧羰基-L-苯丙氨酰-L-亮氨酸 在 1-hydroxy-1H-benzotriazole ammonium salt 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到tert-butyl ((S)-1-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis and biological activity of branched enkephalin analogues

  摘要：

  The synthesis and biological activity of a new type of enkephalin analogs are reported. A series of branched penta peptides of the enkephalin sequence with replacement of 2-glycine by D-ornithine and branching of the peptide chain in position 2 by attachment of proline, leucine, asparagine or methionine residues to the delta-amino group of D-ornithine were synthesized by classical solution methodology. Analgesic activity of the new analogs was assayed by the 'tail pinch' method following intracisternal and intravenous administrations to mice. They showed higher analgesic potency and longer duration of action as compared to linear and cyclic pentapeptides with the same amino acid composition. The activity determined in the GPI and MVD bioassays, and in a binding assay, revealed the preference of the branched analogs for the mu-type of opioid receptor over the delta-type. These results raise the possibility to synthesize enkephalin analogs with high analgesic potency and opiate receptor selectivity by varying the chemical character and length of the side chain in the 2-position. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80060-3

文献信息

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING PROTEIN EMBRYONIC ECTODERM DEVELOPMENT ACTIVITY AND TREATING DISEASE<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR L'INHIBITION DE L'ACTIVITÉ DE DÉVELOPPEMENT D'ECTODERME EMBRYONNAIRE DE PROTÉINE ET DE TRAITEMENT D'UNE MALADIE
  申请人：EXO THERAPEUTICS INC

  公开号：WO2021195183A1

  公开（公告）日：2021-09-30

  The invention provides compounds that are inhibitors of the protein embryonic ectoderm development (EED), pharmaceutical compositions, their use in modulating the activity of EED, and their use in the treatment of medical disorders, such as cancer. The invention further provides methods of treating medical disorders, such as cancer, and covalently modifying and/or modulating the activity of EED, using an agent that reacts with, and forms a covalent bond to, cysteine324 of EED.

  这项发明提供了抑制蛋白胚胎外胚层发育（EED）的化合物，药物组合物，它们在调节EED活性中的应用，以及它们在治疗癌症等医学疾病中的应用。该发明还提供了治疗医学疾病（如癌症）的方法，并利用一种与EED的半胱氨酸324发生反应并形成共价键的试剂，对EED进行共价修饰和/或调节活性。
• Bicyclic turned dipeptide (BTD) as a β-turn mimetic; its design, synthesis and incorporation into bioactive peptides
  作者：Ukon Nagai、Kazuki Sato、Rika Nakamura、Rika Kato

  DOI：10.1016/s0040-4020(01)90216-9

  日期：1993.3

  After reviewing the development of β-turn mimetics briefly, design, synthesis and incorporation into bioactive peptides of BTD will be mentioned. The biological activity of the BTD containing peptides and synthesis of some BTD derivatives will also be described.

  在简要回顾了β-turn模拟物的发展之后，将提及BTD的设计，合成和并入BTD的生物活性肽。还将描述含BTD的肽的生物活性以及一些BTD衍生物的合成。
• [EN] A PHOTOLABILE LINKER FOR THE SOLID-PHASE SYNTHESIS OF HYDRAZIDES AND PYRANOPYRAZOLES<br/>[FR] LIEUR PHOTOLABILE POUR LA SYNTHÈSE EN PHASE SOLIDE D'HYDRAZIDES ET DE PYRANOPYRAZOLES
  申请人：UNIV DANMARKS TEKNISKE

  公开号：WO2015036481A1

  公开（公告）日：2015-03-19

  The photolabile hydrazine linker of the present invention is based on the o-nitro-veratryl group, which is capable of releasing hydrazide derivatives upon UV irradiation. The linker allows for a new solid-phase peptide synthesis (SPPS) strategy which is fully orthogonal to the most commonly used protecting groups and chemical methods in SPPS and shows excellent compatibility with peptide composition, notably the 20 naturally occurring α-amino acid residues (even in their side-chain protected form) are accepted in the C-terminal of the peptide hydrazides. Furthermore, the linker unit can be applied to synthesize combinatorial libraries of biological interesting heterocyclic compounds, such as pyranopyrazoles.

  本发明的光敏式肼连接剂基于邻硝基维拉特基团，能够在紫外辐射下释放肼衍生物。该连接剂允许一种全新的固相肽合成（SPPS）策略，与SPPS中最常用的保护基和化学方法完全正交，并且与肽组成非常兼容，特别是在肽肼酰的C末端接受20种天然存在的α-氨基酸残基（即使是它们的侧链保护形式）。此外，该连接单元可用于合成生物感兴趣的杂环化合物的组合式库，如吡喃吡唑。
• Synthetic inhibitors of mammalian collagenase
  申请人：Research Corporation Technologies, Inc.

  公开号：US05686422A1

  公开（公告）日：1997-11-11

  The present invention relates to compounds of the formula: R.sub.1 SCH(R.sub.2)CH(R.sub.3)CO-AA.sub.1 \x9bAA.sub.2 !.sub.m \x9bAA.sub.3 !.sub.n --X or HSCH.sub.2 \x9bCH.sub.2 CH(CH.sub.3).sub.2 !CO--Nal--NH.sub.2 wherein Nal is L-3-(2-naphthyl)alanine; m is the integer 0 or 1; n is an integer from 0-2; AA.sub.1 is a non-polar hydrophobic aromatic amino acid; AA.sub.2 is alanine, glycine, leucine, isoleucine or phenylalanine; AA.sub.3 is one of the twenty naturally occurring amino acids, preferably glutamine or arginine; R.sub.1 is hydrogen, alkyl having from 1-10 carbon atoms, alkanoyl having from 2-10 carbon atoms, or aroyl having from 7-10 carbon atoms; R.sub.2 is hydrogen or alkyl having from 1-6 carbon atoms; R.sub.3 is hydrogen, alkyl having from 2-10 carbon atoms, cycloalkyl having from 3-6 carbon atoms, aryl or arylalkyl, wherein aryl moieties have from 6-10 carbon atoms; X is NH.sub.2, OH, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and salts thereof.

  本发明涉及以下结构的化合物：R.sub.1 SCH(R.sub.2)CH(R.sub.3)CO-AA.sub.1 \x9bAA.sub.2 !.sub.m \x9bAA.sub.3 !.sub.n --X 或 HSCH.sub.2 \x9bCH.sub.2 CH(CH.sub.3).sub.2 !CO--Nal--NH.sub.2，其中Nal是L-3-(2-萘基)丙氨酸；m为整数0或1；n为0-2的整数；AA.sub.1为非极性疏水芳香族氨基酸；AA.sub.2为丙氨酸、甘氨酸、亮氨酸、异亮氨酸或苯丙氨酸；AA.sub.3为二十种天然存在的氨基酸之一，最好为谷氨酰胺或精氨酸；R.sub.1为氢、具有1-10个碳原子的烷基、具有2-10个碳原子的烷酰基或具有7-10个碳原子的芳酰基；R.sub.2为氢或具有1-6个碳原子的烷基；R.sub.3为氢、具有2-10个碳原子的烷基、具有3-6个碳原子的环烷基、芳基或芳基烷基，其中芳基部分具有6-10个碳原子；X为NH.sub.2、OH、OCH.sub.3或OCH.sub.2 CH.sub.3；及其盐。
• Environmentally Conscious In-Water Peptide Synthesis Using Boc Strategy
  作者：Keiko Hojo、Suzuko Fujiwara、Hoshito Inai、Yuki Manabe、Yuko Tsuda

  DOI：10.1007/s10989-021-10354-1

  日期：2022.3

  environmentally balanced method of peptide synthesis, we are focusing on developing organic solvent-free synthetic methods using water, an environmentally friendly solvent. In current peptide synthesis, the most common building blocks are Boc- and Fmoc-protected amino acids, which are highly soluble in organic solvents. We previously reported a technique for solid-phase peptide synthesis in water that utilizes

  寻求一种更环保的多肽合成方法，我们专注于开发使用水这一环保溶剂的无有机溶剂合成方法。在目前的肽合成中，最常见的结构单元是 Boc 和 Fmoc 保护的氨基酸，它们高度溶于有机溶剂。我们之前报道了一种在水中进行固相肽合成的技术，该技术利用转化为水分散性纳米颗粒的 Fmoc-氨基酸。众所周知，Boc 策略适用于工业化学和绿色化学，因为在 Boc 基团的脱保护步骤中仅产生气体而没有任何其他副产物。在这里，我们总结了基于纳米级反应物的 MW 辅助偶联反应的使用 Boc-氨基酸的水中液相和固相方法，