Boc-Val-Val-Val | 108334-67-4

• 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: Boc-Val-Val-Val
• 英文别名: N-Boc-Val-Val-Val-OH；Boc-(L-Val)3-OH；Boc-Val-Val-Val-OH；(2S)-3-methyl-2-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]butanoyl]amino]butanoic acid
• CAS: 108334-67-4
• 化学式: C₂₀H₃₇N₃O₆
• 分子量: 415.53
• InChiKey: CBFRVMIYOXDVQI-KKUMJFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Val-Val-Val 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  使用碳环 α,α-二取代 α-氨基酸在 α-螺旋钉合肽中进行 E-选择性闭环复分解

  摘要：

  我们在位置i和i + 4 的 α-螺旋钉合肽中提出了E选择性闭环复分解反应。使用两个手性碳环 α,α-二取代 α-氨基酸 (1 S ,3 S )-Ac 5 c 3OAll和 (1 R ,3 S )-Ac 5 c 3OAll提供了 ≤59:1 E : Z比率的高E选择性，而E : Z比率为 2.1–0.5:1 的混合物是用标准无环 ( S )-(4-戊烯基)丙氨酸氨基酸。由( 1S , 3S )-和( 1R , 3S )-Ac 5 c 3OAll氨基酸组成的钉合八肽显示出右旋α-螺旋晶体结构。

  DOI：

  10.1021/acs.orglett.1c04256
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Val-Val-Val
  参考文献：
  名称：

  Direct modification of tripeptides using photoinduced decarboxylative radical reactions

  摘要：

  In order to explore the applicability of photoinduced electron transfer (PET) promoted decarboxylative reactions to the direct modification of peptides, a study was performed to assess the influence of amino acid side chains on photoreactions of N-terminal protected tripeptides. Photoinduced decarboxylation reactions of tripeptides, which are composed of central amino acids that possess alkyl, phenyl, thioether, hydroxy, and amide containing side chains, in the presence or absence of acrylonitrile and a thiol were found to proceed smoothly to give the corresponding radical addition, H-abstraction, and substitution products. Although photoreactions of tripeptides containing central amino acids with phenol and indole (Tyr and Trp) moieties do not take place efficiently, appropriate protection of these groups enables the substrates to undergo smooth photoinduced decarboxylative reactions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.075

文献信息

• Studies on flavored peptides. VIII. Mechanism for the bitter tasting potency of peptides using O-aminoacyl sugars as model compounds.
  作者：Masahiro TAMURA、Takafumi MIYOSHI、Naoko MORI、Keisuke KINOMURA、Michihiko KAWAGUCHI、Norio ISHIBASHI、Hideo OKAI

  DOI：10.1271/bbb1961.54.1401

  日期：——

  In order to study the role of hydrophobicity in bitter peptides, several O-aminoacyl sugars, in which amino acids or peptides were attached to the 2- and 3-position of methyl α-D-glucopyranoside, were synthesized and sensory analyses were carried out. It was found that the bitterness increased as the hydrophobicity of compounds increased, implying that the bitterness receptor recognizes the hydrophobicity of bitter peptides. A structure for the bitterness receptor is also discussed.

  为了研究疏水性在苦味肽中的作用，合成了几种 O-氨基酰基糖，其中氨基酸或肽附着在甲基 α-D 吡喃葡萄糖苷的 2 位和 3 位上，并进行了感官分析。结果发现，随着化合物疏水性的增加，苦味也随之增加，这意味着苦味受体能识别苦味肽的疏水性。此外，还讨论了苦味受体的结构。
• AMINO ACID AND PEPTIDE INHIBITORS OF HUMAN LEUCOCYTIC ELASTASE
  申请人：LA TROBE UNIVERSITY

  公开号：EP0204775A1

  公开（公告）日：1986-12-17
• EP0204775A4
  申请人：——

  公开号：EP0204775A4

  公开（公告）日：1989-10-04
• [EN] AMINO ACID AND PEPTIDE INHIBITORS OF HUMAN LEUCOCYTIC ELASTASE
  申请人：——

  公开号：WO1986003746A1

  公开（公告）日：1986-07-03

  [EN] Potent and specific inhibitor compounds for elastase - type enzymes, especially for human leucocytic elastase (HLE), are provided by combining an amino acid or short peptide with a hydrocarbon-oxycarbonyl protecting group having at least 4 carbon atoms at the N-terminal of the amino acid or peptide, and a hydrophobic hydrocarbon chain of 8 to 16 carbon atoms at the carbonyl group of the amino acid or peptide, the protecting group and the hydrophobic group being physiologically innocuous components, but providing the required inhibition. The inhibitor compounds can be expected to be useful in the treatment of elastase - type implicated diseases such as arthritis, tumor growth and emphysema.
  [FR] Des composés inhibiteurs puissants et spécifiques pour les enzymes du type élastase, en particulier pour l'élastase leucocytique humaine (HLE), sont obtenus en combinant un amino-acide ou un peptide court avec un groupe de protection des hydrocarbure-oxycarbonyle possédant au moins 4 atomes de carbone au terminal N de l'amino-acide ou du peptide, et une chaîne d'hydrocarbures hydrophobes de 8 à 16 atomes de carbone au groupe des carbonyles de l'amino-acide ou du peptide, le groupe de protection et le groupe hydrophobe étant des composants physiologiquement inoffensifs, mais assurant l'inhibition voulue. On peut s'attendre à ce que ces composés inhibiteurs soeint utiles dans le traitement de maladies du type influencé par l'élastase comme l'arthrite, les tumeurs et l'emphysème.
• [EN] AMINO ACID AND PEPTIDE INHIBITORS OF HUMAN LEUKOCYTIC ELASTASE AND COLLAGENASE
  申请人：——

  公开号：WO1990005141A1

  公开（公告）日：1990-05-17

  [EN] Potent and specific inhibitor compounds for collagenase and/or elastase - type enzymes, especially for human leucocytic elastase (HLE), are provided by combining an amino acid or short peptide with a hydrocarbonyl-oxycarbonyl protecting group having at least 4 carbon atoms at the N-terminal of the amino acid or peptide, and a hydrophobic hydrocarbon chain of 8 to 16 carbon atoms at the carbonyl group of the amino acid or peptide, the protecting group and the hydrophobic group being physiologically innocuous components, but providing the required inhibition. The inhibitor compounds can be expected to be useful in the treatment of collagenase or elastase - type implicated diseases such as arthritis, tumour growth, epidermolysis bullosa, pulmonary emphysema, and chronic obstructive lung disease.
  [FR] Composés inhibiteurs puisssants et spécifiques pour des enzymes du type collagénase et/ou élastase, et notamment pour l'élastase leucocytaire humaine (HLE). On obtient ces composés en combinant un amino acide ou un peptide court avec un groupe protecteur oxycarbonyle d'hydrocarbures comportant au moins quatre atomes de carbone au niveau de la terminaison N de l'amino acide ou du peptide, ainsi qu'avec une chaîne d'hydrocarbures hydrophobes comportant 8 à 16 atomes de carbone au niveau du groupe carbonyle de l'amino acide ou du peptide. Tout en étant des composés physiologiquement inoffensifs, le groupe protecteur et le groupe hydrophobe assurent l'action inhibitrice requise. De tels composés inhibiteurs sont présumés utiles dans le traitement des maladies où sont impliquées des enzymes du type collagénase élastase, telles que l'arthrite, le développement des tumeurs, le pemfigus héréditaire, l'emphysème pulmonaire et les maladies obstructives des poumons de type chronique.