carbobenzoxy-(S)-valyl-(S)-tryptophan methyl ester | 17430-65-8

• 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: carbobenzoxy-(S)-valyl-(S)-tryptophan methyl ester
• 英文别名: Z-L-Val-L-Trp-OMe；(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-3-(1H-indol-3-yl)propanoate；Cbz-Val-Trp-OMe；(S,S)-methyl 2-(2-benzyloxycarbonylamino-3-methylbutanoylamino)-3-(indol-3-yl)-propanoate；Z-Val-Trp-OMe；methyl (2S)-3-(1H-indol-3-yl)-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate
• CAS: 17430-65-8
• 化学式: C₂₅H₂₉N₃O₅
• 分子量: 451.522
• InChiKey: GMCXBLPYMWJNTF-VXKWHMMOSA-N

物化性质

• 沸点：
  695.6±55.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  carbobenzoxy-(S)-valyl-(S)-tryptophan methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 29.0h， 生成 N-((2-hydroxy-1-naphthyl)methylene)-(S)-valyl-(S)-tryptophan methyl ester
  参考文献：
  名称：

  Nitta, Hideaki; Yu, Donghai; Kudo, Masanobu, Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 7969 - 7975

  摘要：

  DOI：
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.25h， 生成 carbobenzoxy-(S)-valyl-(S)-tryptophan methyl ester
  参考文献：
  名称：

  使用TIPS-EBX在肽中金催化的色氨酸直接烷基化。

  摘要：

  仅包含天然氨基酸的肽的选择性功能化对于修饰生物分子很重要。特别地，将炔烃作为用于生物缀合的有用手柄的安装极具吸引力，但是通常需要使用碳连接基。在此，我们报告了使用高价碘试剂TIPS-EBX（1-[（三异丙基甲硅烷基）乙炔基] -1，2-苯并恶多酚-3（1H）-一）在肽中金催化的色氨酸直接烷基化。反应在温和的条件下以50-78％的收率进行，可用于含有其他亲核和芳香族氨基酸（如丝氨酸，苯丙氨酸或酪氨酸）的肽。

  DOI：

  10.3762/bjoc.12.74

文献信息

• Diazonamide studies. A direct synthesis of the indole bis-oxazole fragment from tri- and tetra-peptides using biomimetic oxidative cyclizations
  作者：Jonathan Sperry、Christopher J. Moody

  DOI：10.1016/j.tet.2010.03.012

  日期：2010.8

  oxidation of several readily prepared tryptophan containing tri- and tetrapeptides with DDQ results in a biomimetic cyclization and direct formation of the indole bis-oxazole fragment of diazonamide A, establishing that such a transformation is a viable route when considering the biosynthetic formation of the heterocyclic core of the natural product.

  几个容易制备的含有色氨酸的三肽和四肽用DDQ的氧化导致仿生环化反应和重氮酰胺A的吲哚双恶唑片段的直接形成，从而在考虑杂环的生物合成形成时，确定这种转化是可行的途径天然产品的核心。
• Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification
  作者：Eliott Le Du、Marion Garreau、Jérôme Waser

  DOI：10.1039/d0sc06180h

  日期：——

  photoredox-catalyzed oxidative decarboxylative coupling of small peptides is reported, giving access to a variety of N,O-acetals. They were used as intermediates for the addition of phenols and indoles, leading to novel peptide scaffolds and bioconjugates. Amino acids with nucleophilic side chains, such as serine, threonine, tyrosine and tryptophan, could also be used as partners to access tri- and tetrapeptide derivatives

  报道了光氧化还原催化的小肽氧化脱羧偶联，从而获得多种N , O-缩醛。它们被用作添加酚和吲哚的中间体，从而产生新型肽支架和生物缀合物。具有亲核侧链的氨基酸，例如丝氨酸、苏氨酸、酪氨酸和色氨酸，也可以用作伙伴来获得具有非天然交联的三肽和四肽衍生物。
• New peptides and a process for their preparation
  申请人：Hoechst Aktiengesellschaft

  公开号：US04420424A1

  公开（公告）日：1983-12-13

  What are disclosed are pentapeptides, useful for influencing the maturing of T-lymphocytes, of the formula G--K--Q--X--M wherein G is arginine, lysine, ornithine, or homoarginine, or is an unsubstituted or substituted .omega.-aminoalkanoyl, .omega.-guanidinoalkanoyl, or .omega.-dimethylaminoalkanoyl; K is a basic amino acid such as lysine, arginine, homoarginine, or ornithine; Q is L- or D-glutamic acid, d-aspartic acid, or D-.alpha.-aminoadipic acid; X is L-valine or L-isoleucine; and M is an L- or D-aminoacid having a hydrophobic side chain, or an ester or amide of such an acid.

  所披露的是五肽，用于影响T淋巴细胞的成熟，其化学式为G-K-Q-X-M，其中G为精氨酸、赖氨酸、鸟氨酸或同型精氨酸，或为未取代或取代的ω-氨基烷酰基、ω-胍基烷酰基或ω-二甲基氨基烷酰基；K为一种碱性氨基酸，如赖氨酸、精氨酸、同型精氨酸或鸟氨酸；Q为L-或D-谷氨酸、D-天冬氨酸或D-α-氨基己二酸；X为L-缬氨酸或L-异亮氨酸；M为一种具有疏水侧链的L-或D-氨基酸，或该酸的酯或酰胺。
• Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides
  作者：Noriaki. Funasaki、Sakae. Hada、Saburo. Neya

  DOI：10.1021/ac00062a010

  日期：1993.7.15

  The capacity factors, k', of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k' values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k'LL is larger than k'LD, and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k'LL is smaller than k'DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k' values of larger peptides and the hydrophobicity and related properties of peptides.
• PEPTIDOMIMETIC MODULATORS OF CELL ADHESION
  申请人：Gour J. Barbara

  公开号：US20080081831A1

  公开（公告）日：2008-04-03

  Peptidomimetics of cyclic peptides, and compositions comprising such peptidomimetics are provided. The peptidomimetics have a three-dimensional structure that is substantially similar to a three-dimensional structure of a cyclic peptide that comprises a cadherin cell adhesion recognition sequence HAV. Methods for using such peptidomimetics for modulating cadherin-mediated cell adhesion in a variety of contexts are also provided.