(2S)-2-氨基-3-(1-芘基)丙酸 | 87147-90-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: (2S)-2-氨基-3-(1-芘基)丙酸
• 英文名称: L-3-(1-pyrenyl)alanine
• 英文别名: L-1-pyrenylalanine；PyrAla；1-Pyrenylalanine；(2S)-2-amino-3-pyren-1-ylpropanoic acid
• CAS: 87147-90-8
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: VTMOPDBUZPBOPL-INIZCTEOSA-N

物化性质

• 熔点：
  205-210 °C
• 沸点：
  531.9±38.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-氨基-3-(1-芘基)丙酸 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 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 Boc-Pro-Pya-Pro-Ile-Ile-Val-OBzl
  参考文献：
  名称：

  Studies on Bitter Peptides from Casein Hydrolyzate. XIV. Bitter Taste of Synthetic Analogs of Octapeptide, Arg–Gly–Pro–Phe–Pro–Ile–Ile–Val, Corresponding to the C-Terminal Portion ofβ-Casein

  摘要：

  为了阐明β-酪蛋白C端部分的化学结构与其苦味之间的关系，合成了一些类似物，其中酪氨酸残基被d-酪氨酸、赖氨酸、甘氨酸、谷氨酸或l-吡咯啉酪氨酸替代。感觉分析和圆二色谱（CD谱）显示，在两个脯氨酸残基之间的位置上，具有l-构型的疏水氨基酸对这一系列肽产生强苦味的重要性。

  DOI：

  10.1246/bcsj.67.438
• 作为产物：
  描述：

  1-芘甲醇 在 氢氧化钾 、 sodium hydroxide 、 aminoacylase 、 三溴化磷 、 sodium hydride 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 苯 为溶剂， 反应 88.0h， 生成 (2S)-2-氨基-3-(1-芘基)丙酸
  参考文献：
  名称：

  A Non-Covalent Strategy for the Assembly of Supramolecular Photocurrent-Generating Systems

  摘要：

  Three photocurrent-generating thin films were assembled on gold surfaces. SAM I was constructed from molecules consisting of an alkyl disulfide group linked covalently to a 12-residue helical peptide and terminated with an alanine residue containing a pyrene chromophore. SAM I served as a benchmark for multilayered films II and III in photocurrent generation experiments. Films II and III were assembled from several components that were linked noncovalently by metal-ligand complexation. Cyclic voltammetry and contact angle measurements suggest that the films consist of ordered layers with relatively few defects. Photoexcitation of SAM I by the output of a 350 nm lamp ( approximately 0.2 mW power incident on the sample) results in current generation in the range 5-10 nA/cm2. Photoexcitation of II and III yields higher current in the range 10-30 nA/cm2, representing a quantum efficiency of approximately 1%. The observation of comparable or higher current from noncovalently assembled multicomponent films indicates that this method of assembly may obviate the problems associated with the covalent assembly of devices from large molecules.

  DOI：

  10.1021/ja0289548

文献信息

• HIGH-SENSITIVE FLUORESCENT ENERGY TRANSFER ASSAY USING FLUORESCENT AMINO ACIDS AND FLUORESENT PROTEINS
  申请人：The Regents of the University of California

  公开号：US20150369800A1

  公开（公告）日：2015-12-24

  The disclosure provides method and composition utilizing fluorescent amino acids and fluorescent proteins comprising a moiety capable of undergoing FRET. The methods and compositions of the disclosure are useful in analyzing protein structure and function, and screening molecular inhibitors.

  该公开提供了一种利用荧光氨基酸和含有能够进行FRET的荧光蛋白的方法和组合物。该公开的方法和组合物在分析蛋白质结构和功能，以及筛选分子抑制剂方面具有实用性。
• A method for manufacturing optically active coumaryl amino acid salts and the coumaryl aminoacid salts thus obtained
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP1559712A1

  公开（公告）日：2005-08-03

  The present invention relates to the field of the synthesis of optically active amino acids, mainly for the purpose of manufacturing optically active polypeptides that are useful as labelled detection tools. The manufacturing method involves the preparation of optically active coumaryl amino acid salts of formula (I).

  本发明涉及光学活性氨基酸合成领域，主要用于制造作为标记检测工具有用的光学活性多肽。该制造方法涉及制备式(I)的光学活性香豆素氨基酸盐。
• Photoinduced electron transfer on a single .alpha.-helical polypeptide chain
  作者：Masahiko Sisido、Ryo Tanaka、Yoshihito Inai、Yukio Imanishi

  DOI：10.1021/ja00199a044

  日期：1989.8

  Apres avoir fixe des groupes chromophores sur des polypeptides (contenant surtout des glutamates) on etudie le transfert d'electron intramoleculaire le long de l'helice α du peptide. L'etude est effectuee sur le peptide modele Boc-dmaPhe-Ala-pyr Ala-OMe

  在 etudie le transfert d'electron intramoleculaire le long de l'helice α dupeptide 上的固定组发色团 sur des 多肽（contenant surtout des glutamates）。练习曲 est effectuee sur le肽模型 Boc-dmaPhe-Ala-pyr Ala-OMe
• [EN] CYSTEINE ARYLATION DIRECTED BY A GENETICALLY ENCODABLE π-CLAMP<br/>[FR] ARYLATION DE CYSTÉINE DIRIGÉE PAR UN N-CLAMP ENCODABLE GÉNÉTIQUEMENT
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2015175941A1

  公开（公告）日：2015-11-19

  Disclosed are methods of single-site-specific cysteine modification on peptide/protein molecules under physiologically relevant conditions. This process features several significant advantages over existing methods of peptide modification, such as specificity towards thiols over other nucleophiles (e.g., amines, hydroxyls), excellent functional group tolerance, and mild reaction conditions. Especially important is the specificity observed for thiols appearing in an X-Cys-Pro-X sequence over other thiols or disulfides, where X is Phe, Trp, or Tyr; under the inventive conditions, other cysteines or reactive functional groups on the same peptide/protein chain are not functionalized.

  披露了在生理条件下对肽/蛋白分子进行单位点特异性半胱氨酸修饰的方法。该过程具有几个显著优点，相比现有的肽修饰方法，如对硫醇具有特异性而不影响其他亲核试剂（如胺基、羟基）、良好的官能团容忍性和温和的反应条件。尤其重要的是，观察到对出现在X-Cys-Pro-X序列中的硫醇的特异性，而不影响其他硫醇或二硫键，其中X为Phe、Trp或Tyr；在创新的条件下，同一肽/蛋白链上的其他半胱氨酸或反应性官能团不会发生功能化。
• Method for manufacturing optically pure coumaryl amino acids and the novel coumaryl aminoacids thus obtained
  申请人：Garbay Christiane

  公开号：US20070161807A1

  公开（公告）日：2007-07-12

  The present invention relates to the field of the synthesis of optically pure amino acid derivatives, mainly for the purpose of manufacturing optically active polypeptides that are useful as labelled detection tools.

  本发明涉及合成光学纯氨基酸衍生物的领域，主要用于制造作为标记检测工具有用的光学活性多肽。