2-氨基-3-叠氮基丙酸 | 105661-40-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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
• 中文名称: 2-氨基-3-叠氮基丙酸
• 英文名称: L-azidoalanine hydrochloride
• 英文别名: β-azido-L-alanine；3-azido-L-alanine；L-azido alanine；L-azidoalanine；azidoalanine；(2S)-2-amino-3-azidopropanoic acid
• CAS: 105661-40-3
• 化学式: C₃H₆N₄O₂
• 分子量: 130.106
• InChiKey: CIFCKCQAKQRJFC-REOHCLBHSA-N

物化性质

• 熔点：
  174-175 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-3-叠氮基丙酸 在 硫酸 、 水 、 sodium nitrite 作用下， 以26%的产率得到(2S)-N3-IsoSer
  参考文献：
  名称：

  [EN] BIOLUMINESCENCE IMAGING OF SMALL BIOMOLECULES
  [FR] IMAGERIE PAR BIOLUMINESCENCE DE BIOMOLÉCULES DE PETITE TAILLE

  摘要：

  这项发明涉及一种利用生物发光成像（BLI）来检测小分子的技术，以非侵入性地在体外和体内成像和定量细胞内代谢物通量，并可应用于含有偶氮修饰的化合物，如偶氮修饰的生物分子。

  公开号：

  WO2014111906A1
• 作为产物：
  描述：

  (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid 在 triflic azide 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以60%的产率得到2-氨基-3-叠氮基丙酸
  参考文献：
  名称：

  Presentation and Detection of Azide Functionality in Bacterial Cell Surface Proteins

  摘要：

  An improved protocol for copper-catalyzed triazole formation on the bacterial cell surface is described. Addition of highly pure CuBr to cells treated with azidohomoalanine (2) leads to ca. 10-fold more extensive cell surface labeling than previously observed. This highly active catalyst allows detection of the methionine analogues azidoalanine (1), azidonorvaline (3), and azidonorleucine (4) in cell surface proteins. Azidoalanine was previously believed to be silent with regard to the cellular protein synthesis machinery.

  DOI：

  10.1021/ja047629c

文献信息

• Diaminodiacid-based synthesis of macrocyclic peptides using 1,2,3-triazole bridges as disulfide bond mimetics
  作者：Ye Guo、Chao Liu、Hui Song、Feng-Liang Wang、Yan Zou、Qiu-Ye Wu、Hong-Gang Hu

  DOI：10.1039/c6ra26617g

  日期：——

  A new approach for the efficient construction of 1,2,3-triazole bridges as disulfide surrogates in peptides, utilizing the diaminodiacid strategy was established. Two thanatin derivatives were prepared with 1,5- and 1,4-disubstituted 1,2,3-triazole diaminodiacids as building blocks. The antibacterial activity studies are also described here.

  建立了一种利用二氨基二酸策略有效构建1,2,3-三唑桥作为肽中的二硫化物替代物的新方法。用1，5-和1，4-二取代的1,2,3-三唑二氨基二酸作为结构单元制备了两种他汀衍生物。此处还描述了抗菌活性研究。
• Synthesis of optically pure .alpha.-amino acids via salts of .alpha.-amino-.beta.-propiolactone
  作者：Lee D. Arnold、Robert G. May、John Christopher. Vederas

  DOI：10.1021/ja00215a038

  日期：1988.3

  Recyclage du charbon active granuleux utilise dans le traitement des eaux potables par un procede de four a lit fluidise et four infrarouge. Etude de la formation de sous produits tels que des polychlorodibenzodioxinnes et des polychlorodibenzofurannes (PC DDS et PC DFS)

  Recyclage du charbon active granuleux 利用 dans le traitement des eaux potables par un procede de 4 a lit fluidise et 4 infrarouge。Etude de laformation de sous produits tels que des polychlorodibenzodioxinnes et des polychlorodibenzofuranes (PC DDS et PC DFS)
• Syntheses of optically pure .alpha.-amino acids from 3-amino-2-oxetanone
  申请人：The Governors of the University of Alberta

  公开号：US05200526A1

  公开（公告）日：1993-04-06

  A process for the preparation of optically pure .alpha.-amino acids comprising the nucleophilic ring-opening of 3-amino-2-oxetanone salts. N-Protected serine .beta.-lactones are deprotected to form heretofore unknown 3-amino-2-oxetanone and its corresponding salts. In turn these previously unknown 3-amino-2-oxetanone salts may be used in the synthesis of other novel or rare stereochemically-pure free amino acids.

  一种制备光学纯α-氨基酸的方法，包括对3-氨基-2-氧杂环酮盐进行亲核环开反应。去保护的丝氨酸β-内酰胺脱保护后形成迄今未知的3-氨基-2-氧杂环酮及其相应的盐。反过来，这些先前未知的3-氨基-2-氧杂环酮盐可用于合成其他新型或罕见的立体化学纯自由氨基酸。
• Metabolic Synthesis of Clickable Glutathione for Chemoselective Detection of Glutathionylation
  作者：Kusal T. G. Samarasinghe、Dhanushka N. P. Munkanatta Godage、Garrett C. VanHecke、Young-Hoon Ahn

  DOI：10.1021/ja503946q

  日期：2014.8.20

  Glutathionylation involves reversible protein cysteine modification that regulates the function of numerous proteins in response to redox stimuli, thereby altering cellular processes. Herein we developed a selective and versatile approach to identifying glutathionylation by using a mutant of glutathione synthetase (GS). GS wild-type catalyzes coupling of γGlu-Cys to Gly to form glutathione. We generated a GS mutant that catalyzes azido-Ala in place of Gly with high catalytic efficiency and selectivity. Transfection of this GS mutant (F152A/S151G) and incubation of azido-Ala in cells efficiently afford the azide-containing glutathione derivative, γGlu-Cys-azido-Ala. Upon H2O2 treatment, clickable glutathione allowed for selective and sensitive detection of glutathionylated proteins by Western blotting or fluorescence after click reaction with biotin-alkyne or rhodamine-alkyne. This approach affords the efficient metabolic tagging of intracellular glutathione with small clickable functionality, providing a versatile handle for characterizing glutathionylation.
• “Click to Chelate”:  Synthesis and Installation of Metal Chelates into Biomolecules in a Single Step
  作者：Thomas L. Mindt、Harriet Struthers、Luc Brans、Todor Anguelov、Christian Schweinsberg、Veronique Maes、Dirk Tourwé、Roger Schibli

  DOI：10.1021/ja066779f

  日期：2006.11.1

  Click chemistry has been employed for the assembly of novel and efficient triazole-based multidentate chelating systems while simultaneously attaching them to molecules of biological interest. The "click-to-chelate" approach offers a powerful new tool for the modification of (bio)molecules with metal chelators for potential diagnostic and therapeutic applications.