L-异亮13C6,15N | 202468-35-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 异亮氨酸类衍生物
• 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: L-异亮13C6,15N
• 英文名称: [13C6,15N]-L-isoleucine
• 英文别名: L-Isoleucine-13C6, 15N；(2S,3S)-2-(15N)azanyl-3-(113C)methyl(1,2,3,4,5-13C5)pentanoic acid
• CAS: 202468-35-7
• 化学式: C₆H₁₃NO₂
• 分子量: 138.102
• InChiKey: AGPKZVBTJJNPAG-PVHYACKGSA-N

物化性质

• 熔点：
  168-170 °C(lit.)
• 溶解度：
  酸水溶液（少量溶解）、甲醇（少量、加热、超声处理）、水（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

制备方法与用途

L-异亮氨酸-13C6,15N 是一种带有13C和15N标记的L-异亮氨酸。L-异亮氨酸是一种非极性疏水氨基酸，同时也是必需氨基酸。

反应信息

• 作为反应物：
  描述：

  L-异亮13C6,15N 在 1H-咪唑-1-磺酰叠氮盐酸盐 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以66%的产率得到(2S,3S)-2-(azido-1-15N)-3-(methyl-13C)pentanoic-1,2,3,4,5-13C5 acid
  参考文献：
  名称：

  Mechanistic studies on the diazo transfer reaction

  摘要：

  The mechanism of the diazo transfer reaction which converts amines to azides has been studied with labeled amino acids and labeled imidazole-l-sulfonyl azides. Retention of amine nitrogen in the amine, and transfer of the two terminal nitrogen atoms of the imidazole-l-sulfonyl azide to the product, were unambiguously established. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.057

文献信息

• [EN] METHODS FOR SELECTIVELY MODIFYING AMINO ACIDS AND PRODUCTS MADE THEREBY<br/>[FR] PROCÉDÉS DE MODIFICATION SÉLECTIVE D'ACIDES AMINÉS ET PRODUITS FABRIQUÉS PAR CEUX-CI
  申请人：UNIV CALIFORNIA

  公开号：WO2021007127A1

  公开（公告）日：2021-01-14

  Disclosed herein are methods for the selective substitution of a hydrogen bonded to a carbon atom (e.g., a hydrogen of an aliphatic methylene group) of a compound, which comprise contacting the compound with a substituent in the presence of a BesD halogenase.

  本文披露了一种选择性替代化合物中与碳原子结合的氢（例如，脂肪族亚甲基基团的氢）的方法，包括在BesD卤素酶存在的情况下将化合物与取代基接触。
• Biosynthesis and in vitro enzymatic synthesis of the isoleucine conjugate of 12-oxo-phytodienoic acid from the isoleucine conjugate of α-linolenic acid
  作者：Akira Uchiyama、Takaomi Yaguchi、Hiroyuki Nakagawa、Kento Sasaki、Naoshige Kuwata、Hideyuki Matsuura、Kosaku Takahashi

  DOI：10.1016/j.bmcl.2018.02.030

  日期：2018.4

  OPDA-Ile remains elusive. This study reports an in vitro enzymatic method for synthesizing OPDA-Ile, which is catalyzed by reactions of lipoxygenase (LOX), allene oxide synthase (AOS), and allene oxide cyclase (AOC) using isoleucine conjugates of α -linolenic acid (LA-Ile) as the substrate. A. thaliana fed LA-Ile exhibited a marked increase in the OPDA-Ile concentration. LA-Ile was also detected in A

  最近在拟南芥中鉴定了茉莉酸家族的新成员12-氧代-植物二烯酸（OPDA-Ile）的异亮氨酸缀合物，它可能是植物中的信号分子。然而，OPDA-Ile的生物合成和功能仍然难以捉摸。这项研究报告了一种体外酶法合成OPDA-Ile的方法，该方法通过使用α-亚麻酸（LA- Ile）作为底物。饲喂LA-Ile的拟南芥显示出ODPA-Ile浓度的显着增加。在拟南芥中也检测到了LA-Ile 。此外，将稳定同位素标记的LA-Ile掺入OPDA-Ile。因此，通过在拟南芥中LA-Ile的环化来生物合成OPDA-Ile 。
• Development of a Stable Isotope Dilution Assay for Tenuazonic Acid
  作者：Stefan Asam、Yang Liu、Katharina Konitzer、Michael Rychlik

  DOI：10.1021/jf104270e

  日期：2011.4.13

  A stable isotope dilution assay (SIDA) for the Alternaria mycotoxin tenuazonic acid was developed. Therefore, [C-13(6),N-15]-tenuazonic acid was synthesized from [C-13(6),N-15]-isoleucine by Dieckmann intramolecular cyclization after acetoacetylation with diketene. The synthesized [C-13(6),N-15]-tenuazonic acid was used as the internal standard for determination of tenuazonic acid in tomato products by liquid chromatography tandem mass spectrometry after derivatization with 2,4-dinitrophenylhydrazine. Method validation revealed a limit of detection of 0.1 mu g/kg and a limit of quantitation of 0.3 mu g/kg. Recovery was close to 100% in the range of 3-300 mu g/kg. Determination of tenuazonic acid in two samples of different tomato ketchups (naturally contaminated) was achieved with a coefficient of variation of 2.3% and 4.7%. Different tomato products (n = 16) were analyzed for their content of tenuazonic acid using the developed SIDA. Values were between 15 and 195 mu g/kg (tomato ketchup, n = 9), 363 and 909 mu g/kg (tomato paste, n = 2), and 8 and 247 mu g/kg (pureed tomatoes and comparable products, n = 5).