[U-13C, 15N]-L-tyrosine | 202407-26-9

• 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: [U-13C, 15N]-L-tyrosine
• 英文别名: L-Tyrosine-13C9,15N；(2S)-2-(15N)azanyl-3-(4-hydroxy(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl)(1,2,3-13C3)propanoic acid
• CAS: 202407-26-9
• 化学式: C₉H₁₁NO₃
• 分子量: 191.086
• InChiKey: OUYCCCASQSFEME-CMLFETTRSA-N

物化性质

• 熔点：
  >300 °C (dec.)(lit.)
• 溶解度：
  酸水溶液（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 储存条件：
  存于室温下，请密封并保持干燥。

制备方法与用途

DL-酪氨酸-13C9,15N 是一种 13C 和 15N 标记的 DL-酪氨酸。DL-酪氨酸是一种芳香族非必需氨基酸，由必需氨基酸苯丙氨酸合成。它还是肾上腺素、去甲肾上腺素和多巴胺等多种重要神经递质的前体物质。

反应信息

• 作为反应物：
  描述：

  [U-13C, 15N]-L-tyrosine 在 吡啶 、 盐酸 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 copper diacetate 、 一氯化碘 、 碳酸氢钠 、 正丁胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.33h， 生成 methyl (2S)-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino](1,2,3-13C3)propanoate
  参考文献：
  名称：

  The Synthesis of ¹³C₉-¹⁵N-Labeled 3,5-Diiodothyronine and Thyroxine

  摘要：

  Thyroid hormones undergo extensive metabolism to regulate hormone activity. A labeled thyroid hormone would be useful to track hormone metabolism through various pathways. While radiolabeled thyroid hormones have been synthesized and used for in vivo studies, a stable isotope labeled form of thyroid hormone is required for studying thyroid hormone metabolism by LC-MS/MS, an analytical technique that has certain advantages without the complications of radioactivity. Here we report the synthesis of 13C9-15N-T2 and 13C9-15N-T4, two labeled thyroid hormone derivatives suitable for in vivo LC-MS/MS studies. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.639005

文献信息

• Derivatize, Racemize, and Analyze—an Easy and Simple Procedure for Chiral Amino Acid Standard Preparation for Enantioselective Metabolomics
  作者：Jeannie Horak、Michael Lämmerhofer

  DOI：10.1021/acs.analchem.9b00666

  日期：2019.6.18

  epimerization) protocol for the preparation of scalemic α-amino acid mixtures from stereoisomerically pure standards was developed. Simply derivatize your amino acids with a racemization tag that incorporates a urea bond on the N-terminus of the target amino acid and incubate at elevated temperatures up to 95 °C for defined time periods until the targeted d-amino acid levels are obtained. The racemization

  开发了一种简单，可控制和可重现的立体异构化方法（消旋和差向异构化），用于从立体异构纯标准品制备规模化α-氨基酸混合物。只需使用消旋标签衍生化您的氨基酸即可，该消旋标签在目标氨基酸的N-末端掺有尿素键，并在高达95°C的高温下孵育一段确定的时间，直至获得目标d-氨基酸水平。研究的外消旋标记是6-氨基喹啉基-N-羟基琥珀酰亚胺基氨基甲酸酯（AQC），氨基苯基-N-羟基琥珀酰亚胺基氨基甲酸酯（AC）和3-氨基吡啶基-N氨基甲酸-羟基琥珀酰亚胺基酯（APC）。采用这种方法，可以在数分钟内或在几分钟内，制备出可立即使用的，量身定制的，手性均匀的13 C和15 N标记的[U - 13 C 15 N]-氨基酸标准品，并具有所需的d-氨基酸百分比。小时不进行样品清理。在95°C下消旋30分钟的消旋时间将导致d-氨基酸水平为1-5％，而在95°C下6 h消旋时间将提供15-30％的d-氨基酸。外消旋化是由于
• [FeFe]-Hydrogenase Cyanide Ligands Derived From S-Adenosylmethionine-Dependent Cleavage of Tyrosine
  作者：Rebecca C. Driesener、Martin R. Challand、Shawn E. McGlynn、Eric M. Shepard、Eric S. Boyd、Joan B. Broderick、John W. Peters、Peter L. Roach

  DOI：10.1002/anie.200907047

  日期：2010.2.22

  What's your poison? Hydrogenases catalyze the reversible formation of dihydrogen from two electrons and two protons. The maturation of the [FeFe]‐hydrogenase active‐site cofactor (H cluster) requires three gene products, HydE, HydF, and HydG. Cyanide has been characterized as one of the products of tyrosine cleavage by the S‐adenosylmethionine‐dependent enzyme HydG, clarifying its role in H‐cluster

  你的毒药是什么？氢酶催化由两个电子和两个质子可逆地形成二氢。[FeFe]-加氢酶活性位点辅酶（H簇）的成熟需要三个基因产物，即HydE，HydF和HydG。氰化物已被S-腺苷甲硫氨酸依赖性酶HydG裂解为酪氨酸的产物之一，从而阐明了其在H簇生物合成中的作用。DOA =脱氧腺苷。
• The Synthesis of ¹³C₉-¹⁵N-Labeled 3,5-Diiodothyronine and Thyroxine
  作者：Sarah A. Hackenmueller、Thomas S. Scanlan

  DOI：10.1080/00397911.2011.639005

  日期：2013.5.15

  Thyroid hormones undergo extensive metabolism to regulate hormone activity. A labeled thyroid hormone would be useful to track hormone metabolism through various pathways. While radiolabeled thyroid hormones have been synthesized and used for in vivo studies, a stable isotope labeled form of thyroid hormone is required for studying thyroid hormone metabolism by LC-MS/MS, an analytical technique that has certain advantages without the complications of radioactivity. Here we report the synthesis of 13C9-15N-T2 and 13C9-15N-T4, two labeled thyroid hormone derivatives suitable for in vivo LC-MS/MS studies. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.