L-酪氨酸-3-13C | 129077-96-9

• 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
• 中文名称: L-酪氨酸-3-13C
• 中文别名: L-4-羟基苯基丙氨酸-3-13C
• 英文名称: 3-(13)C-tyrosine
• 英文别名: L-[3-(13)C]tyrosine；L-Tyrosine-3-13C；(2S)-2-amino-3-(4-hydroxyphenyl)(313C)propanoic acid
• CAS: 129077-96-9
• 化学式: C₉H₁₁NO₃
• 分子量: 182.18
• InChiKey: OUYCCCASQSFEME-LDSMRRTFSA-N

物化性质

• 熔点：
  >300 °C (dec.)(lit.)

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

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

反应信息

• 作为反应物：
  描述：

  L-酪氨酸-3-13C 在 tyrosine decarboxylase 作用下， 反应 8.0h， 以42 mg的产率得到[2-(13)C]tyramine
  参考文献：
  名称：

  Biosynthesis of acteoside in cultured cells of Olea europaea

  摘要：

  我们从油橄榄的细胞悬浮培养物中分离出了五种苯乙醇苷（槲皮苷、异槲皮苷、β-氧代槲皮苷、β-羟基槲皮苷和水杨梅苷）。通过使用稳定同位素标记的前体进行喂养实验，我们研究了橄榄细胞培养物中肌动苷的生物合成。猕猴桃苷的羟基酪醇分子是通过多巴胺从酪氨酸中生物合成的，而猕猴桃苷的咖啡酰分子则是通过肉桂酸途径从苯丙氨酸中生物合成的。多巴胺通过氧化成相应的醛、还原成醇，然后再进行β-糖基化，从而与肌动苷结合。

  DOI：

  10.1007/s11418-009-0383-z
• 作为产物：
  描述：

  (3R,5S)-2,3,5,6-tetrahydro-3-[4-(methoxymethyloxy)phenyl[13C]methyl]-5-phenyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、588.36 kPa 条件下， 反应 56.5h， 生成 L-酪氨酸-3-13C
  参考文献：
  名称：

  由[ 13 C]一氧化碳不对称合成1- [3- 13 C]苯丙氨酸和1- [3- 13 C]酪氨酸

  摘要：

  合成了1- [3- 13 C]苯丙氨酸和1- [3- 13 C]酪氨酸。[α- 13是从[制备C]苄基溴化物13 C]一氧化碳通过芳基卤化物的钯催化carboalkoxylation。对应于苯丙氨酸2-位的不对称碳是由Dellaria的恶嗪酮的非对映烷基化引入的[α- 13 C]苄基溴化物。最后，所得烷基化的恶嗪酮的乙醇解，脱保护，氢解和酸水解以高光学纯度得到1- [3- 13 C]苯丙氨酸和1- [3- 13 C]酪氨酸。

  DOI：

  10.1016/s0040-4020(98)00995-8

文献信息

• Quantitation of Dityrosine in Wheat Flour and Dough by Liquid Chromatography−Tandem Mass Spectrometry
  作者：Franziska Hanft、Peter Koehler

  DOI：10.1021/jf048005t

  日期：2005.4.1

  A method for the quantitation of dityrosine in wheat flour and dough by high-performance liquid chromatography/tandem mass spectrometry (HPLC-MS/MS) using an isotope dilution assay with the internal standard 3,3'-C-13(2)-dityrosine in the single-reaction monitoring mode was developed. The method consisted of the release of protein-bound dityrosine by hydrolysis in 4 mol/L hydrochloric acid/8.9 mol/L propionic acid for 24 h at 110 degrees C after addition of the internal standard, cleanup by C-18 solid-phase extraction, and HPLC-MS/MS. The limit of detection of dityrosine was 80 ng/g of sample (0.22 nmol/g), and the limit of quantitation was 270 ng/g of sample (0.75 nmol/g). The method was sensitive enough to analyze wheat flour and dough and to study the effect of flour improvers on the dityrosine content. Furthermore, the effect of the mixing time was studied. The dityrosine concentration in the flour was 0.66 nmol/g. After we mixed a dough to peak consistency, the dityrosine concentration doubled and remained constant on further mixing. Overdoses of hydrogen peroxide and hexose oxidase (HOX, E.C. 1.1.3.5) resulted in a strongly increased dityrosine content, whereas no increase of the dityrosine concentration was found after the addition of ascorbic acid and potassium bromate. Calculation of the percentage of dimeric tyrosine showed that less than 0.1% of the tyrosine residues of wheat protein were cross-linked. Therefore, dityrosine residues seem to play only a very minor role in the structure of wheat gluten.
• Bjurling, Peter; Watanabe, Yasuyoshi; Oka, Shogo, Acta Chemica Scandinavica, 1990, vol. 44, # 2, p. 183 - 188
  作者：Bjurling, Peter、Watanabe, Yasuyoshi、Oka, Shogo、Nagasawa, Toru、Yamada, Hideaki、Langstroem, Bengt

  DOI：——

  日期：——
• An asymmetric synthesis of l-[3-13C]phenylalanine and l-[3-13C]tyrosine from [13C]carbon monoxide
  作者：Kazuhiko Takatori、Mikiko Nishihara、Yukie Nishiyama、Masahiro Kajiwara

  DOI：10.1016/s0040-4020(98)00995-8

  日期：1998.12

  l-[3-13C]Phenylalanine and l-[3-13C]tyrosine were synthesized. [α-13C]Benzyl bromides were prepared from [13C]carbon monoxide via the palladium-catalyzed carboalkoxylation of aryl halides. The asymmetric carbon corresponding to the 2-position in phenylalanine was introduced by the diastereoselective alkylation of Dellaria's oxazinone with [α-13C]benzyl bromides. Finally, ethanolysis, deprotection,

  合成了1- [3- 13 C]苯丙氨酸和1- [3- 13 C]酪氨酸。[α- 13是从[制备C]苄基溴化物13 C]一氧化碳通过芳基卤化物的钯催化carboalkoxylation。对应于苯丙氨酸2-位的不对称碳是由Dellaria的恶嗪酮的非对映烷基化引入的[α- 13 C]苄基溴化物。最后，所得烷基化的恶嗪酮的乙醇解，脱保护，氢解和酸水解以高光学纯度得到1- [3- 13 C]苯丙氨酸和1- [3- 13 C]酪氨酸。
• Biosynthesis of acteoside in cultured cells of Olea europaea
  作者：Hiroshi Saimaru、Yutaka Orihara

  DOI：10.1007/s11418-009-0383-z

  日期：2010.4

  Five phenylethanoid glycosides (acteoside, isoacteoside, β-oxoacteoside, β-hydroxyacteoside, and salidroside) were isolated from a cell suspension culture of Olea europaea. We examined the biosynthesis of acteoside in olive cell cultures by using feeding experiments with stable isotope labeled precursors. The hydroxytyrosol moiety of acteoside is biosynthesized from tyrosine through dopamine, whereas the caffeoyl moiety of acteoside is biosynthesized from phenylalanine via a cinnamate pathway. Dopamine is incorporated into acteoside through oxidation to the corresponding aldehyde, reduction to the alcohol, and then β-glycosylation.

  我们从油橄榄的细胞悬浮培养物中分离出了五种苯乙醇苷（槲皮苷、异槲皮苷、β-氧代槲皮苷、β-羟基槲皮苷和水杨梅苷）。通过使用稳定同位素标记的前体进行喂养实验，我们研究了橄榄细胞培养物中肌动苷的生物合成。猕猴桃苷的羟基酪醇分子是通过多巴胺从酪氨酸中生物合成的，而猕猴桃苷的咖啡酰分子则是通过肉桂酸途径从苯丙氨酸中生物合成的。多巴胺通过氧化成相应的醛、还原成醇，然后再进行β-糖基化，从而与肌动苷结合。