[13C6]-L-苯丙氨酸 | 180268-82-0

• 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: [13C6]-L-苯丙氨酸
• 中文别名: L-苯基-¹³C₆-丙氨酸；L-苯丙氨酸-13C6
• 英文名称: [ring-13C6]-L-phenylalanine
• 英文别名: phenylalanine-[ring-13C6]；L-Phenylalanine-13C6；(2S)-2-amino-3-((1,2,3,4,5,6-13C6)cyclohexatrienyl)propanoic acid
• CAS: 180268-82-0
• 化学式: C₉H₁₁NO₂
• 分子量: 171.126
• InChiKey: COLNVLDHVKWLRT-KILZIXFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 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：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [13C6]-L-苯丙氨酸 在 盐酸 、 正丁基锂 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 32.42h， 生成 [ring-13C6]-(1(S)-benzyl-3-chloro-2-oxo-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  13C6 标记的​​ Reyataz 的合成？(BMS-232632)

  摘要：

  描述了 13C6 标记的​​ Reyataz™ (BMS-232632) 的有效合成。13C6 标记的​​ Reyataz™ 是由市售的 [环-13C6]-L-苯丙氨酸分八步合成的。合成总收率为8%，最终产品纯度大于98%。版权所有 © 2005 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.905

文献信息

• Alternative Pathway to the Formation of <i>trans</i>-Cinnamic Acid Derived from <scp>l</scp>-Phenylalanine in Tea (<i>Camellia sinensis</i>) Plants and Other Plants
  作者：Lanting Zeng、Xiaoqin Wang、Haibo Tan、Yinyin Liao、Ping Xu、Ming Kang、Fang Dong、Ziyin Yang

  DOI：10.1021/acs.jafc.9b07467

  日期：2020.3.18

  trans-Cinnamic acid (CA) is a precursor of many phenylpropanoid compounds, including catechins and aroma compounds, in tea (Camellia sinensis) leaves and is derived from L-phenylalanine (L-Phe) deamination. We have discovered an alternative CA formation pathway from L-Phe via phenylpyruvic acid (PPA) and phenyllactic acid (PAA) in tea leaves through stable isotope-labeled precursor tracing and enzyme reaction evidence. Both PPA reductase genes (CsPPARs) involved in the PPA-to-PAA pathway were isolated from tea leaves and functionally characterized in vitro and in vivo. CsPPAR1 and CsPPAR2 transformed PPA into PAA and were both localized in the leaf cell cytoplasm. Rosa hybrida flowers (economic crop flower), Lycopersicon esculentum Mill. fruits (economic crop fruit), and Arabidopsis thaliana leaves (leaf model plant) also contained this alternative CA formation pathway, suggesting that it occurred in most plants, regardless of different tissues and species. These results improve our understanding of CA biosynthesis in tea plants and other plants.
• Synthesis of13C6-labeled Reyataz? (BMS-232632)
  作者：Richard C. Burrell、Michael W. Lago、George M. Luke、J. Kent Rinehart

  DOI：10.1002/jlcr.905

  日期：2005.2

  An efficient synthesis of 13C6-labeled Reyataz™ (BMS-232632) is described. 13C6-labeled Reyataz™ was synthesized in eight steps from commercially available [ring-13C6]-L-phenylalanine. The overall yield of the synthesis was 8% and the purity of the final product was greater than 98%. Copyright © 2005 John Wiley & Sons, Ltd.

  描述了 13C6 标记的​​ Reyataz™ (BMS-232632) 的有效合成。13C6 标记的​​ Reyataz™ 是由市售的 [环-13C6]-L-苯丙氨酸分八步合成的。合成总收率为8%，最终产品纯度大于98%。版权所有 © 2005 John Wiley & Sons, Ltd.