L-苯丙氨酸-15N | 29700-34-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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: L-苯丙氨酸-15N
• 中文别名: L-苯基丙氨酸-15N
• 英文名称: <¹⁵N>-L-phenylalanine
• 英文别名: <(15)N>-L-phenylalanine；L-<15N>-phenylalanine；L-<15N>phenylalanine；[(15)N]-α-phenylalanine；L-phenylalanine；phenylalanine；L-Phenylalanine-15N；(2S)-2-(15N)azanyl-3-phenylpropanoic acid
• CAS: 29700-34-3
• 化学式: C₉H₁₁NO₂
• 分子量: 166.185
• InChiKey: COLNVLDHVKWLRT-YTRLMEAHSA-N

物化性质

• 熔点：
  270-275 °C (dec.) (lit.)
• 溶解度：
  超声处理可轻微溶于甲醇和水

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

安全信息

• WGK Germany：
  3
• 海关编码：
  28459000

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸-15N 在 Pantoea agglomerans phenylalanine aminomutase 、 trans-cinnamic acid-β,2,3,4,5,6-d6 作用下， 生成
  参考文献：
  名称：

  Stereochemistry and Mechanism of a Microbial Phenylalanine Aminomutase

  摘要：

  The stereochemistry of a phenylalanine aminomutase (PAM) on the andrimid biosynthetic pathway in Pantoea agglomerans (Pa) is reported. PaPAM is a member of the 4-methylidene-1H-imidazol-5(4H)-one (MIO)-dependent family of catalysts and isomerizes (2S)-alpha-phenylalanine to (3S)-beta-phenylalanine, which is the enantiomer of the product made by the mechanistically similar aminomutase TcPAM from Taxus plants. The NH2 and pro-(3S) hydrogen groups at C-alpha and C-beta, respectively, of the substrate are removed and interchanged completely intramolecularly with inversion of configuration at the migration centers to form P-phenylalanine. This is a contrast to the retention of configuration mechanism followed by TcPAM.

  DOI：

  10.1021/ja2030728
• 作为产物：
  描述：

  (2S,2'S)-N-<2'-<15N>amino-3'-phenylpropanoyl>bornane-10,2-sultam 在 盐酸 、 lithium hydroxide 、 水 作用下， 生成 L-苯丙氨酸-15N
  参考文献：
  名称：

  Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L-[15N]alanine, L-[15N]valine, L-[15N]leucine, L-[15N]phenylalanine and L-[1-13C, 15N]valine

  摘要：

  Using 1-chloro-1-[N-15]nitrosocyclohexane, we have prepared five L-[alpha-N-15]amino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-10,2-sultams, followed by Zn-o/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5% e.e. By starting with labeled (S)-acylbornane-10,2-sultams this stereoselective route could be to prepare many C-13 and/or N-15 isotopomers of alpha-amino acids.

  DOI：

  10.1002/(sici)1099-1344(199603)38:3<239::aid-jlcr831>3.0.co;2-e

文献信息

• Achieving Reversible H₂/H⁺ Interconversion at Room Temperature with Enzyme-Inspired Molecular Complexes: A Mechanistic Study
  作者：Nilusha Priyadarshani、Arnab Dutta、Bojana Ginovska、Garry W. Buchko、Molly O’Hagan、Simone Raugei、Wendy J. Shaw

  DOI：10.1021/acscatal.6b01433

  日期：2016.9.2

  is observed in aqueous, acidic methanol. The aromatic rings in the peripheral phenylalanine groups appear to be essential to achieving reversibility based on the observation that reversibility for arginine (CyArg) or glycine (CyGly) complexes is only achieved with elevated temperature (>50 °C) in 100% water. A complex with a hydroxyl group in the para-position of the aromatic ring, R′ = tyrosine (CyTyr)

  受蛋白质支架对酶功能效率的贡献的启发，我们利用外配体特征开发了一种分子电催化剂，用于在25°C时可逆地产生/氧化H 2：[Ni（P Cy 2 N Phe 2）2 ] 2+（CyPhe，P - [R 2 ñ - [R ' 2＝ 1，5-二氮杂3，7-二磷酸环辛烷，Cy ＝环己基，Phe ＝苯丙氨酸）。在含水的酸性甲醇中观察到电催化可逆性。基于观察到精氨酸（CyArg）或甘氨酸（CyGly）配合物的可逆性只有在100％的水中升高温度（> 50°C）时才能实现，外围苯丙氨酸基团中的芳环似乎对于实现可逆性至关重要。芳香环对位带有羟基的络合物，R'=酪氨酸（CyTyr），显示出类似的可逆行为。NMR光谱学和分子动力学研究表明，芳族基团之间以及羧酸基团之间的相互作用限制了构象柔韧性，有助于可逆性。NMR光谱研究还显示，从Ni–H穿过侧链胺到羧基，质子交换非常快。此外，含有类似于酪氨酸但不带有羧基的侧链的复合物（CyTym;
• Oxidative Trimerization of Amino Acids: Selective Synthesis of 2,3,5-Trisubstituted Pyridines
  作者：Jia-Chen Xiang、Yan Cheng、Zi-Xuan Wang、Jin-Tian Ma、Miao Wang、Bo-Cheng Tang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.7b01232

  日期：2017.6.2

  An oxidative trimerization of three amino acids has been realized to furnish 2,3,5-trisubstuitued pyridines in both cross- and homo-trimerization types. This method is capable of converting simple linear biomass material to heterocycles, which features in the assembly of three amino acid branched chains into one aromatic ring. Molecular iodine triggers the sequential decarboxylation and deamination

  已经实现了三个氨基酸的氧化三聚，以提供交叉和均三聚类型的2,3,5-三取代的吡啶。该方法能够将简单的线性生物质材料转化为杂环，其特征在于将三个氨基酸支链组装成一个芳香环。分子碘触发氨基酸的顺序脱羧和脱氨基，然后促进新的C–N和C–C键的选择性形成。
• Hyperpolarization of Nitrogen‐15 Schiff Bases by Reversible Exchange Catalysis with <i>para</i> ‐Hydrogen
  作者：Angus W. J. Logan、Thomas Theis、Johannes F. P. Colell、Warren S. Warren、Steven J. Malcolmson

  DOI：10.1002/chem.201602393

  日期：2016.7.25

  NMR with thermal polarization requires relatively concentrated samples, particularly for nuclei with low abundance and low gyromagnetic ratios, such as 15N. We expand the substrate scope of SABRE, a recently introduced hyperpolarization method, to allow access to 15N‐enriched Schiff bases. These substrates show fractional 15N polarization levels of up to 2 % while having only minimal 1H enhancements

  具有热极化的NMR需要相对集中的样品，尤其是对于低丰度和低旋磁比（例如15 N）的原子核。我们扩大了SABRE的底物范围（一种最新引入的超极化方法），可以访问15种富N的席夫碱。这些基板显示出高达2％的分数15 N极化水平，而仅具有最小的1 H增强。
• Chemo-enzymatic syntheses of isotopically labelled L-amino acids
  作者：Nicholas M. Kelly、Bridget C. O'Neill、John Probert、Gordon Reid、Rosamund Stephen、Ting Wang、Christine L. Willis、Peter Winton

  DOI：10.1016/s0040-4039(00)78265-7

  日期：1994.8

  L-Alanine labelled with carbon-13 and nitrogen-15 has been prepared in good yield and high optical purity from achiral precursors using alanine dehydrogenase This versatile approach may be simply adapted for the preparation of a range of isotopically labelled amino acids and efficient syntheses of [15N]-labelled serine, valine, leucine and phenylalanine are described.

  使用丙氨酸脱氢酶从非手性前体中以高收率和高光学纯度制备了用碳13和氮15标记的L-丙氨酸。描述了[ 15 N]标记的丝氨酸，缬氨酸，亮氨酸和苯丙氨酸。
• Biosynthetic incorporation of cyclo-(L-phenylalanyl-L-phenylalanyl) into bisdethiobis(methylthio)acetylaranotin in Aspergillus terreus
  作者：Maria I. Pita Boente、Gordon W. Kirby、David J. Robins

  DOI：10.1039/c39810000619

  日期：——

  cyclo-(L-[15N] Phenylalanyl-L-[1-13C] phenylalanyl) was incorporated intact into bisdethiobis (methyl-thio) acetylaranotin (1) in Aspergillus terreus, the presence of doubly labelled species in the product being detected by 13C n.m.r. spectroscopy (JCN 13 Hz)

  环- （大号- [ 15 N]苯丙大号- [1- 13 acetylaranotin（C]苯丙）掺入完整地进入bisdethiobis（甲基-硫代）1）在土曲霉，被检测双标记的物种的在产品中的存在通过13 C nmr光谱法（J CN 13 Hz）