[2-(13)C]-(S)-N5-(2',2',4',6',7'-pentamethyldihydrobenzofuran-5'-sulfonyl)arginine | 1196979-98-2

• 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: [2-(13)C]-(S)-N5-(2',2',4',6',7'-pentamethyldihydrobenzofuran-5'-sulfonyl)arginine
• 英文别名: (2S)-2-amino-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino](213C)pentanoic acid
• CAS: 1196979-98-2
• 化学式: C₁₉H₃₀N₄O₅S
• 分子量: 427.526
• InChiKey: GVIXTVCDNCXXSH-AKPJGTCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [2-(13)C]-(S)-N5-(2',2',4',6',7'-pentamethyldihydrobenzofuran-5'-sulfonyl)arginine 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 sodium carbonate 、 柠檬酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以75%的产率得到[2-(13)C]-(S)-N2-(9'-fluorenylmethoxycarbonyl)-N5-(2'',2'',4'',6'',7''-pentamethyldihydrobenzofuran-5''-sulfonyl)arginine
  参考文献：
  名称：

  Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃

  摘要：

  Enantioselective syntheses of selectively labeled, orthogonally protected [2-C-13]L-arginine and [1,3-C-13(2)]-L-proline are described from the commercially available precursors [2-C-13]bromoacetic acid and potassium [C-13]cyanide, Interestingly the enhanced signal assigned to C-2 in the C-13 NMR spectrum of alpha-Fmoc-Pbf-[2-C-13]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-C-13]-Arg9 and [1,3-C-13(2)]-Pro 10 labeled ligand (NT8-13) by manual Fmoc-SPSS.

  DOI：

  10.1021/jo9014497
• 作为产物：
  描述：

  [3-(13)C]-(3S,5S,6R)-4-benzyloxycarbonyl-5,6-diphenyl-3-(3'-hydroxyprop-1'-yl)morpholin-2-one 、 N,N'-di(benzyloxycarbonyl)-N''-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-ylsulfonyl)guanidine 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 80.0 ℃ 、344.75 kPa 条件下， 以0.58 g的产率得到[2-(13)C]-(S)-N5-(2',2',4',6',7'-pentamethyldihydrobenzofuran-5'-sulfonyl)arginine
  参考文献：
  名称：

  Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃

  摘要：

  Enantioselective syntheses of selectively labeled, orthogonally protected [2-C-13]L-arginine and [1,3-C-13(2)]-L-proline are described from the commercially available precursors [2-C-13]bromoacetic acid and potassium [C-13]cyanide, Interestingly the enhanced signal assigned to C-2 in the C-13 NMR spectrum of alpha-Fmoc-Pbf-[2-C-13]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-C-13]-Arg9 and [1,3-C-13(2)]-Pro 10 labeled ligand (NT8-13) by manual Fmoc-SPSS.

  DOI：

  10.1021/jo9014497

文献信息

• Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-<scp>l</scp>-arginine and Fmoc-[1,3-¹³C₂]-<scp>l</scp>-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃
  作者：Chuanjun Song、Satita Tapaneeyakorn、Annabel C. Murphy、Craig Butts、Anthony Watts、Christine L. Willis

  DOI：10.1021/jo9014497

  日期：2009.12.4

  Enantioselective syntheses of selectively labeled, orthogonally protected [2-C-13]L-arginine and [1,3-C-13(2)]-L-proline are described from the commercially available precursors [2-C-13]bromoacetic acid and potassium [C-13]cyanide, Interestingly the enhanced signal assigned to C-2 in the C-13 NMR spectrum of alpha-Fmoc-Pbf-[2-C-13]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-C-13]-Arg9 and [1,3-C-13(2)]-Pro 10 labeled ligand (NT8-13) by manual Fmoc-SPSS.