(S)-N^α-tert-butyloxycarbonyl-O-benzyl-m-phenyltyrosine benzyl ester | 906356-31-8

• 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: (S)-N^α-tert-butyloxycarbonyl-O-benzyl-m-phenyltyrosine benzyl ester
• 英文别名: benzyl (S)-3-(6-(benzyloxy)-[1,1'-biphenyl]-3-yl)-2-(((benzyloxy)carbonyl)amino)propanoate；benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(3-phenyl-4-phenylmethoxyphenyl)propanoate
• CAS: 906356-31-8
• 化学式: C₃₄H₃₅NO₅
• 分子量: 537.656
• InChiKey: QPWRFBJKZDHOLY-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N^α-tert-butyloxycarbonyl-O-benzyl-m-phenyltyrosine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 以95%的产率得到(S)-N^α-tert-butyloxycarbonyl-m-phenyltyrosine
  参考文献：
  名称：

  Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives

  摘要：

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.

  DOI：

  10.1021/jo060704c
• 作为产物：
  描述：

  Boc-l-3-碘酪氨酸 在 palladium diacetate sodium carbonate 、 三(邻甲基苯基)磷 作用下， 以 乙二醇二甲醚 、 水 、 丙酮 为溶剂， 反应 5.0h， 生成 (S)-N^α-tert-butyloxycarbonyl-O-benzyl-m-phenyltyrosine benzyl ester
  参考文献：
  名称：

  Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives

  摘要：

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.

  DOI：

  10.1021/jo060704c

文献信息

• LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs
  作者：Evan Augustyn、Karissa Finke、Arik A. Zur、Logan Hansen、Nathan Heeren、Huan-Chieh Chien、Lawrence Lin、Kathleen M. Giacomini、Claire Colas、Avner Schlessinger、Allen A. Thomas

  DOI：10.1016/j.bmcl.2016.04.023

  日期：2016.6

  acid. Tyrosine and phenylalanine analogs substituted at the meta position with halogens, alkyl and aryl groups were synthesized and tested in cis-inhibition and trans-stimulation cell assays to determine activity. Contrary to our initial hypothesis we found that lipophilicity was correlated with diminished substrate activity and increased inhibition of the transporter. The synthesis and SAR of meta-substituted

  转运蛋白大中性氨基酸转运蛋白1（LAT-1，SLC7A5）负责转运氨基酸，例如酪氨酸和苯丙氨酸以及甲状腺激素，它已被用作药物输送机制。最近，人们越来越认识到它在癌症中的作用，因为已经发现它在许多不同的肿瘤类型中均被上调，并且其表达水平与预后相关。在meta处替换据报道，芳香氨基酸的位置增加了对LAT-1的亲和力；但是，此位置的SAR以前未曾探索过。在结合位点的最新精炼计算模型的指导下，我们假设能够填充疏水口袋的基团会增加与LAT-1的结合，从而相对于母体氨基酸改善了底物。合成了在间位被卤素，烷基和芳基取代的酪氨酸和苯丙氨酸类似物，并进行了顺式抑制和反式测试-刺激细胞测定以确定活性。与我们最初的假设相反，我们发现亲脂性与底物活性降低和转运蛋白抑制作用增加有关。描述了间位取代的苯丙氨酸和酪氨酸类似物的合成和SAR 。
• Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives
  作者：Sebastian Knör、Burkhardt Laufer、Horst Kessler

  DOI：10.1021/jo060704c

  日期：2006.7.1

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.