O-[二(苄氧基)磷酰]-N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸 | 92265-01-5

• 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: O-[二(苄氧基)磷酰]-N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸
• 英文名称: Boc-Tyr(PO3Bzl2)-OH
• 英文别名: (2S)-3-[4-bis(phenylmethoxy)phosphoryloxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 92265-01-5
• 化学式: C₂₈H₃₂NO₈P
• mdl: MFCD00080285
• 分子量: 541.538
• InChiKey: ZZQAAAGYMATKRJ-VWLOTQADSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  674.5±55.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O-[二(苄氧基)磷酰]-N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [1-[5-(3-cyclohexyl-propyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylcarbamoyl]-2-(4-phosphonooxy-phenyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of Thioazepinone Ligands for Src SH2: From Non-specific to Specific Binding

  摘要：

  The structure-based design and synthesis of new thioazepinones as ligands for Src SH2 protein is presented. From benzothioazepinones, ligands with somewhat unspecific binding properties, simpler thioazepinones were designed, the best ones demonstrated nanomolar affinity for Src SH2. A few of these new ligands were crystallized with the protein and demonstrated a specific binding mode with the protein. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00386-9
• 作为产物：
  描述：

  亚磷酸二苄酯 在 四氯化碳 、 sodium dithionite 、 sodium carbonate 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.0h， 生成 O-[二(苄氧基)磷酰]-N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸
  参考文献：
  名称：

  两种合成磷酸酪氨酸肽的液体二次电离质谱表征

  摘要：

  合成这些 en phase solide etude des schemas de fragmentation de Val-X-Phe et de Arg-X-Val-Phe (X=O-phosphonotyrosyl)

  DOI：

  10.1021/ja00252a007

文献信息

• An Improved One-pot Synthesis of<i>N</i> ^α-(<i>tert</i>-Butoxycarbonyl)-<i>O</i>-(<i>O</i>′,<i>O</i>″-dialkylphosphoro)-L-tyrosines Using Dialkyl<i>N,N</i>-Diethylphosphoramidites
  作者：John W. Perich、R. B. Johns

  DOI：10.1055/s-1989-27366

  日期：——

  N α-(tert-Butoxycarbonyl)-O-(O′,O″-dialkylphosphoro)-L-tyrosines 6a-c were prepared in high yields by an efficient one-pot procedure, which involved initial tert-butyldimethylsilyl protection of the carboxy terminus of N-Boc tyrosine 1 followed by successive in situ phosphitylation of the tyrosyl hydroxyl group, oxidation of the resultant phosphite triester and deprotection.

  N δ-（叔丁氧基羰基）-O-（O′,O″-二烷基磷）-L-酪氨酸 6a-c 是通过高效的一锅法高产率制备的，该方法包括对 N-Boc 酪氨酸 1 的羧基末端进行叔丁基二甲基硅基保护，然后对酪氨酸羟基进行连续的原位磷酸化，氧化生成的亚磷酸三酯并脱保护。
• Discovery of Potent and Selective SH2 Inhibitors of the Tyrosine Kinase ZAP-70
  作者：Chi B. Vu、Evelyn G. Corpuz、Taylor J. Merry、Selvaluxmi G. Pradeepan、Catherine Bartlett、Regine S. Bohacek、Martyn C. Botfield、Charles J. Eyermann、Berkley A. Lynch、Ian A. MacNeil、Mary K. Ram、Marie Rose van Schravendijk、Shelia Violette、Tomi K. Sawyer

  DOI：10.1021/jm990229t

  日期：1999.10.1

  A series of 1,2,4-oxadiazole analogues has been shown to be potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70, a potential therapeutic target for immune suppression. These compounds typically are 200-400-fold more potent than the native, monophosphorylated tetrapeptide sequences. When compared with the high-affinity xi-1-ITAM peptide (Ac-NQL-pYNELNLGRREE-pYDVLD-NH2, wherein pY refers to phosphotyrosine) some of the best 1,2,4-oxadiazole analogues are approximately 1 order of magnitude less active. This series of compounds displays an unprecedented level of selectivity over the closely related tyrosine kinase Syk, as well as other SH2-containing proteins such as Src and Grb2. Gel shift studies using a protein construct consisting only of C-terminal ZAP-70 SH2 demonstrate that these compounds can effectively engage this particular SH2 domain.
• Structure-based design and synthesis of a novel class of Src SH2 inhibitors
  作者：John L. Buchanan、Regine S. Bohacek、George P. Luke、Marcos Hatada、Xiaode Lu、David C. Dalgarno、Surinder S. Narula、Ruth Yuan、Dennis A. Holt

  DOI：10.1016/s0960-894x(99)00388-1

  日期：1999.8

  The structure-based design and synthesis of a novel class of 2,4-disubstituted thiazoles as Src SH2 inhibitors is described. Initial results are presented, including the X-ray and NMR analysis of one thiazole inhibitor bound to Lck and Src SH2. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of O-phosphotyrosine-containing peptides. 1. Synthesis of PTyr-Leu-Gly via benzyl phosphate protection
  作者：John W. Perich、R. B. Johns

  DOI：10.1021/jo00268a047

  日期：1989.3
• Synthesis of protected derivatives of O-phosphotyrosine incorporation in a heptapeptide
  作者：R.M. Valerio、P.F. Alewood、R.B. Johns、B.E. Kemp

  DOI：10.1016/s0040-4039(01)81243-0

  日期：1984.1