(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid | 156017-45-7

• 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)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid
• 英文别名: N-α-Fmoc-4-[diethylphosphono-(difluoromethyl)]-L-phenylalanine；N-Fmoc diethyl 4-phosphono(difluoromethyl)-L-phenylalanine；4-[(Dithylphosphono)difluoromethyl]-N-(fluoren-9-ylmethoxycarbonyl)-L-phenylalamine；(2S)-3-[4-[diethoxyphosphoryl(difluoro)methyl]phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 156017-45-7
• 化学式: C₂₉H₃₀F₂NO₇P
• 分子量: 573.53
• InChiKey: NSVBWEBDIJGLME-SANMLTNESA-N

物化性质

• 沸点：
  721.4±60.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 N-Α-FMOC-4-(膦酰基二氟甲基)-L-苯基丙氨酸
  参考文献：
  名称：

  Efficient Scaled-Up Synthesis of N-α-Fmoc-4-Phosphono(difluoromethyl)-l-phenylalanine and Its Incorporation into Peptides

  摘要：

  本文介绍了一种快速、稳健和高效的 N-α-Fmoc-4-phosphono(difluoromethyl)-l-phenylalanine 放大合成策略，以及将其直接掺入肽中的方法。

  DOI：

  10.1055/s-0030-1260206
• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 在 lithium hydroxide 、 copper(l) chloride 、 镉 作用下， 以 四氢呋喃 为溶剂， 反应 40.17h， 生成 (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid
  参考文献：
  名称：

  A facile solution and solid phase synthesis of phosphotyrosine mimetic l-4-[diethylphosphono(difluoromethyl)]-phenylalanine (F2Pmp(EtO)2) derivatives

  摘要：

  The F(2)Pmp derivatives were prepared in 80-90% yield from commercially available protected L-l-iodophenylalanine by esterification with diazomethane followed by a CuCl-mediated coupling to (diethylphosphonyl) difluoromethylcadmium bromide. Moreover, treatment of L-4-iodoPhe-containing peptides under the same coupling conditions provided the F,Pmp-containing peptides in very good yields. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00374-8

文献信息

• Ptb1b photoprobes
  申请人：Ramachandran Chidambaram

  公开号：US20070161542A1

  公开（公告）日：2007-07-12

  Photoaffinity probes (photoprobes) of the PTP1B enzyme contain the trifluoromethylphenyl diazirene photophore attached to compounds which bind to the PTP1B enzyme. The photoprobes bind irreversibly to the PTP1B enzyme upon irradiation, and can be used to study the binding of compounds to the PTP1B enzyme. Compounds that bind to the PTP1B enzyme may inhibit PTP1B and may be useful in the treatment of type 2 diabetes.

  PTP1B酶的光亲和探针（光探针）包含连接到与PTP1B酶结合的化合物的三氟甲基苯基重氮烷光团。在照射后，光探针不可逆地结合到PTP1B酶上，可用于研究化合物与PTP1B酶的结合。结合到PTP1B酶的化合物可能会抑制PTP1B，并可能在治疗2型糖尿病方面有用。
• [EN] DRUG-PHOSPHATE CONJUGATES AS PRODRUGS<br/>[FR] PROMEDICAMENTS CONTENANT DES CONJUGUES DE PHOSPHATE-MEDICAMENT ET DES ANALOGUES DE CEUX-CI
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2006037090A3

  公开（公告）日：2007-05-10
• Enantioselective synthesis of N-boc and N-fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine; agents suitable for the solid-phase synthesis of peptides containing nonhydrolyzable analogues of O-phosphotyrosine
  作者：Mark S. Smyth、Terrence R. Burke

  DOI：10.1016/s0040-4039(00)75835-7

  日期：1994.1

  Enantioselective convergent syntheses of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine are reported. le analogues of O-phosphotyrosine/
• An Efficient Synthesis of <i>N</i>-α-Fmoc-4-(Phosphonodifluoromethyl)-<scp>l</scp>- phenylalanine
  作者：Dennis Solas、Ron L. Hale、Dinesh V. Patel

  DOI：10.1021/jo9517508

  日期：1996.1.1
• Synthesis of a novel peptidic photoaffinity probe for the PTP-1B enzyme
  作者：Michel Thérien、Kathryn Skorey、Robert Zamboni、Chun Sing Li、Cheuk K Lau、Tammy LeRiche、Vouy Linh Truong、Deena Waddleton、Chidambaram Ramachandran

  DOI：10.1016/j.bmcl.2004.01.101

  日期：2004.5

  The synthesis of a novel radioactive peptidic photoaffinity probe for the PTP-1B enzyme as well as some SAR leading to the choice of this compound as a photoaffinity probe are presented. (C) 2004 Elsevier Ltd. All rights reserved.