N^α-Fmoc-Tyr-OPfp | 105751-14-2

• 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: N^α-Fmoc-Tyr-OPfp
• 英文别名: Fmoc-Tyr-OPfp；Fmoc-Tyr-Pfp；Fmoc-Tyr(tBu)-OPfp；F-moc-Tyr-OPfp；(2,3,4,5,6-pentafluorophenyl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate
• CAS: 105751-14-2
• 化学式: C₃₀H₂₀F₅NO₅
• 分子量: 569.485
• InChiKey: WZHWQKBOBWITJZ-QFIPXVFZSA-N

物化性质

• 熔点：
  152-156 °C
• 沸点：
  719.4±60.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N^α-Fmoc-Tyr-OPfp 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 H-Tyr-(β-D-Glc)-Gly-Ala-NH2
  参考文献：
  名称：

  Convenient high yield and stereoselective synthesis of O -glycopeptides using N -α-Fmoc-Tyr/Ser[β- d -Glc(OAc) 4 ]OPfp generated in solution

  摘要：

  Fmoc-AA-OPfp (AA = Tyr or Ser) (1 equiv) was reacted with beta-D-Glc(OAc)(5) (6 equiv) in the presence of BF3.Et2O (6 equiv) in CH2Cl2 at room temperature for 2 h, and the glycosylation reaction mixture was used directly to couple to the amino group of the peptide resin without isolation and purification of the Fmoc-AA[beta-D-Glc(OAc)(4)]-OPfp. Moreover, the -OAc protecting groups of glucose was removed just prior to releasing the peptide from the resin using 6 mM NaOMe in 85% DMF-MeOH. The crude product obtained by TEA cleavage contained >90%, of the target O-glycopeptide, and the 500 MHz H-1 NMR analysis revealed that the glycosylation reaction was nearly stereoselective (>97% beta-anomer). This method is rapid and stereoselective, and can now be exploited for the routine synthesis of O-glycopeptides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.178
• 作为产物：
  描述：

  芴甲氧羰基-O-叔丁基-L-酪氨酸五氟苯酯 在 三氟乙酸 作用下， 反应 1.0h， 以94%的产率得到N^α-Fmoc-Tyr-OPfp
  参考文献：
  名称：

  Jensen, Knud J.; Meldal, Morten; Bock, Klaus, Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 2119 - 2130

  摘要：

  DOI：

文献信息

• Azido Acids in a Novel Method of Solid-Phase Peptide Synthesis.
  作者：Morten Meldal*、Maria A Juliano、Anita M Jansson

  DOI：10.1016/s0040-4039(97)00393-6

  日期：1997.4

  in a novel method of solid-phase synthesis. The azido acids were transformed into the highly activated acid chlorides and used synthesis of extremely hindered peptides containing up to four successive diphenyl glycine or Aib residues. By reaction of the genetically encoded amino acids with TfN3 and then SOCl2 they were transformed into α-azido acid chlorides used in solid-phase peptide synthesis without

  通过用NBS进行α-溴化，然后用叠氮化钠取代，由α-支链酸生产出叠氮酸，并将其用于新的固相合成方法。叠氮基酸被转化为高度活化的酰氯，并用于合成高度受阻的肽，该肽包含多达四个连续的二苯基甘氨酸或Aib残基。通过遗传编码的氨基酸与TfN 3然后与SOCl 2的反应，它们被转化为用于固相肽合成的α-叠氮酰氯，而没有消旋作用。©1997爱思唯尔科学有限公司。
• β-Galactosidase instructed supramolecular hydrogelation for selective identification and removal of senescent cells
  作者：Tengyan Xu、Yanbin Cai、Xinglong Zhong、Le Zhang、Debing Zheng、Zhengfeng Gao、Xianmei Pan、Fuqiang Wang、Minsheng Chen、Zhimou Yang

  DOI：10.1039/c9cc03056e

  日期：——

  We introduced a novel strategy of β-galactosidase instructed supramolecular hydrogelation for selective identification and removal of senescent cells.

  我们引入了一种新颖的β-半乳糖苷酶指导的超分子水凝胶化策略，用于选择性识别和去除衰老细胞。
• Compounds for Control of Appetite
  申请人：Balasubramaniam Ambikaipakan

  公开号：US20080221038A1

  公开（公告）日：2008-09-11

  This invention relates generally to peptides including tripeptides and to methods for pharmaceutical treatment of mammals using such tripeptides and analogs thereof. More specifically, the invention is directed to neuropeptide Y (“NPY”) receptor antagonists and agonists including O-glycosylated tripeptides, i.e. O-glycopeptides, and extended tripeptides, and their analogs, as well as to PYY analogs, to pharmaceutical compositions containing such tripeptides and PYY analogs, and to methods of treatment of mammals using such tripeptides and PYY analogs. In addition, the invention relates to methods of treatment of mammals using such tripeptides and PYY analogs for control of appetite, blood pressure, cardiovascular response, libido, and circadian rhythm.

  这项发明涉及一般的肽包括三肽以及使用这些三肽及其类似物对哺乳动物进行药物治疗的方法。更具体地，该发明涉及神经肽Y（“NPY”）受体拮抗剂和激动剂，包括O-糖基化三肽，即O-糖肽，以及扩展三肽及其类似物，以及PYY类似物，包括含有这些三肽和PYY类似物的药物组合物，以及使用这些三肽和PYY类似物对哺乳动物进行治疗的方法。此外，该发明涉及使用这些三肽和PYY类似物进行治疗的方法，用于控制食欲、血压、心血管反应、性欲和昼夜节律。
• Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase
  作者：Christina R. Tysoe、Sami Caner、Matthew B. Calvert、Anna Win-Mason、Gary D. Brayer、Stephen G. Withers

  DOI：10.1039/c9sc02610j

  日期：——

  Simplified analogues of the potent human amylase inhibitor montbretin A were synthesised and shown to bind tightly, K I = 60 and 70 nM, with improved specificity over medically relevant glycosidases, making them promising candidates for controlling blood glucose. Crystallographic analysis confirmed similar binding modes and identified new active site interactions.

  合成了强效人类淀粉酶抑制剂 montbretin A 的简化类似物，并显示其紧密结合，KI = 60 和 70 nM，与医学相关糖苷酶相比具有更高的特异性，使它们成为控制血糖的有希望的候选者。晶体学分析证实了相似的结合模式并确定了新的活性位点相互作用。
• Schoen, Istvan; Kisfaludy, Lajos, Synthesis, 1986, # 4, p. 303 - 305
  作者：Schoen, Istvan、Kisfaludy, Lajos

  DOI：——

  日期：——