H-3,5-diiodo-Tyr-Gly-Gly-Phe-Met-OH | 78269-62-2

• 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: H-3,5-diiodo-Tyr-Gly-Gly-Phe-Met-OH
• CAS: 78269-62-2
• 化学式: C₂₇H₃₃I₂N₅O₇S
• 分子量: 825.463
• InChiKey: IYVBBKNSZHPSMH-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  199.95
• 氢给体数：
  7.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  potassium (2,4-difluorophenyl)trifluoroborate 、 H-3,5-diiodo-Tyr-Gly-Gly-Phe-Met-OH 在 potassium phosphate 、 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 作用下， 以 水 为溶剂， 反应 24.0h， 生成 、 (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-[3,5-bis(2,4-difluorophenyl)-4-hydroxyphenyl]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
  参考文献：
  名称：

  Arylation of Phe and Tyr Side Chains of Unprotected Peptides by a Suzuki−Miyaura Reaction in Water

  摘要：

  An efficient arylation in water of tyrosine and phenylalanine side chains from unprotected iodopeptides is accomplished by using Suzuki-Miyaura cross-coupling processes. The method is compatible with the hydrophilic and thermolabile nature of biologically active peptides. Also of interest, the arylated tyrosine peptides can be accessed in one-pot mode starting from native peptides.

  DOI：

  10.1021/ol801009z
• 作为产物：
  描述：

  (S)-2-[(S)-2-(2-{2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid 生成 H-3,5-diiodo-Tyr-Gly-Gly-Phe-Met-OH
  参考文献：
  名称：

  First aromatic electrophilic iodination reaction on the solid-phase: Iodination of bioactive peptides

  摘要：

  Direct iodination of Tyr residues of peptides anchored on solid supports was accomplished, for the first time, by aromatic electrophilic attack of iodonium ions provided by the IPy2BF4 reagent. Compatibility studies of the iodination with routine solid-phase synthesis protocols are reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01604-9