Boc-Tyr(Boc)-Pro-OH | 345914-66-1

• 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: Boc-Tyr(Boc)-Pro-OH
• 英文别名: (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 345914-66-1
• 化学式: C₂₄H₃₄N₂O₈
• 分子量: 478.543
• InChiKey: KTOOTIJKBIMRGN-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  131.47
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Boc-Tyr(Boc)-Pro-OH 在 盐酸 、 溶剂黄146 作用下， 反应 0.75h， 生成 Tyr-Pro-OH hydrochloride
  参考文献：
  名称：

  Synthesis, pharmacokinetics, and metabolism of the C-terminal tripeptide of dermorphin and its diastereomer

  摘要：

  A tritium-labeled C-terminal fragment of dermorphin (H-Tyr-[3,4-H-3] Pro-Ser-NH2) and its isomer (H-Tyr-D-[3,4-H-3]Pro-Ser-NH2) with molar radioactivity of 35 Ci/mmol were synthesized, and their pharmacokinetics and metabolism in rat organs were studied after their intramuscular injections. The tripeptides were detected in the blood only for 5 min after the injection, and maximum contents of both compounds (approximately 5% of the total amount of the injected label) were registered in the kidneys after 20 min. Both stereomers were shown to penetrate into the brain. We failed to detect any radioactive metabolite, except proline, due to rapid proteolytic degradation of these peptides.

  DOI：

  10.1134/s1068162007060015
• 作为产物：
  描述：

  N,O-双[(叔丁氧基)羰基]-L-酪氨酸 、 L-脯氨酸 在 三甲基乙酰氯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.66h， 以95%的产率得到Boc-Tyr(Boc)-Pro-OH
  参考文献：
  名称：

  Synthesis, pharmacokinetics, and metabolism of the C-terminal tripeptide of dermorphin and its diastereomer

  摘要：

  A tritium-labeled C-terminal fragment of dermorphin (H-Tyr-[3,4-H-3] Pro-Ser-NH2) and its isomer (H-Tyr-D-[3,4-H-3]Pro-Ser-NH2) with molar radioactivity of 35 Ci/mmol were synthesized, and their pharmacokinetics and metabolism in rat organs were studied after their intramuscular injections. The tripeptides were detected in the blood only for 5 min after the injection, and maximum contents of both compounds (approximately 5% of the total amount of the injected label) were registered in the kidneys after 20 min. Both stereomers were shown to penetrate into the brain. We failed to detect any radioactive metabolite, except proline, due to rapid proteolytic degradation of these peptides.

  DOI：

  10.1134/s1068162007060015

文献信息

• Novel Ester-Linked Carbohydrate−Peptide Adducts: Effect of the Peptide Substituent on the Pathways of Intramolecular Reactions
  作者：Ivanka Jeric´、Štefica Horvat

  DOI：10.1002/1099-0690(200104)2001:8<1533::aid-ejoc1533>3.0.co;2-y

  日期：2001.4

  Carbohydrate−peptide conjugates in which D-glucose is linked through an ester linkage to the carboxy group of Tyr-Pro (2), Tyr-Pro-Phe (5) or Tyr-Pro-Phe-Val (11), through the C6 hydroxy group of the sugar moiety were synthesized to examine the utility of this type of monosaccharide modification for peptide prodrugs. Evidence is provided that glycoconjugates 2, 5, and 11 easily undergo intramolecular

  碳水化合物-肽缀合物，其中 D-葡萄糖通过酯键连接至 Tyr-Pro (2)、Tyr-Pro-Phe (5) 或 Tyr-Pro-Phe-Val (11) 的羧基，通过 C6合成糖部分的羟基以检查这种类型的单糖修饰对肽前药的效用。有证据表明，糖缀合物 2、5 和 11 容易发生分子内化学转化，随后攻击肽骨架上或 D-葡萄糖部分异头位置的游离 N 端氨基，导致二酮哌嗪的形成12、糖胺 13 或酮糖衍生物 15。数据表明肽链的长度和结构是控制所研究的碳水化合物-肽酯分子内反应的主要因素。