(1R)-1-(L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid hydrochloride | 1158975-03-1

• 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: (1R)-1-(L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid hydrochloride
• 英文别名: [(1R)-1-[[(2S)-2-[[(2S)-2-amino-3-(4-methoxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutyl]boronic acid;hydrochloride
• CAS: 1158975-03-1
• 化学式: C₂₀H₃₄BN₃O₅*ClH
• 分子量: 443.779
• InChiKey: BGKOQCURHFZZDH-UVJOBNTFSA-N

物化性质

• 熔点：
  172-173 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  134
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,5S)-(+)-2,3-蒎烷二醇 、 (1R)-1-(L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid hydrochloride 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (S)-2-((S)-2-amino-3-(4-methoxyphenyl)propanamido)-3-methyl-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)butanamide hydrochloride
  参考文献：
  名称：

  Synthesis of boronic acid derivatives of tyropeptin: Proteasome inhibitors

  摘要：

  Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.117
• 作为产物：
  描述：

  在 盐酸 、 异丁基硼酸 、 水 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以33.3 mg的产率得到(1R)-1-(L-O-methyltyrosyl-L-valyl)amino-3-methyl-1-butylboronic acid hydrochloride
  参考文献：
  名称：

  Synthesis of boronic acid derivatives of tyropeptin: Proteasome inhibitors

  摘要：

  Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.117

文献信息

• Synthesis of boronic acid derivatives of tyropeptin: Proteasome inhibitors
  作者：Takumi Watanabe、Isao Momose、Masatoshi Abe、Hikaru Abe、Ryuichi Sawa、Yoji Umezawa、Daishiro Ikeda、Yoshikazu Takahashi、Yuzuru Akamatsu

  DOI：10.1016/j.bmcl.2009.02.117

  日期：2009.4

  Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro. (C) 2009 Elsevier Ltd. All rights reserved.