(R)-boroleucine hydrochloride | 1158974-93-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (R)-boroleucine hydrochloride
• 英文别名: (R)-(1-amino-3-methylbutyl)boronic acid hydrochloride；(R)-(1-Amino-3-methylbutyl)boronic acid hydrochloride；[(1R)-1-amino-3-methylbutyl]boronic acid;hydrochloride
• CAS: 1158974-93-6
• 化学式: C₅H₁₄BNO₂*ClH
• 分子量: 167.444
• InChiKey: VQKLOKXMTRTPCX-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-boroleucine hydrochloride 、 1-naphthylacetyl-Tyr(Me)-Val-OH 在 氰基磷酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1R)-1-[N-(1-naphthylacetyl)-L-O-methyltyrosyl-L-valyl]amino-3-methyl-1-butylboronic acid
  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：

  (aR,3aS,4S,6S,7aR)-六氢-3a,8,8-三甲基-alpha-(2-甲基丙基)-4,6-甲桥-1,3,2-苯并二氧硼烷-2-甲胺 2,2,2-三氟乙酸盐 在 盐酸 、 异丁基硼酸 、 水 作用下， 以 正己烷 为溶剂， 生成 (R)-boroleucine 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

• Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids
  作者：Stefan P. A. Hinkes、Christian D. P. Klein

  DOI：10.1021/acs.orglett.9b00584

  日期：2019.5.3

  Boronic acids are an increasingly important compound class for many applications, including C–C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and

  硼酸对于许多应用而言，都是越来越重要的化合物类别，包括C–C键形成反应，药物化学和诊断学。硼酸酯中间体的脱保护在硼酸合成中通常是一个有问题且效率低下的步骤。我们描述了一种通过利用甲基硼酸及其二醇酯的挥发性极大地促进这种转变的方法。该方法在温和条件下进行，提供了高收率，并且消除了繁琐且麻烦的纯化步骤。
• A solid-phase approach for the synthesis of α-aminoboronic acid peptides
  作者：Blake E. Daniels、Craig E. Stivala

  DOI：10.1039/c7ra13479g

  日期：——

  A solid-phase synthesis of α-aminoboronic acid peptides using a 1-glycerol polystyrene resin is described. Standard Fmoc solid-phase peptide chemistry is carried out to construct bortezomib and ixazomib. This approach eliminates the need for liquid–liquid extractions, silica gel column chromatography, and HPLC purifications, as products are isolated in high purity after direct cleavage from the resin

  描述了使用 1-甘油聚苯乙烯树脂固相合成 α-氨基硼酸肽。进行标准 Fmoc 固相肽化学以构建硼替佐米和 ixazomib。这种方法无需液-液萃取、硅胶柱色谱和 HPLC 纯化，因为产品在从树脂中直接裂解后以高纯度分离。
• 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.