(S)-3-(3-bromo-4-methoxyphenyl)-2-((N-tert-butoxycarbonyl)-(methyl)amino)propanoic acid | 1260112-34-2

• 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: (S)-3-(3-bromo-4-methoxyphenyl)-2-((N-tert-butoxycarbonyl)-(methyl)amino)propanoic acid
• 英文别名: (S)-3-(3-bromo-4-methoxyphenyl)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid；Boc-mTyr(3-Br,4-OMe)-OH；N-Boc-N,O-dimethyl-3-bromotyrosine；(2S)-3-(3-bromo-4-methoxyphenyl)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid
• CAS: 1260112-34-2
• 化学式: C₁₆H₂₂BrNO₅
• 分子量: 388.258
• InChiKey: LPHJOPIEIPBVJS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(3-bromo-4-methoxyphenyl)-2-((N-tert-butoxycarbonyl)-(methyl)amino)propanoic acid 、 purpurealidin E 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到(N-tert-butoxycarbonyl)-iso-anomoian A
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B

  摘要：

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

  DOI：

  10.1021/np300102z
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-3-bromo-O-methyl-(S)-tyrosine methyl ester 在 水 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (S)-3-(3-bromo-4-methoxyphenyl)-2-((N-tert-butoxycarbonyl)-(methyl)amino)propanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B

  摘要：

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

  DOI：

  10.1021/np300102z

文献信息

• Development of a Solid-Phase Approach to the Natural Product Class of Ahp-Containing Cyclodepsipeptides
  作者：Sara C. Stolze、Michael Meltzer、Michael Ehrmann、Markus Kaiser

  DOI：10.1002/ejoc.201101757

  日期：2012.3

  overcome this limitation, we report a solid-phase approach to Ahp cyclodepsipeptides that is based on the use of a maskedglutamic aldehyde moiety as a general Ahp precursor molecule. As a proof-of-concept, we therefore recently reported the solid-phase synthesis of Symplocamide A. Here, we want to give a full account on the development and application of the masked glutamic aldehyde moiety as well as

  含有环缩肽的 3-氨基-6-羟基-2-哌啶酮 (Ahp) 是一类有趣的天然产物，它以可逆、非共价的方式抑制 S1（胰蛋白酶和糜蛋白酶样）丝氨酸蛋白酶，将它们变成潜在的化学工具，用于蛋白酶研究。然而，它们在化学生物学中的系统应用受到它们繁琐的液相化学合成的阻碍。为了克服这一限制，我们报告了一种 Ahp 环缩肽的固相方法，该方法基于使用掩蔽谷氨酸部分作为一般 Ahp 前体分子。因此，作为概念验证，我们最近报道了 Symplocamide A 的固相合成。在这里，我们想全面介绍掩蔽谷氨酸部分的开发和应用以及固相的优化。相合成，
• Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A
  作者：Sara C. Stolze、Michael Meltzer、Michael Ehrmann、Markus Kaiser

  DOI：10.1039/c0cc02889d

  日期：——

  The solid phase total synthesis of the marine cyanobacterial Ahp-cyclodepsipeptide Symplocamide A is reported as a model for a general route for the synthesis of tailor-made non-covalent serine protease inhibitors.

  据报道，海洋蓝细菌Ahp-环二肽Symplocamide A的固相全合成是定制非共价丝氨酸蛋白酶抑制剂合成一般路线的模型。