(2S)-2-amino-3-(4-tert-butoxyphenyl)propan-1-ol | 176502-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-amino-3-(4-tert-butoxyphenyl)propan-1-ol
• 英文别名: O-tert-butyl-S-tyrosinol；H-L-tyrosinol(tBu)；O-tBu-L-tyrosinol；(S)-2-Amino-3-(4-(tert-butoxy)phenyl)propan-1-ol；(2S)-2-amino-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propan-1-ol
• CAS: 176502-70-8
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: WWWLEUYWIFWKQN-NSHDSACASA-N

物化性质

• 沸点：
  369.0±27.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-3-(4-tert-butoxyphenyl)propan-1-ol 在 copper(ll) sulfate pentahydrate 、 triflic azide 、 铜 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成 tert-butyl 4-((2S,3S)-2-(4-(4-(1-((S)-1-(4-(tert-butoxy)phenyl)-3-hydroxypropan-2-yl)-1H-1,2,3-triazol-4-yl)phenyl)-1H-1,2,3-triazol-1-yl)-3-methylpentanoyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Universal Peptidomimetics

  摘要：

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.

  DOI：

  10.1021/ja1071916
• 作为产物：
  描述：

  O-(叔丁基)-N-[(苯甲氧基)羰基]-L-酪氨酸 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -20.0 ℃ 、100.0 kPa 条件下， 反应 0.33h， 生成 (2S)-2-amino-3-(4-tert-butoxyphenyl)propan-1-ol
  参考文献：
  名称：

  N，N'-连接的脂肪族低聚脲及其相关杂化物的微波增强固相合成

  摘要：

  报道了一种实用，有效的微波辅助固相法，用于合成N，N'-连接的寡聚脲和相关的酰胺/脲杂化低聚物，其特征在于使用了琥珀酰亚胺基（2-叠氮基-2-取代的乙基）氨基甲酸酯单体。 。微波辐照下尿素形成的速率提高，以及基于膦的叠氮化物还原的温和条件，使得该方法对于常规合成寡聚尿素以及可能用于文库生产非常有效。

  DOI：

  10.1021/ol3012106

文献信息

• Synthesis and biological evaluation of leucine enkephalin turn mimetics
  作者：David Blomberg、Paul Kreye、Chris Fowler、Kay Brickmann、Jan Kihlberg

  DOI：10.1039/b515618a

  日期：——

  A cyclic Leu-enkephalin mimetic containing a 7-membered ring, and two linear analogues, has been prepared on solid phase. In the cyclic mimetic the intramolecular (1–4) hydrogen bond found in crystalline Leu-enkephalin has been replaced by an ethylene bridge. In addition, the amide bond between Tyr1 and Gly2 has been replaced by a methylene ether isostere and Gly3 has been deleted. The two linear analogues both contain the methylene ether isostere instead of the Tyr1-Gly2 amide bond and the shorter of the two lacks Gly3. The three compounds, and a β-turn mimetic analogous to the 7-membered turn mimetic but with Gly3 included, were evaluated for specific binding to μ- and δ-opioid receptors in rat brain membranes. With the exception of the β-turn mimetic the three other Leu-enkephalin analogues all bound with varying affinity to the μ- and δ-opioid receptors. From the results it could be concluded that Leu-enkephalin binds in a turn conformation to the opiate receptors, but that this conformation is not a (1–4) β-turn.

  一种含七元环的环状亮氨酸脑啡肽模拟物及两种线性类似物已通过固相合成制备。在环状模拟物中，结晶态亮氨酸脑啡肽中的分子内(1–4)氢键被乙烯桥取代。此外，酪氨酸1和甘氨酸2之间的酰胺键被甲撑醚同位素取代，且甘氨酸3被删除。两种线性类似物均含有甲撑醚同位素，而非酪氨酸1-甘氨酸2的酰胺键；其中较短者缺乏甘氨酸3。这三种化合物以及一种类似于七元环转折模拟物但包含甘氨酸3的β-转折模拟物，均在鼠脑膜中针对μ-和δ-阿片受体的特异性结合进行了评估。除β-转折模拟物外，其他三种亮氨酸脑啡肽类似物均以不同亲和力结合到μ-和δ-阿片受体。结果表明，亮氨酸脑啡肽以转折构象结合于阿片受体，但此构象并非(1–4)β-转折。
• Solid-Phase Synthesis of Tyrosine Peptide Aldehydes. Analogues of (<i>S</i>)-MAPI
  作者：Patrick Page、Mark Bradley、Iain Walters、Simon Teague

  DOI：10.1021/jo981546v

  日期：1999.2.1

  We report an efficient solid-phase synthesis of C-terminal tyrosine peptide aldehydes based on the HIV protease inhibitors (S)-MAPI and GE 20372 A. Our strategy consisted of anchoring the side chain of Dde-Tyrosinol (5) onto the brominated Wang linker derivative ((4-bromomethyl)-phenoxy-allyl acetate) (6) to give after ester hydrolysis the N(alpha)-(Dde)-O-(4-methylphenoxyacetic acid)-L-Tyrosinol template

  我们报告了基于HIV蛋白酶抑制剂（S）-MAPI和GE 20372 A的C末端酪氨酸肽醛的高效固相合成。我们的策略包括将Dde-酪氨酸（5）的侧链锚定到溴化Wang上接头衍生物（（4-溴甲基）-苯氧基-烯丙基乙酸酯）（6），在酯水解后得到Nα-（Dde）-O-（4-甲基苯氧基乙酸）-L-酪氨酸模板（8）。将其连接到氨基甲基树脂上，并使用标准Fmoc方案延长。重要的是，没有证据表明存在酯化副反应。使用Nα-（4-硝基苯氧基羰基）氨基酸叔丁基酯掺入（S）-MAPI族的不对称取代脲键，然后固定在固体支持物上的被保护的四肽醇被氧化成其相应的醛使用三氧化硫吡啶。通过在连接子和固体支持物之间引入一个小的PEG-间隔物，可以大大提高氧化步骤的效率和可靠性。通过酸解将四肽12a和12b裂解，通过RP HPLC纯化，并以高收率和纯度分离，证明了整个合成过程的成功。
• Acceleration of Mycobacterium growth
  申请人：ST GEORGE'S HOSPITAL MEDICAL SCHOOL

  公开号：US10633630B2

  公开（公告）日：2020-04-28

  The invention is in the field of growth of Mycobacteria. In particular, agents have been identified which enhance the growth of Mycobacterial species, which are naturally slow-growing. Such agents can therefore be used in the identification of Mycobacteria and in the diagnosis of Mycobacterial infections.

  本发明属于分枝杆菌生长领域。特别是，已经发现了能促进自然生长缓慢的分枝杆菌生长的制剂。因此，这些制剂可用于分枝杆菌的鉴定和分枝杆菌感染的诊断。
• Protein–Protein Interface Mimicry by an Oxazoline Piperidine-2,4-dione
  作者：Xun Li、Jaru Taechalertpaisarn、Dongyue Xin、Kevin Burgess

  DOI：10.1021/ol5036547

  日期：2015.2.6

  Representative minimalist mimics 1 were prepared from amino acids. Scaffold 1 was not designed to mimic any particular secondary structure, but simulated accessible conformations of this material were compared with common ideal secondary structures and with >125,000 different protein-protein interaction (PPI) interfaces. This data mining exercise indicates that scaffolds 1 can mimic features of sheet-turn-sheets, somewhat fewer helical motifs, and numerous PPI interface regions that do not resemble any particular secondary structure.
• Caplar, Vesna; Raza, Zlata; Katalenic, Darinka, Croatica Chemica Acta, 2003, vol. 76, # 1, p. 23 - 36
  作者：Caplar, Vesna、Raza, Zlata、Katalenic, Darinka、Zinic, Mladen

  DOI：——

  日期：——