Boc-Phe-Phe-O^tBu

• 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-Phe-Phe-O^tBu
• 英文别名: tert-butyl (2S)-2-[[(2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoyl]amino]-3-phenyl-propanoate；tert-butyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoate
• 化学式: C₂₇H₃₆N₂O₅
• 分子量: 468.593
• InChiKey: PYBNARQJBYUMLN-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Phe-O^tBu 以 水 为溶剂， 250.0 ℃ 、1.03 MPa 条件下， 反应 0.17h， 以96%的产率得到(3S,6S)-3,6-双(苯甲基)-2,5-哌嗪二酮
  参考文献：
  名称：

  在水性介质中高效微波辅助合成 2,5-二酮哌嗪。

  摘要：

  在微波辐射下，N α-Boc-二肽基-叔丁基酯和甲酯的水原位一锅 N-Boc-脱保护-环化以优异的产率提供了 2,5-二酮哌嗪 (DKP)。该方案快速、安全、环保且高效，并表明叔丁氧基部分也是这些环化的极好离去基团。

  DOI：

  10.3390/molecules14082836
• 作为产物：
  描述：

  (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 在 5A molecular sieve 、 氯化锆(IV) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 Boc-Phe-Phe-O^tBu
  参考文献：
  名称：

  Efficient Transamidation of Primary Carboxamides by in Situ Activation with N,N-Dialkylformamide Dimethyl Acetals

  摘要：

  Two protocols for the transamidation of primary amides with primary and secondary amines, forming secondary and tertiary amides, respectively, are described. Both processes employ N,N-dialkylformamide dimethyl acetals for primary amide activation, producing N'-acyl-N,N-dialkylformamidines as intermediates, as widely documented in the literature. Although the latter intermediates react irreversibly with amines by amidinyl transfer, we show that in the presence of certain Lewis acid additives efficient acyl transfer occurs, providing new and useful methods for amide exchange. In one protocol for transamidation, the N'-acyl- N,N-dialkylformamidine intermediates are purified by flash-column chromatography and the purified intermediates are then treated with an amine (typically, 2.5 equiv) in the presence of scandium triflate (10 mol %) in ether to form in high yields the products of transamidation. In a second procedure, N'-acyl-N,N-dialkylformamidines are generated in situ and, without isolation, are subjected to transamidation in the presence of zirconium chloride (0.5 equiv) and an amine (typically 2 equiv). A variety of different primary amides and amines are found to undergo efficient transamidation using the methods described.

  DOI：

  10.1021/ja066728i

文献信息

• Deprotection of N-tert-butoxycarbonyl (Boc) groups in the presence of tert-butyl esters
  作者：Linus S Lin、Thomas Lanza、Stephen E de Laszlo、Quang Truong、Theodore Kamenecka、William K Hagmann

  DOI：10.1016/s0040-4039(00)01203-x

  日期：2000.9

  Deprotection of Boc groups in the presence of tert-butyl esters was achieved by using concentrated H2SO4 (1.5–3.0 equiv.) in tBuOAc or MeSO3H (1.5–3.0 equiv.) in tBuOAc:CH2Cl2 (4:1 v/v). The yields ranged from 70 to 100% for a variety of amino acid and dipeptide substrates.

  在叔丁酯存在下，通过在t BuOAc中使用浓H 2 SO 4（1.5–3.0当量）或在t BuOAc：CH 2 Cl 2中使用MeSO 3 H（1.5–3.0当量），实现Boc基团的脱保护。（4：1 v / v）。对于各种氨基酸和二肽底物，收率范围为70％至100％。
• Design criteria for minimalist mimics of protein–protein interface segments
  作者：Jaru Taechalertpaisarn、Rui-Liang Lyu、Maritess Arancillo、Chen-Ming Lin、Zhengyang Jiang、Lisa M. Perez、Thomas R. Ioerger、Kevin Burgess

  DOI：10.1039/c8ob02901f

  日期：——

  We present several critical design criteria of minimalist peptidomimetics deduced via extensive computational and data-mining studies on nine representative mimic designs.

  我们通过对九种代表性模拟设计进行广泛的计算和数据挖掘研究，提出了几个极简肽类模拟物的关键设计标准。
• Probing the self-assembly and anti-glioblastoma efficacy of a cinnamoyl-capped dipeptide hydrogelator
  作者：E. D. Sitsanidis、P. M. Kasapidou、J. R. Hiscock、V. Gubala、H. Castel、P. I. A. Popoola、A. J. Hall、A. A. Edwards

  DOI：10.1039/d2ob01339h

  日期：——

  Herein, we introduce the first diphenylalanine dipeptide hydrogelator capped with the cinnamoyl functional group (Cin-L-F-L-F). We evaluate the effects of the cinnamoyl moiety on molecular self-assembly events and resultant physical properties of the hydrogel formed. In addition, we report our preliminary results of this dipeptide's cytotoxicity against glioblastoma (GBM) cancer cells.

  在此，我们介绍了第一个用肉桂酰基官能团（Cin- L -F- L -F）封端的二苯丙氨酸二肽水凝胶剂。我们评估了肉桂酰基部分对分子自组装事件和所形成的水凝胶的物理性质的影响。此外，我们报告了这种二肽对胶质母细胞瘤 (GBM) 癌细胞的细胞毒性的初步结果。
• Triggering a transient organo-gelation system in a chemically active solvent
  作者：Romain Chevigny、Johanna Schirmer、Carmen C. Piras、Andreas Johansson、Elina Kalenius、David K. Smith、Mika Pettersson、Efstratios D. Sitsanidis、Maija Nissinen

  DOI：10.1039/d1cc04021a

  日期：——

  organo-gelation system with spatiotemporal dynamic properties is described. Here, the solvent actively controls a complex set of equilibria that underpin the dynamic assembly event. The observed metastability is due to the in situ formation of a secondary solvent, acting as an antagonist against the primary solvent of the organogel.

  描述了具有时空动态特性的瞬态有机凝胶系统。在这里，溶剂主动控制一组复杂的平衡，这些平衡是动态组装事件的基础。观察到的亚稳定性是由于次级溶剂的原位形成，作为有机凝胶主要溶剂的拮抗剂。
• Efficient Microwave Assisted Syntheses of 2,5-Diketopiperazines in Aqueous Media
  作者：Lemuel Pérez-Picaso、Jaime Escalante、Horacio Olivo、María Yolanda Rios

  DOI：10.3390/molecules14082836

  日期：——

  Aqueous in situ one-pot N-Boc-deprotection-cyclization of N alpha-Boc-dipeptidyl-tert-butyl and methyl esters under microwave irradiation afforded 2,5-diketopiperazines (DKPs) in excellent yields. This protocol is rapid, safe, environmentally friendly, and highly efficient, and showed that the tert-butoxy moiety is also an excellent leaving group for these cyclizations.

  在微波辐射下，N α-Boc-二肽基-叔丁基酯和甲酯的水原位一锅 N-Boc-脱保护-环化以优异的产率提供了 2,5-二酮哌嗪 (DKP)。该方案快速、安全、环保且高效，并表明叔丁氧基部分也是这些环化的极好离去基团。