cyclo(Ala-Phe) | 15180-22-0

• 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: cyclo(Ala-Phe)
• 英文别名: cyclo(L-Phe-L-Ala)；cyclo(Phe-Ala)；Cyclo-L-Ala-L-Phe；cyclo-L-alanyl-L-phenylalanyl；(3S,6S)-3-benzyl-6-methylpiperazine-2,5-dione
• CAS: 15180-22-0
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: CNXWPOWVDIUTPS-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  cyclo(Ala-Phe) 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 1-benzhydryl-2-benzyl-5-methylpiperazine
  参考文献：
  名称：

  催化不对称合成取代吗啉和哌嗪

  摘要：

  在以下两种情况下：3族取代吗啉的模块化和对映选择性合成以及2，5-取代哌嗪的非对映选择性合成中具有第4类金属催化的加氢胺化作用。

  DOI：

  10.1002/anie.201206826
• 作为产物：
  描述：

  在 磷酸二丁酯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以60%的产率得到cyclo(Ala-Phe)
  参考文献：
  名称：

  磷酸二丁酯（DBP）介导的氨基酯合成环状N，N′-二取代脲衍生物的比较研究

  摘要：

  的Ñ，Ñ '二取代的脲衍生物如氨基酸乙内酰脲和二氢尿嘧啶衍生物制备来自使用磷酸二丁酯（DBP）的天然和非天然氨基酸酯起始。在试图合成具有大于六元环的N-杂环的N-杂环的过程中，所述六元环包含N，N′-二取代的尿素官能团，分离了三种意想不到的产物，即扁豆酚酮，N-甲基吡咯烷-2-酮和二酮哌嗪。

  DOI：

  10.1016/j.tetlet.2012.08.083

文献信息

• Facile one-step synthesis of 2,5-diketopiperazines
  作者：Xianyu Sun、Rachita Rai、Alexander D. MacKerell、Alan I. Faden、Fengtian Xue

  DOI：10.1016/j.tetlet.2014.01.133

  日期：2014.3

  We report a one-step protocol for the general synthesis of 2,5-diketopiperazines from an Fmoc-protected amino acid and an amino acid ester. The application of the method is highlighted by rapid and efficient preparation of various 2,5-diketopiperazines.

  我们报告了从Fmoc保护的氨基酸和氨基酸酯一般合成2,5-二酮哌嗪的一步协议。快速有效地制备各种2，5-二酮哌嗪类药物突显了该方法的应用。
• Synthesis and Conformational Characterization of Diketopiperazines Bearing a Benzyl Moiety
  作者：Michiyasu Nakao、Yuriko Toriuchi、Shintaro Fukayama、Shigeki Sano

  DOI：10.1246/cl.131001

  日期：2014.3.5

  Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1H NMR spectroscopy. All of these diketopiperazines were found to adopt a folded conforma...

  合成带有苄基部分和不同对位取代基的二酮哌嗪并通过 1 H NMR 光谱分析。发现所有这些二酮哌嗪都采用折叠的构形...
• Isolation and Structural Determination of the Antifouling Diketopiperazines from Marine-Derived <i>Streptomyces praecox</i> 291-11
  作者：Ji Young CHO、Ji Young KANG、Yong Ki HONG、Hyo Hyun BAEK、Hyoun Woong SHIN、Myoung Sug KIM

  DOI：10.1271/bbb.110943

  日期：——

  Marine derived actinomycetes constituting 185 strains were screened for their antifouling activity against the marine seaweed, Ulva pertusa, and fouling diatom, Navicula annexa. Strain 291-11 isolated from the seaweed, Undaria pinnatifida, rhizosphere showed the highest antifouling activity and was identified as Streptomyces praecox based on a 16S rDNA sequence analysis. Strain 291-11 was therefore named S. praecox 291-11. The antifouling compounds from S. praecox 291-11 were isolated, and their structures were analyzed. The chemical constituents representing the antifouling activity were identified as (6S,3S)-6-benzyl-3-methyl-2,5-diketopiperazine (bmDKP) and (6S,3S)-6-isobutyl-3-methyl-2,5-diketopiperazine (imDKP) by interpreting the nuclear magnetic resonance and high-resolution mass spectroscopy data. Approximately 4.8 mg of bmDKP and 3.1 mg of imDKP were isolated from 1.2 g of the S. praecox 291-11 crude extract. Eight different compositions of culture media were investigated for culture, the TBFeC medium being best for bmDKP and TCGC being the optimum for imDKP production. Two compounds respectively showed a 17.7 and 21 therapeutic ratio (LC50/EC50) to inhibit zoospores, and two compounds respectively showed a 263 and 120.2 therapeutic ratio to inhibit diatoms.

  对 185 株海洋放线菌进行了筛选，以检测它们对海洋海藻百舌莼和污点硅藻 Navicula annexa 的防污活性。根据 16S rDNA 序列分析，从海藻 Undaria pinnatifida 根瘤中分离出的 291-11 株菌株显示出最高的防污活性，并被鉴定为 praecox 链霉菌。因此，菌株 291-11 被命名为 S. praecox 291-11。从 S. praecox 291-11 中分离出了防污化合物，并对其结构进行了分析。通过解释核磁共振和高分辨率质谱数据，确定了代表防污活性的化学成分为（6S,3S）-6-苄基-3-甲基-2,5-二酮哌嗪（bmDKP）和（6S,3S）-6-异丁基-3-甲基-2,5-二酮哌嗪（imDKP）。从 1.2 克 S. praecox 291-11 粗提取物中分离出约 4.8 毫克 bmDKP 和 3.1 毫克 imDKP。研究了八种不同成分的培养基，其中 TBFeC 培养基最适于生产 bmDKP，TCGC 培养基最适于生产 imDKP。两种化合物分别显示出 17.7 和 21 的治疗比（LC50/EC50）来抑制动物孢子，两种化合物分别显示出 263 和 120.2 的治疗比来抑制硅藻。
• Preparation of novel 2-(trialkylsilyl)ethyl linkers and first synthesis of Tryprostatin B on solid phase
  作者：Bingbing Wang、Li Chen、Kyungjin Kim

  DOI：10.1016/s0040-4039(00)02312-1

  日期：2001.2

  methods for novel polymer-supported 2-(trialkylsilyl)ethanol linkers 3 are described. The new silyl linker has been examined as a C-terminal linkage to provide several diketopiperazines. Using this synthetic method, the first solid phase synthesis of Tryprostatin B was accomplished. Several functionalized 2-(trialkylsilyl)ethyl linkers 12–17 are synthesized from 2-(trialkylsilyl)ethanol linkers. During

  描述了用于新型聚合物负载的2-（三烷基甲硅烷基）乙醇接头3的两种合成方法。新的甲硅烷基连接基已作为C端连接基进行了研究，以提供几种二酮哌嗪。使用这种合成方法，完成了Tryprostatin B的第一个固相合成。几个官能2-（三烷基甲硅烷）乙基接头12 - 17从2-（三烷基甲硅烷）乙醇接头合成。在制备过程中，新的甲硅烷基连接基证明对各种反应条件具有抵抗力，例如碱性和中度酸性介质，氧化和高温条件。
• Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides
  作者：Christopher Bérubé、Xavier Barbeau、Sébastien Cardinal、Pierre-Luc Boudreault、Corinne Bouchard、Nicolas Delcey、Patrick Lagüe、Normand Voyer

  DOI：10.1080/10610278.2016.1236197

  日期：2017.5.4

  We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.[GRAPHICS].