(3S,6S)-3-methyl-6-(2-methylpropyl)piperazine-2,5-dione | 1803-60-7

• 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: (3S,6S)-3-methyl-6-(2-methylpropyl)piperazine-2,5-dione
• 英文别名: (3S,6S)-6-isobutyl-3-methyl-2,5-diketopiperazine；(3S,6S)-3-isobutyl-6-methylpiperazine-2,5-dione；cyclo(Leu-Ala)；cyclo-(L-Leu-L-Ala)；cis-cyclo(Ala-Leu)；cis-cyclo(Leu-Ala)
• CAS: 1803-60-7；5845-58-9；5845-60-3；24676-83-3；35590-72-8；125410-18-6
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: DBJPZCJQDRPOME-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3-methyl-6-(2-methylpropyl)piperazine-2,5-dione 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 乙基4,7-二硫杂-1-氮杂二环[4.3.0]壬-5,8-二烯-5-羧酸酯
  参考文献：
  名称：

  15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5-dioxopiperazines)

  摘要：

  AbstractVarious cyclodipeptides containing glycine, alanine, leucine, valine, phenylalanine, phenylglycine and sarcosine units were synthesized by cyclization of dipeptide pentachlorophenyl esters. The 13C and natural abundance 15N NMR spectra of these heterocycles were measured in trifluoroacetic acid and compared with the spectra of the corresponding amino acids and polypeptides. The 13C NMR carbonyl signals of all cyclodipeptides show a 1.5–4.0 ppm upfield shift relative to the corresponding polypeptides. The 15N NMR signals show no such consistent relationship. The substituent effects and the neighbouring residue effects observed in the 15N NMR spectra of the cyclodipeptides are different from those of polypeptides, while the one bond NH coupling constant of cis and trans amide groups was almost identical. The nitrogen and the carbonyl signal of the Gly units in cyclo‐Gly‐Phe show an extraordinary downfield shift, reflecting the interaction of the phenyl group with the 2,5‐dioxopiperazine ring.

  DOI：

  10.1002/mrc.1270130111
• 作为产物：
  描述：

  L-亮氨酸-L-丙氨酸 生成 (3S,6S)-3-methyl-6-(2-methylpropyl)piperazine-2,5-dione
  参考文献：
  名称：

  Butenandt et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1951, vol. 288, p. 279,283

  摘要：

  DOI：

文献信息

• Onium salt supported peptide synthesis
  作者：Céline Roche、Mathieu Pucheault、Michel Vaultier、Alain Commerçon

  DOI：10.1016/j.tet.2010.07.016

  日期：2010.10

  Task specific ionic liquids and onium salts have been used as soluble supports for peptide synthesis. These new supports combine easy monitoring, high loading capacities, large scale preparation, and homogeneous kinetics characteristics while keeping advantages of solid-phase synthesis including easy purification and workup. Careful structural design of these supports allowed for fine tuning of physical

  任务特定的离子液体和鎓盐已用作肽合成的可溶性载体。这些新的支持物结合了易于监测，高负载能力，大规模制备和均相动力学特性的优点，同时保持了固相合成的优势，包括易于纯化和后处理。这些载体的精心结构设计允许对物理性质进行微调，从而获得更好的产率，动力学和纯度。
• 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。
• Cyclic dipeptides exhibit potency for scavenging radicals
  作者：Tadashi Furukawa、Takashi Akutagawa、Hitomi Funatani、Toshikazu Uchida、Yoshihiro Hotta、Masatake Niwa、Yoshiaki Takaya

  DOI：10.1016/j.bmc.2012.01.050

  日期：2012.3

  Twenty kinds of cyclic dipeptides containing L-leucine were synthesized, and their antioxidant activity against (OH)-O-center dot and O-2(center dot-) was investigated. Compounds possessing polar amino acid residues, such as Asp, Cys, Glu, Lys, Pro, Ser, and Trp, exhibited higher antioxidant activity against (OH)-O-center dot than vitamin E. However, only cyclo(L-Cys-L-Leu) scavenged O-2(center dot-). (C) 2012 Elsevier Ltd. All rights reserved.
• 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].
• Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
  作者：Gaëlle Simon、Christopher Bérubé、Normand Voyer、Daniel Grenier

  DOI：10.1016/j.bmc.2018.11.042

  日期：2019.6

  Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure-activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.