cyclo-(L-alanyl-trans-4-hydroxy-L-prolyl) | 67943-21-9

• 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-(L-alanyl-trans-4-hydroxy-L-prolyl)
• 英文别名: (3S,7R,8aS)-7-hydroxy-3-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione；cyclo-(L-Ala-trans-4-hydroxy-L-Pro)；cyclo(Ala-Hyp)；cyclo(L-Hyp-L-Ala)；(3S,7R,8aS)-7-hydroxy-3-methyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 67943-21-9
• 化学式: C₈H₁₂N₂O₃
• 分子量: 184.195
• InChiKey: JBVUOARNEYAAOS-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclo-(L-alanyl-trans-4-hydroxy-L-prolyl) 在 sodium tetrahydroborate 、 碘 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(3S,7R,8aS)-3-methyloctahydropyrrolo[1,2-a]pyrazine-7-ol
  参考文献：
  名称：

  Enantiomerically pure piperazines via NaBH4/I2 reduction of cyclic amides

  摘要：

  Enantiomerically pure (3S,7R,8aS)-3-phenyloctahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-methyl octahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-isopropyloctahydropyrrolo[1,2-a]pyrazine-7-ol and (35,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol 16d were synthesized via preparation of the corresponding cyclic amides from enantiomerically pure L-proline and hydroxyproline derivatives followed by reduction using sodium borohydride-iodine. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.002
• 作为产物：
  描述：

  (2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)aminopropanoyl-4'-hydroxypyrrolidine-2'-carboxylate 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 仲丁醇 为溶剂， 反应 19.0h， 以78%的产率得到cyclo-(L-alanyl-trans-4-hydroxy-L-prolyl)
  参考文献：
  名称：

  Enantiomerically pure piperazines via NaBH4/I2 reduction of cyclic amides

  摘要：

  Enantiomerically pure (3S,7R,8aS)-3-phenyloctahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-methyl octahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-isopropyloctahydropyrrolo[1,2-a]pyrazine-7-ol and (35,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol 16d were synthesized via preparation of the corresponding cyclic amides from enantiomerically pure L-proline and hydroxyproline derivatives followed by reduction using sodium borohydride-iodine. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.002

文献信息

• Solid-phase synthesis of diketopiperazines, useful scaffolds for combinatorial chemistry
  作者：Montserrat del Fresno、Jordi Alsina、Miriam Royo、George Barany、Fernando Albericio

  DOI：10.1016/s0040-4039(98)00226-3

  日期：1998.4

  dipeptides, are often formed by a side reaction of solid-phase peptide synthesis. Using the new “Backbone Amide Linker,” this chemistry can be conveniently harnessed for the intentional preparation of diketopiperazines. These products will be useful scaffolds for combinatorial chemistry, since they incorporate three different points of diversity: both amino acid side-chains and one (of the two) amide bonds

  环状二肽二酮哌嗪通常由固相肽合成的副反应形成。使用新的“骨架酰胺连接剂”，可以方便地利用这种化学方法有意地制备二酮哌嗪。这些产品对于组合化学将是有用的支架，因为它们结合了三个不同的多样性点：两个氨基酸侧链和一个（两个）酰胺键。
• Identification of Collagen-Derived Hydroxyproline (Hyp)-Containing Cyclic Dipeptides with High Oral Bioavailability: Efficient Formation of Cyclo(X-Hyp) from X-Hyp-Gly-Type Tripeptides by Heating
  作者：Yuki Taga、Masashi Kusubata、Kiyoko Ogawa-Goto、Shunji Hattori

  DOI：10.1021/acs.jafc.7b03714

  日期：2017.11.1

  reported to demonstrate antioxidant, antidepressant, and other beneficial effects. We recently developed a novel collagen hydrolysate characterized by a high content of X-hydroxyproline (Hyp)-Gly-type tripeptides using ginger protease. In the present study, we found that, through heating, X-Hyp-Gly can be easily converted into Hyp-containing cyclic dipeptides. After heating for 3 h at 85 °C and pH 4.8, Ala-Hyp-Gly

  环状二肽（2,5-二酮哌嗪）存在于多种食品中，据报道具有抗氧化，抗抑郁和其他有益作用。我们最近开发了一种新型的胶原蛋白水解产物，其特征是使用生姜蛋白酶的X-羟脯氨酸（Hyp）-Gly型三肽含量高。在本研究中，我们发现通过加热，X-Hyp-Gly可以轻松转化为含Hyp的环状二肽。在85°C和pH 4.8下加热3小时后，Ala-Hyp-Gly几乎完全环化为环（Ala-Hyp），而Ala-Hyp则略微环化。在加热条件下，生姜降解的胶原蛋白水解物中环（Ala-Hyp）和环（Leu-Hyp）的含量分别达到0.5-1％（w / w）。使用小鼠的口服给药实验显示，与胶原蛋白寡肽（包括Pro-Hyp）相比，cyclo（Ala-Hyp）和cyclo（Leu-Hyp）被吸收到血液中的效率明显更高。胶原蛋白特异性环状二肽的高生产率和口服生物利用度表明，经热处理的生姜降解的胶原蛋白水解物具有显着的健康益处。
• ANTIFUNGAL COMPOSITIONS CONTAINING THE ENDOPHYTE FUNGUS ALTERNARIA ALTERNATA AND OR ITS METABOLITES, AS ANTAGONIST AGENTS OF PLASMOPARA VITICOLA
  申请人：Musetti Rita

  公开号：US20090257984A1

  公开（公告）日：2009-10-15

  The present invention relates to compositions containing the fungus Alternaria alternata and/or the secondary metabolites thereof, which belong to the family of the diketopiperazines (DKPs), for controlling the pathogen fungus Plasmopara viticola.
• Enantiomerically pure piperazines via NaBH4/I2 reduction of cyclic amides
  作者：Vagala Harish、Mariappan Periasamy

  DOI：10.1016/j.tetasy.2016.12.002

  日期：2017.1

  Enantiomerically pure (3S,7R,8aS)-3-phenyloctahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-methyl octahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-isopropyloctahydropyrrolo[1,2-a]pyrazine-7-ol and (35,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol 16d were synthesized via preparation of the corresponding cyclic amides from enantiomerically pure L-proline and hydroxyproline derivatives followed by reduction using sodium borohydride-iodine. (C) 2016 Elsevier Ltd. All rights reserved.

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