cyclo-(Leu-Thr) | 71018-05-8

• 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-(Leu-Thr)
• 英文别名: cyclo(L-Leu-L-Thr)；(3S,6S)-3-[(1R)-1-hydroxyethyl]-6-(2-methylpropyl)piperazine-2,5-dione
• CAS: 71018-05-8
• 化学式: C₁₀H₁₈N₂O₃
• 分子量: 214.265
• InChiKey: UBJFWFZZUVUIOS-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-Leucine, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-threonyl]-, methyl ester 在 N-甲基吗啉 、 盐酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 仲丁醇 为溶剂， 反应 3.5h， 生成 cyclo-(Leu-Thr)
  参考文献：
  名称：

  Cyclic dipeptides exhibit potency for scavenging radicals

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2012.01.050

文献信息

• Concise Synthesis of 2,5-Diketopiperazines via Catalytic Hydroxy-Directed Peptide Bond Formations
  作者：Masayoshi Koshizuka、Kaito Shinoda、Kazuishi Makino、Naoyuki Shimada

  DOI：10.1021/acs.joc.3c00195

  日期：2023.6.2

  concise synthesis of this type of DKPs through diboronic acid anhydride-catalyzed hydroxy-directed peptide bond formations. The sequential reactions in this report, which consist of three steps, an intermolecular catalytic condensation reaction in which water is the only byproduct, a simple deprotection of the nitrogen-protecting group, and an intramolecular cyclization, enabled the synthesis of functionalized

  具有羟甲基官能团的 2,5-二酮哌嗪 (DKP) 是许多生物活性分子和功能材料中的必需结构。我们已经建立了一个简单的协议，用于通过二硼酸酐催化的羟基定向肽键形成简明合成此类 DKP。本报告中的连续反应由三个步骤组成，其中水是唯一的副产物的分子间催化缩合反应、氮保护基团的简单脱保护和分子内环化，使功能化 DKPs 的合成成为可能。无需任何中间纯化即可获得优异的产量。该协议的效用已通过合成天然产物、phomamide 和 Cyclo(Deala- l -Leu) 得到证明。
• 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.