环(L-苯丙氨酰-L-丝氨酰) | 35591-00-5

• 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
• 中文名称: 环(L-苯丙氨酰-L-丝氨酰)
• 英文名称: CYCLO(-PHE-SER)
• 英文别名: cis-cyclo(Phe-Ser)；cyclo(L-Ser-L-Phe)；cyclo(Ser-Phe)；(3S,6S)-3-benzyl-6-(hydroxymethyl)piperazine-2,5-dione
• CAS: 35591-00-5
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: WIJKWEYCUNYTGY-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  环(L-苯丙氨酰-L-丝氨酰) 在 glutathione S-transferase GliC 作用下， 生成
  参考文献：
  名称：

  一种专用的谷胱甘肽S-转移酶介导胶质毒素生物合成中碳-硫键的形成

  摘要：

  胶质毒素是人类病原体烟曲霉的毒力因子，烟曲霉是侵袭性曲霉病的主要原因。它的毒性是由桥二硫二酮哌嗪 (ETP) 支架的不寻常的跨环二硫键介导的。在这里，我们公开了专门的谷胱甘肽 S-转移酶 (GST) GliG 在酶促硫化中的关键作用。此外，我们表明加氧酶 GliC 对二酮哌嗪的双羟基化是谷胱甘肽加合物形成的先决条件。这是 GST 参与微生物次级代谢中酶促 CS 键形成的第一份报告。

  DOI：

  10.1021/ja201311d
• 作为产物：
  描述：

  N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanyl-L-serine benzyl ester 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以78%的产率得到环(L-苯丙氨酰-L-丝氨酰)
  参考文献：
  名称：

  Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

  摘要：

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.069

文献信息

• Phenylalanine-containing cyclic dipeptides – the lowest molecular weight hydrogelators based on unmodified proteinogenic amino acids
  作者：Alexander J. Kleinsmann、Boris J. Nachtsheim

  DOI：10.1039/c3cc44110e

  日期：——

  Cyclic dipeptides (diketopiperazines - DKPs) that are based on the proteinogenic amino acid phenylalanine in combination with serine, cysteine, glutamate, histidine and lysine are described as simple and remarkable low molecular weight hydrogelators. Blends of selected DKPs show remarkable pH-dependent properties and can be applied as easy to tune materials in drug delivery.

  基于蛋白氨基酸苯丙氨酸与丝氨酸，半胱氨酸，谷氨酸，组氨酸和赖氨酸结合的环状二肽（二酮哌嗪-DKPs）被描述为简单而引人注目的低分子量水凝胶化剂。所选DKP的共混物显示出显着的pH依赖特性，可作为易于调整的材料应用于药物输送。
• 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。
• [EN] FUMARATE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USE<br/>[FR] COMPOSÉS FUMARATE, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：NGUYEN MARK QUANG

  公开号：WO2016127186A1

  公开（公告）日：2016-08-11

  Fumarate compounds, pharmaceutical compositions comprising the fumarate compounds, and methods of using fumarate compounds and pharmaceutical compositions for treating neurodegenerative, inflammatory, and autoimmune disorders including multiple sclerosis, psoriasis, irritable bowel disorder, ulcerative colitis, arthritis, chronic obstructive pulmonary disease, asthma, Parkinson's disease, Huntington's disease, and amyotrophic lateral sclerosis are disclosed.
• Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs
  作者：Vanessa L. Campo、Maristela B. Martins、Carlos H.T.P. da Silva、Ivone Carvalho

  DOI：10.1016/j.tet.2009.04.069

  日期：2009.7

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.
• A Dedicated Glutathione <i>S</i>-Transferase Mediates Carbon–Sulfur Bond Formation in Gliotoxin Biosynthesis
  作者：Daniel H. Scharf、Nicole Remme、Andreas Habel、Pranatchareeya Chankhamjon、Kirstin Scherlach、Thorsten Heinekamp、Peter Hortschansky、Axel A. Brakhage、Christian Hertweck

  DOI：10.1021/ja201311d

  日期：2011.8.17

  Gliotoxin is a virulence factor of the human pathogen Aspergillus fumigatus , the leading cause of invasive aspergillosis. Its toxicity is mediated by the unusual transannular disulfide bridge of the epidithiodiketopiperazine (ETP) scaffold. Here we disclose the critical role of a specialized glutathione S-transferase (GST), GliG, in enzymatic sulfurization. Furthermore, we show that bishydroxylation

  胶质毒素是人类病原体烟曲霉的毒力因子，烟曲霉是侵袭性曲霉病的主要原因。它的毒性是由桥二硫二酮哌嗪 (ETP) 支架的不寻常的跨环二硫键介导的。在这里，我们公开了专门的谷胱甘肽 S-转移酶 (GST) GliG 在酶促硫化中的关键作用。此外，我们表明加氧酶 GliC 对二酮哌嗪的双羟基化是谷胱甘肽加合物形成的先决条件。这是 GST 参与微生物次级代谢中酶促 CS 键形成的第一份报告。