Z-L-Ile-L-Glu-OH | 55559-25-6

• 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: Z-L-Ile-L-Glu-OH
• 英文别名: N²-(N-benzyloxycarbonyl-L-isoleucyl)-L-glutamine
• CAS: 55559-25-6
• 化学式: C₁₉H₂₇N₃O₆
• 分子量: 393.44
• InChiKey: ONWKJJQNRRSCQY-NOLJZWGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  147.82
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z-L-Ile-L-Glu-OH 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.5h， 生成
  参考文献：
  名称：

  Optimization of Subsite Binding to the β5 Subunit of the Human 20S Proteasome Using Vinyl Sulfones and 2-Keto-1,3,4-oxadiazoles:  Syntheses and Cellular Properties of Potent, Selective Proteasome Inhibitors

  摘要：

  Beginning with the peptide sequence Cbz-Ile-Glu(OtBu)-Ala-Leu found in PSI (3), a series of vinyl sulfones (VS) were synthesized for evaluation as inhibitors of the chymotrypsin-like activity of the 20S proteasome. Variations at the key P3 position confirmed the importance of a long side chain capped with a hydrophobic group for optimal potency, consistent with a model of binding to the S3 subsite. The tert-butyl glutamic ester initially used at P3 gave plasma unstable, insoluble compounds and was replaced with the better isostere, N-beta-neopentyl asparagine. The inhibitors were shortened by replacing the N-terminal Cbz-isoleucine with a p-tosyl group without loss of potency. Small L-amino acids were used at P2, where D-substitution was not tolerated. The resulting optimized P4-P3-P2 sequence was grafted onto a novel proteasome inhibitor warhead, 2-keto-1,3,4-oxadiazoles (KOD), to produce reversible, subnanomolar proteasome inhibitors that were 1000-fold selective versus cathepsin B (CatB), cathepsin S (CatS), and trypsin-like as well as PGPH-like proteasome activity. A number of compounds in both the VS and the KOD series exhibited growth inhibitory effects against the human prostate cancer cell line PC3 at submicromolar concentrations.

  DOI：

  10.1021/jm058289o
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氨 、 sodium 作用下， 生成 Z-L-Ile-L-Glu-OH
  参考文献：
  名称：

  The Synthesis of p-Toluenesulfonyl-L-isoleucyl-L-glutaminyl- L-asparagine and Related Peptides¹

  摘要：

  DOI：

  10.1021/ja01641a003

文献信息

• Enzymatic synthesis of new antimicrobial peptides for food purposes
  作者：Mauricio Adaro、Ángel Gabriel Salinas Ibáñez、Anabella Lucia Origone、Diego Vallés、Fanny Guzmán、Alba Vega、Sonia Barberis

  DOI：10.3389/fmicb.2023.1153135

  日期：——

  synthetic antibiotics has prompted the search for more natural preservatives that can improve the safety and quality of food. In this study we report the enzymatic synthesis of N-α-[Carbobenzyloxy]-Ile-Gln (Z-IQ) which is the precursor of Ile-Gln (IQ), a new antibacterial dipeptide, using an aqueous–organic biphasic system formed by 50% (v/v) ethyl acetate in 0.1 M Tris – HCl buffer pH 8. A partially purified

  消费者越来越意识到合成抗生素对健康的潜在负面影响，这促使人们寻找更多可以提高食品安全性和质量的天然防腐剂。在这项研究中，我们报告了 N-α-[苄氧羰基]-Ile-Gln (Z-IQ) 的酶促合成，它是 Ile-Gln (IQ) 的前体，一种新的抗菌二肽，使用形成的水-有机双相系统50% (v/v) 乙酸乙酯，溶于 0.1 M Tris – HCl 缓冲液 pH 8。部分纯化的蛋白水解提取物来自麻风颗粒茄，名为 granulosain，被证明是用于合成 Z-IQ 的强大生物催化剂，在上述条件下可产生 71 ± 0.10% 的最大肽产量。切割和纯化 IQ 二肽后，对抗菌活性进行了测定金黄色葡萄球菌ATCC 25923,人型葡萄球菌A17771，和金黄色葡萄球菌C00195，MIC 值介于 118 ± 0.01 μg/mL 和 133.7 ± 0.05 μg/mL 之间。此外，IQ 显示 MIC
• Peptide synthesis with benzisoxazolium salts—III
  作者：D.S. Kemp、S.J. Wrobel、S-W. Wang、Z. Bernstein、J. Rebek

  DOI：10.1016/s0040-4020(01)97372-7

  日期：1974.1