2-((S)-1-tert-Butoxycarbonylamino-ethyl)-oxazole-4-carboxylic acid | 647011-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((S)-1-tert-Butoxycarbonylamino-ethyl)-oxazole-4-carboxylic acid
• 英文别名: 2-{(1S)-1-[(tert-Butoxycarbonyl)amino]ethyl}-1,3-oxazole-4-carboxylic acid；2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1,3-oxazole-4-carboxylic acid
• CAS: 647011-10-7
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: MOWRGFGIKJOEGX-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((S)-1-tert-Butoxycarbonylamino-ethyl)-oxazole-4-carboxylic acid 在 lithium hydroxide 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Structure–activity based study of the Smac-binding pocket within the BIR3 domain of XIAP

  摘要：

  A small series of peptide mimics was designed and synthesized to contain a heterocyclic ring in place of the potentially labile N-terminal peptide bond of the tetrapeptide containing the Smac-XIAP-binding motif. Two Smac mimics were shown to bind to the BIR3 domain of XIAP with moderate affinity and one displayed increased activity in cells relative to the Smac peptides. The structures of BIR3-XIAP in complex with a Smac peptide and a peptide mimic were solved and analyzed to elucidate the structure-activity relationship surrounding the Smac-binding domain within BIR3-XIAP. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.010
• 作为产物：
  描述：

  Boc-L-Ala-L-Ser-OMe 在 二乙胺基三氟化硫 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-((S)-1-tert-Butoxycarbonylamino-ethyl)-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and anticancer mechanistic studies of linked azoles

  摘要：

  在此，我们报告了2,4-偶联咪唑含有分子的合成和生物活性评估。

  DOI：

  10.1039/c4md00387j

文献信息

• Late-Stage Macrocyclization of Bioactive Peptides with Internal Oxazole Motifs via Palladium-Catalyzed C–H Olefination
  作者：Shu Liu、Chuangxu Cai、Zengbing Bai、Wangjian Sheng、Jiantao Tan、Huan Wang

  DOI：10.1021/acs.orglett.1c00580

  日期：2021.4.16

  the synthesis and direct functionalization of complex oxazole-containing peptides are in high demand. Herein, we report the late-stage site-selective functionalization of oxazole-containing peptides via palladium-catalyzed δ-C(sp2)–H olefination of phenylalanine, tryptophan, and tyrosine residues. This strategy utilizes oxazole motifs as internal directing groups and provides access to oxazole-containing

  恶唑是一种重要的药效团，存在于许多生物活性肽天然产物和肽模拟物的骨架中。对复杂的含恶唑肽的合成和直接功能化的有效方法有很高的需求。在此，我们报告了通过钯催化的苯丙氨酸、色氨酸和酪氨酸残基的δ-C(sp 2 )-H 烯化作用对含恶唑肽进行后期位点选择性功能化。该策略利用恶唑基序作为内部导向基团，并提供了获得具有生物活性的含恶唑肽大环化合物的途径。
• Synthesis and biological evaluation of analogues of the marine cyclic depsipeptide obyanamide
  作者：Wei Zhang、Ning Ding、Yingxia Li

  DOI：10.1002/psc.1361

  日期：2011.7

  to the results, the β‐amino acid residue was found to play a critical role in the biological activities. Additionally, the ester bond along with the Ala(Thz) moiety was also essential for biological activities. However, it seems too early to draw a conclusion that the N‐methylation of Val/Phe can lead to higher or lower cytotoxic activities. Copyright © 2011 European Peptide Society and John Wiley

  在奥巴酰胺的总合成的基础上，通过以下方法合成了该海洋环状双缩肽的20个类似物：（i）使用Z / OtBu方案在西半球中制备三肽片段；（ii）使用Boc / OMe方案在东半球制备二肽片段；（iii）在最后一步中偶联片段，除去保护基团（Boc和OtBu，在一个锅中），以及大环化。细胞毒性测试表明，三种合成化合物对HL-60，KB，LOVO和A549细胞系表现出中等活性。根据结果​​，发现β-氨基酸残基在生物活性中起关键作用。此外，酯键以及Ala（Thz）部分对于生物活性也是必不可少的。但是，现在得出结论认为Val / Phe的N-甲基化可导致更高或更低的细胞毒活性。版权所有©2011欧洲肽协会和John Wiley＆Sons，Ltd.。
• Oxazole-modified glycopeptides that target arthritis-associated class II MHC Aq and DR4 proteins
  作者：Ida E. Andersson、Tsvetelina Batsalova、Balik Dzhambazov、Lotta Edvinsson、Rikard Holmdahl、Jan Kihlberg、Anna Linusson

  DOI：10.1039/c003640d

  日期：——

  The glycopeptide CII259-273, a fragment from type II collagen (CII), can induce tolerance in mice susceptible to collagen-induced arthritis (CIA), which is a validated disease model for rheumatoid arthritis (RA). Here, we describe the design and synthesis of a small series of modified CII259-273 glycopeptides with oxazole heterocycles replacing three potentially labile peptide bonds. These glycopeptidomimetics were evaluated for binding to murine CIA-associated Aq and human RA-associated DR4 class II major histocompatibility complex (MHC) proteins. The oxazole modifications drastically reduced or completely abolished binding to Aq. Two of the glycopeptidomimetics were, however, well tolerated in binding to DR4 and they also induced strong responses by one or two DR4-restricted T-cell hybridomas. This work contributes to the development of an altered glycopeptide for inducing immunological tolerance in CIA, with the long-term goal of developing a therapeutic vaccine for treatment of RA.

  糖肽 CII259-273 是 II 型胶原蛋白（CII）的一个片段，它能诱导易患胶原诱导性关节炎（CIA）的小鼠产生耐受性，CIA 是类风湿性关节炎（RA）的一种有效疾病模型。在这里，我们描述了设计和合成一小系列改性 CII259-273 糖肽的过程，这些糖肽用噁唑杂环取代了三个潜在的易变肽键。我们评估了这些拟糖肽与小鼠 CIA 相关 Aq 和人类 RA 相关 DR4 II 类主要组织相容性复合体 (MHC) 蛋白的结合情况。草唑修饰可显著减少或完全消除与 Aq 的结合。不过，其中两种拟糖肽类药物与 DR4 的结合耐受性很好，它们还能诱导一两种 DR4 限制性 T 细胞杂交瘤产生强烈反应。这项工作有助于开发一种可诱导CIA免疫耐受的改变糖肽，其长远目标是开发一种治疗RA的疫苗。
• Synthesis and Antimicrobial Activity <i>in Vitro</i> of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties
  作者：Mincho Stanchev、Svoboda Tabakova、Georgi Videnov、Evgeny Golovinsky、Guenther Jung

  DOI：10.1002/(sici)1521-4184(19999)332:9<297::aid-ardp297>3.0.co;2-#

  日期：1999.9

  2-(Pyrrolidinyl)thiazole-4-carboxylic acid 5d, 2-(1-aminoalkyl)thiazole-4-carboxamides and hydrazides 8, 10 have been synthesized using alanine, valine, and proline as educts. In addition oxazole amino acids derived from leucine 20a and alanine 20b and some peptides 13, 14, 16 containing the 5-ring heterocyclic backbone modifications have been prepared. The thiazole and oxazole containing amino acids and peptides showed moderate antibacterial activity in vitro against various Gram-positive (Staphylococcus aureus, Bacillus cereus, etc.) and Gram-negative (Escherichia coli, Proteus vulgar is, etc.) bacteria, fungi (Candida albicans), and yeast (Saccharomyces cerevisae, etc.).