TPDYs:用于生物结合过程的应变宏循环二烯酸
Bernard D'Onofrio1, Corentin Cruché1, Kirsten N Hurdal2
1Department of Chemistry and Centre for Green Chemistry and Catalysis, Université de Montréal, 1375 Avenue Thérèse-Lavoie-Roux, Montréal, QC, H2V 0B3, Canada. shawn.collins@umontreal.ca.
概括
一种新的特二烯 (TPDY) 宏循环使有效的生物结合和SPAAC反应成为可能. 这种独特的分子为化学生物学和药物开发提供了新的可能性.
科学领域:
- 有机化学 有机化学
- 化学生物学 化学生物学
- 宏分子化学 宏分子化学
背景情况:
- 应变促进的亚酸循环添加 (SPAAC) 是生物结合的关键点击化学反应.
- 目前正在开发具有独特反应性和稳定性的新型cyclooctyne替代品.
- 与线性或小环系统相比,宏循环支架具有独特的结构和电子特性.
研究的目的:
- 为了合成和表征一种新的特二烯 (TPDY) 宏循环.
- 评估TPDY宏循环在SPAAC和其他循环加法反应中的反应性.
- 为了证明TPDY对蛋白质生物结合的有用性.
主要方法:
- 3,5-二烯 (TPDY) 大循环的合成.
- 调查SPAAC与化物产生亚特罗皮索米三醇的反应.
- 探讨使用二乙酸盐和四酸盐的循环添加物.
- 使用微生物转胺酶对TPDY与蛋白质的生物结合.
主要成果:
- 成功合成含有TPDY宏循环的曲的1,3-diyne.
- TPDY在SPAAC中表现出活性,形成了三醇产物.
- TPDY经过了与二乙酸盐和四酸盐的循环添加.
- 通过微生物转谷氨酸酶催化反应,实现了TPDY与两个蛋白质的有效生物结合.
- TPDY二烯的稳定通过π和π*轨道相互作用发生,与典型的SPAAC试剂不同.
结论:
- 开发的TPDY宏循环是点击化学的多功能构建块.
- TPDY促进了基体三醇的形成和蛋白质生物结合.
- 在TPDY中对diyne的独特电子稳定扩大了SPAAC试剂的范围.
相关概念视频
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.1K
Cycloaddition Reactions: Overview
2.5K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.5K
Structure of Conjugated Dienes
4.9K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
4.9K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
3.8K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.8K
Stability of Conjugated Dienes
3.3K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
3.3K


