• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

苯甲酸盐在endo-5-[4'（5'）咪唑基]-双环[2.2.1]庚-endo-2-基反式肉桂酸酯水解中的催化作用：对丝氨酸蛋白酶催化的电荷转移机制的影响。

Benzoate catalysis in the hydrolysis of endo-5-[4'(5')imidazolyl]-bicyclo[2.2.1]hept-endo- 2-yl trans-cinnamate: Implications for the charge-transfer mechanism of catalysis by serine proteases.

机构信息

Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California 91125.

出版信息

Proc Natl Acad Sci U S A. 1980 Jun;77(6):3095-7. doi: 10.1073/pnas.77.6.3095.

DOI:10.1073/pnas.77.6.3095
PMID:16592829
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC349558/
Abstract

The acceleration, by a factor of 2500, of the hydrolysis of endo-5-[4'(5')imidazolyl]bicyclo[2.2.1]hept-endo- 2-yl trans-cinnamate by 0.5 M sodium benzoate in 42 mol% dioxane in water can be explained without resort to operation of a "charge-relay" mechanism similar to that often postulated to account for the enzymatic activity of serine proteases. The degree of ionization of 4-methylimidazole and of sodium benzoate in 42 mol% dioxane in water at 60 degrees C have been measured by NMR spectroscopy.

摘要

在 60°C 时，通过 NMR 光谱法测量了 42mol%二氧六环中的水、4-甲基咪唑和苯甲酸钠的离解度。0.5M 苯甲酸钠在 42mol%二氧六环中的水，可以将 5-[4'（5'）咪唑基]双环[2.2.1]庚-2-endo-2-基反肉桂酸酯的水解加速 2500 倍，这一过程无需采用类似于通常用来解释丝氨酸蛋白酶酶活性的“电荷传递”机制。

相似文献

1
Benzoate catalysis in the hydrolysis of endo-5-[4'(5')imidazolyl]-bicyclo[2.2.1]hept-endo- 2-yl trans-cinnamate: Implications for the charge-transfer mechanism of catalysis by serine proteases.苯甲酸盐在endo-5-[4'（5'）咪唑基]-双环[2.2.1]庚-endo-2-基反式肉桂酸酯水解中的催化作用：对丝氨酸蛋白酶催化的电荷转移机制的影响。
Proc Natl Acad Sci U S A. 1980 Jun;77(6):3095-7. doi: 10.1073/pnas.77.6.3095.
2
Model for "charge-relay": acceleration by carboxylate anion in intramolecular general base-catalyzed ester hydrolysis by the imidazolyl group.“电荷中继”模型：咪唑基在分子内广义碱催化的酯水解中被羧酸根阴离子加速。
Proc Natl Acad Sci U S A. 1977 Jul;74(7):2634-8. doi: 10.1073/pnas.74.7.2634.
3
Intramolecular general base-catalyzed ester hydrolyses by the imidazolyl group.由咪唑基进行的分子内广义碱催化的酯水解反应。
Proc Natl Acad Sci U S A. 1977 Jan;74(1):23-5. doi: 10.1073/pnas.74.1.23.
4
Au(I)-catalyzed cycloisomerization reaction of amide- or ester-tethered 1,6-enynes to bicyclo[3.2.0]hept-6-en-2-ones.金（I）催化酰胺或酯连接的1,6-烯炔环异构化为双环[3.2.0]庚-6-烯-2-酮的反应。
J Org Chem. 2009 Oct 16;74(20):7922-34. doi: 10.1021/jo901771p.
5
Do cleavages of amides by serine proteases occur through a stepwise pathway involving tetrahedral intermediates?丝氨酸蛋白酶对酰胺的裂解是通过涉及四面体中间体的逐步途径发生的吗？
Proc Natl Acad Sci U S A. 1979 Feb;76(2):557-60. doi: 10.1073/pnas.76.2.557.
6
Thermal isomerization of tricyclo[4.1.0.0(2,7)]heptane and bicyclo[3.2.0]hept-6-ene through the (E,Z)-1,3-cycloheptadiene intermediate.三环[4.1.0.0(2,7)]庚烷和双环[3.2.0]庚-6-烯通过(E,Z)-1,3-环庚二烯中间体的热异构化反应。
J Org Chem. 2003 Nov 14;68(23):9081-7. doi: 10.1021/jo035168s.
7
Investigation of a general base mechanism for ester hydrolysis in C-C hydrolase enzymes of the alpha/beta-hydrolase superfamily: a novel mechanism for the serine catalytic triad.α/β-水解酶超家族C-C水解酶中酯水解通用碱机制的研究：丝氨酸催化三联体的新机制
Org Biomol Chem. 2007 Feb 7;5(3):507-13. doi: 10.1039/b615605c. Epub 2006 Dec 19.
8
Experimental and theoretical studies on stereo- and regioselectivity in intramolecular nitrone-alkene cycloaddition of hept-6-enoses derived from carbohydrates.关于碳水化合物衍生的庚-6-烯糖分子内硝酮-烯烃环加成反应中立体选择性和区域选择性的实验与理论研究
J Org Chem. 2006 Apr 14;71(8):3253-63. doi: 10.1021/jo060348y.
9
trans-acetonide controlled endo-selective intramolecular nitrone-alkene cycloaddition of hept-6-enoses: a facile entry to calystegines, tropanes, and hydroxylated aminocycloheptanes.
Org Lett. 2007 Jan 18;9(2):207-9. doi: 10.1021/ol062621o.
10
Preparation of bicyclo[3.2.0]heptane-2-endo,7-endo-diols: 1,3-diols with a chiral rigid backbone.双环[3.2.0]庚烷-2-内型,7-内型二醇的制备：具有手性刚性骨架的1,3-二醇。
J Org Chem. 2004 Feb 20;69(4):1353-6. doi: 10.1021/jo035324v.

本文引用的文献

1
Role of a buried acid group in the mechanism of action of chymotrypsin.一个埋藏的酸性基团在胰凝乳蛋白酶作用机制中的作用。
Nature. 1969 Jan 25;221(5178):337-40. doi: 10.1038/221337a0.
2
Carbon nuclear magnetic resonance studies of the histidine residue in alpha-lytic protease. Implications for the catalytic mechanism of serine proteases.α-裂解蛋白酶中组氨酸残基的碳核磁共振研究。对丝氨酸蛋白酶催化机制的启示。
Biochemistry. 1973 Nov 6;12(23):4732-43. doi: 10.1021/bi00747a028.
3
Applications of natural-abundance nitrogen-15 nuclear magnetic resonance to large biochemically important molecules.天然丰度氮-15核磁共振在大型生物化学重要分子中的应用。
Proc Natl Acad Sci U S A. 1975 Dec;72(12):4696-700. doi: 10.1073/pnas.72.12.4696.
4
Mechanism of action of serine proteases: tetrahedral intermediate and concerted proton transfer.丝氨酸蛋白酶的作用机制：四面体中间体与协同质子转移
Biochemistry. 1976 Dec 14;15(25):5581-8. doi: 10.1021/bi00670a024.
5
Energetics of enzyme catalysis.酶催化的能量学
Proc Natl Acad Sci U S A. 1978 Nov;75(11):5250-4. doi: 10.1073/pnas.75.11.5250.
6
Model for "charge-relay": acceleration by carboxylate anion in intramolecular general base-catalyzed ester hydrolysis by the imidazolyl group.“电荷中继”模型：咪唑基在分子内广义碱催化的酯水解中被羧酸根阴离子加速。
Proc Natl Acad Sci U S A. 1977 Jul;74(7):2634-8. doi: 10.1073/pnas.74.7.2634.
7
Intramolecular general base-catalyzed ester hydrolyses by the imidazolyl group.由咪唑基进行的分子内广义碱催化的酯水解反应。
Proc Natl Acad Sci U S A. 1977 Jan;74(1):23-5. doi: 10.1073/pnas.74.1.23.