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1
A 13C-n.m.r. investigation of ionizations within a trypsin-inhibitor complex. Evidence that the pKa of histidine-57 is raised by interaction with the hemiketal oxyanion.对胰蛋白酶抑制剂复合物内电离作用的¹³C核磁共振研究。组氨酸-57的pKa因与半缩酮氧阴离子相互作用而升高的证据。
Biochem J. 1985 Nov 1;231(3):677-82. doi: 10.1042/bj2310677.
2
A 13C-n.m.r. investigation of the ionizations within an inhibitor--alpha-chymotrypsin complex. Evidence that both alpha-chymotrypsin and trypsin stabilize a hemiketal oxyanion by similar mechanisms.抑制剂-α-糜蛋白酶复合物内电离作用的13C核磁共振研究。α-糜蛋白酶和胰蛋白酶通过相似机制稳定半缩酮氧阴离子的证据。
Biochem J. 1989 Mar 15;258(3):853-9. doi: 10.1042/bj2580853.
3
A study of the stabilization of tetrahedral adducts by trypsin and delta-chymotrypsin.一项关于胰蛋白酶和δ-胰凝乳蛋白酶对四面体加合物稳定性影响的研究。
Biochem J. 1992 Sep 15;286 ( Pt 3)(Pt 3):889-900. doi: 10.1042/bj2860889.
4
13C NMR study of the ionizations within a trypsin-chloromethyl ketone inhibitor complex.胰蛋白酶-氯甲基酮抑制剂复合物内电离作用的13C核磁共振研究。
Biochemistry. 1985 Jul 2;24(14):3478-87. doi: 10.1021/bi00335a014.
5
Determination of the ionization state of the active-site histidine in a subtilisin-(chloromethane inhibitor) derivative by 13C-NMR.通过碳-13核磁共振法测定枯草杆菌蛋白酶-（氯甲烷抑制剂）衍生物中活性位点组氨酸的电离状态。
Biochem J. 1996 Jul 1;317 ( Pt 1)(Pt 1):35-40. doi: 10.1042/bj3170035.
6
15N and 1H NMR spectroscopy of the catalytic histidine in chloromethyl ketone-inhibited complexes of serine proteases.丝氨酸蛋白酶氯甲基酮抑制复合物中催化组氨酸的15N和1H核磁共振光谱
Biochemistry. 1996 Feb 20;35(7):2437-44. doi: 10.1021/bi9513968.
7
A 13C-NMR study of the role of Asn-155 in stabilizing the oxyanion of a subtilisin tetrahedral adduct.一项关于天冬酰胺-155在稳定枯草杆菌蛋白酶四面体加合物氧负离子中作用的13C核磁共振研究。
Biochem J. 1997 Sep 15;326 ( Pt 3)(Pt 3):861-6. doi: 10.1042/bj3260861.
8
13C and 1H NMR studies of ionizations and hydrogen bonding in chymotrypsin-glyoxal inhibitor complexes.胰凝乳蛋白酶-乙二醛抑制剂复合物中电离作用和氢键的13C与1H核磁共振研究
J Biol Chem. 2007 Mar 16;282(11):7852-61. doi: 10.1074/jbc.M611394200. Epub 2007 Jan 9.
9
Diastereotopic covalent binding of the natural inhibitor leupeptin to trypsin: detection of two interconverting hemiacetals by solution and solid-state NMR spectroscopy.天然抑制剂亮抑酶肽与胰蛋白酶的非对映异构共价结合：通过溶液和固态核磁共振光谱检测两种相互转化的半缩醛。
Biochemistry. 1991 Oct 15;30(41):10026-34. doi: 10.1021/bi00105a030.
10
pH-dependence of 13C chemical shifts and 13C,H coupling constants in imidazole and L-histidine.咪唑和L-组氨酸中13C化学位移及13C、H耦合常数的pH依赖性
Biochem J. 1975 Jun;147(3):605-7. doi: 10.1042/bj1470605.

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1
Kinetic Studies of the Effect of pH on the Trypsin-Catalyzed Hydrolysis of -α-benzyloxycarbonyl-l-lysine--nitroanilide: Mechanism of Trypsin Catalysis.pH对胰蛋白酶催化水解α-苄氧羰基-L-赖氨酸-对硝基苯胺影响的动力学研究：胰蛋白酶催化机制
ACS Omega. 2020 Mar 3;5(10):4915-4923. doi: 10.1021/acsomega.9b03750. eCollection 2020 Mar 17.
2
A new lysine derived glyoxal inhibitor of trypsin, its properties and utilization for studying the stabilization of tetrahedral adducts by trypsin.一种新型的源自赖氨酸的胰蛋白酶乙二醛抑制剂、其性质以及用于研究胰蛋白酶对四面体加合物的稳定作用
Biochem Biophys Rep. 2016 Jan 4;5:272-284. doi: 10.1016/j.bbrep.2015.12.015. eCollection 2016 Mar.
3
13C-NMR study of the inhibition of delta-chymotrypsin by a tripeptide-glyoxal inhibitor.三肽-乙二醛抑制剂对δ-胰凝乳蛋白酶抑制作用的13C核磁共振研究
Biochem J. 2002 Mar 1;362(Pt 2):339-47. doi: 10.1042/0264-6021:3620339.
4
A 13C-NMR study of the role of Asn-155 in stabilizing the oxyanion of a subtilisin tetrahedral adduct.一项关于天冬酰胺-155在稳定枯草杆菌蛋白酶四面体加合物氧负离子中作用的13C核磁共振研究。
Biochem J. 1997 Sep 15;326 ( Pt 3)(Pt 3):861-6. doi: 10.1042/bj3260861.
5
Determination of the ionization state of the active-site histidine in a subtilisin-(chloromethane inhibitor) derivative by 13C-NMR.通过碳-13核磁共振法测定枯草杆菌蛋白酶-（氯甲烷抑制剂）衍生物中活性位点组氨酸的电离状态。
Biochem J. 1996 Jul 1;317 ( Pt 1)(Pt 1):35-40. doi: 10.1042/bj3170035.
6
A study of the stabilization of the oxyanion of tetrahedral adducts by trypsin, chymotrypsin and subtilisin.一项关于胰蛋白酶、胰凝乳蛋白酶和枯草杆菌蛋白酶对四面体加合物氧阴离子稳定性的研究。
Biochem J. 1995 Apr 15;307 ( Pt 2)(Pt 2):353-9. doi: 10.1042/bj3070353.
7
A 13C-n.m.r. investigation of the ionizations within an inhibitor--alpha-chymotrypsin complex. Evidence that both alpha-chymotrypsin and trypsin stabilize a hemiketal oxyanion by similar mechanisms.抑制剂-α-糜蛋白酶复合物内电离作用的13C核磁共振研究。α-糜蛋白酶和胰蛋白酶通过相似机制稳定半缩酮氧阴离子的证据。
Biochem J. 1989 Mar 15;258(3):853-9. doi: 10.1042/bj2580853.
8
Inactivation of the RTEM-1 cysteine beta-lactamase by iodoacetate. The nature of active-site functional groups and comparisons with the native enzyme.碘乙酸对RTEM-1半胱氨酸β-内酰胺酶的失活作用。活性位点官能团的性质及与天然酶的比较。
Biochem J. 1991 Jan 1;273(Pt 1)(Pt 1):85-91. doi: 10.1042/bj2730085.
9
A study of the relaxation parameters of a 13C-enriched methylene carbon and a 13C-enriched perdeuteromethylene carbon attached to chymotrypsin.一项关于与胰凝乳蛋白酶相连的富含13C的亚甲基碳和富含13C的全氘代亚甲基碳的弛豫参数的研究。
Biochem J. 1991 Dec 15;280 ( Pt 3)(Pt 3):649-57. doi: 10.1042/bj2800649.
10
A study of the stabilization of tetrahedral adducts by trypsin and delta-chymotrypsin.一项关于胰蛋白酶和δ-胰凝乳蛋白酶对四面体加合物稳定性影响的研究。
Biochem J. 1992 Sep 15;286 ( Pt 3)(Pt 3):889-900. doi: 10.1042/bj2860889.

本文引用的文献

1
Direct determination of the protonation states of aspartic acid-102 and histidine-57 in the tetrahedral intermediate of the serine proteases: neutron structure of trypsin.丝氨酸蛋白酶四面体中间体中天冬氨酸-102和组氨酸-57质子化状态的直接测定：胰蛋白酶的中子结构
Biochemistry. 1981 Oct 27;20(22):6462-74. doi: 10.1021/bi00525a027.
2
Transition-state stabilization at the oxyanion binding sites of serine and thiol proteinases: hydrolyses of thiono and oxygen esters.丝氨酸和硫醇蛋白酶氧负离子结合位点的过渡态稳定作用：硫代酯和氧酯的水解反应
Biochemistry. 1983 Jan 4;22(1):117-22. doi: 10.1021/bi00270a017.
3
Identification of the histidine residue at the active center of trypsin labelled by TLCK.鉴定经甲苯磺酰-L-赖氨酸氯甲基酮（TLCK）标记的胰蛋白酶活性中心的组氨酸残基。
Biochem Biophys Res Commun. 1967 May 5;27(3):391-7. doi: 10.1016/s0006-291x(67)80112-8.
4
High resolution nuclear magnetic resonance studies of the active site of chymotrypsin. I. The hydrogen bonded protons of the "charge relay" system.胰凝乳蛋白酶活性位点的高分辨率核磁共振研究。I. “电荷中继”系统的氢键质子。
J Mol Biol. 1974 Jul 5;86(3):519-40. doi: 10.1016/0022-2836(74)90178-8.
5
Affinity labelling of proteinases with tryptic specificity by peptides with C-terminal lysine chloromethyl ketone.用具有C端赖氨酸氯甲基酮的肽对具有胰蛋白酶特异性的蛋白酶进行亲和标记。
Biochem J. 1974 Mar;137(3):579-85. doi: 10.1042/bj1370579.
6
13C NMR study of the ionizations within a trypsin-chloromethyl ketone inhibitor complex.胰蛋白酶-氯甲基酮抑制剂复合物内电离作用的13C核磁共振研究。
Biochemistry. 1985 Jul 2;24(14):3478-87. doi: 10.1021/bi00335a014.
7
Polypeptide halomethyl ketones bind to serine proteases as analogs of the tetrahedral intermediate. X-ray crystallographic comparison of lysine- and phenylalanine-polypeptide chloromethyl ketone-inhibited subtilisin.多肽卤甲基酮作为四面体中间体类似物与丝氨酸蛋白酶结合。赖氨酸和苯丙氨酸多肽氯甲基酮抑制枯草杆菌蛋白酶的X射线晶体学比较。
J Biol Chem. 1976 Feb 25;251(4):1097-103.
8
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.
9
Carbon-13 nuclear magnetic resonance as a probe of side chain orientation and mobility in carboxymethylated human carbonic anhydrase B.碳-13核磁共振作为羧甲基化人碳酸酐酶B侧链取向和流动性的探针。
Biochemistry. 1978 Sep 5;17(18):3730-6. doi: 10.1021/bi00611a009.

对胰蛋白酶抑制剂复合物内电离作用的¹³C核磁共振研究。组氨酸-57的pKa因与半缩酮氧阴离子相互作用而升高的证据。

A 13C-n.m.r. investigation of ionizations within a trypsin-inhibitor complex. Evidence that the pKa of histidine-57 is raised by interaction with the hemiketal oxyanion.

作者信息

Primrose W U, Scott A I, Mackenzie N E, Malthouse J P

出版信息

Biochem J. 1985 Nov 1;231(3):677-82. doi: 10.1042/bj2310677.

DOI:10.1042/bj2310677
PMID:4074329
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1152802/
Abstract

The 13C-n.m.r. titration shifts of the alpha-methylene group of N-alkylated imidazoles are shown to be a sensitive probe of the ionization of the imidazolium ion. The 13C-n.m.r. titration shifts of both the intact and denatured/autolysed 2-13C- and 1-13C-enriched trypsin-7-amino-3-benzyloxycarbonylamino-1-chloroheptan-2-one (Z-Lys-CH2Cl) complexes are compared. The titration shift for the denatured/autolysed complex confirms that this ionization is due to deprotonation of the N-alkylated imidazolium ring of histidine-57. In the intact trypsin-inhibitor complex the titration shift due to the 1-13C-enriched carbon is anomalous. We conclude that this titration shift cannot arise solely from the ionization of the imidazolium ion of histidine-57 and that the pKa of the imidazolium ion of histidine-57 is raised in the trypsin-inhibitor complex. The relevance of these studies to the mechanism of action of the serine proteinases is discussed.

摘要

N-烷基化咪唑α-亚甲基基团的13C-核磁共振滴定位移被证明是咪唑鎓离子电离的灵敏探针。比较了完整的和变性/自溶的富含2-13C和1-13C的胰蛋白酶-7-氨基-3-苄氧羰基氨基-1-氯庚烷-2-酮（Z-赖氨酸-CH2Cl）复合物的13C-核磁共振滴定位移。变性/自溶复合物的滴定位移证实这种电离是由于组氨酸-57的N-烷基化咪唑环去质子化所致。在完整的胰蛋白酶-抑制剂复合物中，富含1-13C的碳引起的滴定位移是异常的。我们得出结论，这种滴定位移不能仅由组氨酸-57的咪唑鎓离子电离产生，并且在胰蛋白酶-抑制剂复合物中组氨酸-57的咪唑鎓离子的pKa升高。讨论了这些研究与丝氨酸蛋白酶作用机制的相关性。