1may

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spinqualitylabelsall models 1may, resolution 1.8Å Show:Asymmetric Unit Biological Assembly Drag the structure with the mouse to rotate   Export Animated Image

BETA-TRYPSIN PHOSPHONATE INHIBITED

Overview

X-ray structures of trypsin from bovine pancreas inactivated by diphenyl, [N-(benzyloxycarbonyl)amino](4-amidinophenyl)methanephosphonate, [Z-(4-AmPhGly)P(OPh)2] were determined at 113 and 293 K to 1.8 angstrom, resolution and refined to R factors of 0.211 (113 K) and 0. 178 (293 K)., The structures reveal a tetrahedral phosphorus covalently bonded to the O, gamma of the active site serine. Covalent bond formation is accompanied by, the loss of both phenoxy groups. The D-stereoisomer of, Z-(4-AmPhGly)P-(OPh)2 is not observed in the complex. The L-stereoisomer, of the inhibitor forms contacts with several residues in the trypsin, active site. One of the phosphonate oxygens is inserted into the oxyanion, hole and forms hydrogen bonds to the amides of Gly193, Asp194, and Ser195., The second phosphonate oxygen forms hydrogen bonds to N epsilon 2 of His, 57. The p-amidinophenylglycine moiety binds into the trypsin primary, specificity pocket, interacting with Asp189. The amide forms a hydrogen, bond to the carbonyl oxygen atom of Ser214. The inhibitor moiety, from the, 113 K structure of trypsin inactivated by the reaction product of, Z-(4-AmPhGly)P(OPh)2, was docked into human thrombin [Bode, W., Mayr, I., Baumann, U., Huber, R., Stone, S. R., & Hofsteenge, J. (1989) EMBO J. 8, 3467-3475] and energy minimized. The inhibitor fits well into the thrombin, active site, forming favorable contacts similar to those in the trypsin, complex with no bad contacts.

About this Structure

1MAY is a Single protein structure of sequence from Bos taurus with CA and ZAP as ligands. Active as Trypsin, with EC number 3.4.21.4 Full crystallographic information is available from OCA.

Reference

Inhibition of trypsin and thrombin by amino(4-amidinophenyl)methanephosphonate diphenyl ester derivatives: X-ray structures and molecular models., Bertrand JA, Oleksyszyn J, Kam CM, Boduszek B, Presnell S, Plaskon RR, Suddath FL, Powers JC, Williams LD, Biochemistry. 1996 Mar 12;35(10):3147-55. PMID:8605148

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