CRYSTAL STRUCTURE OF S. MARCESCENS CHITINASE B IN COMPLEX WITH THE CYCLIC DIPEPTIDE INHIBITOR CYCLO-(HIS-L-PRO) AT 1.9 A RESOLUTION

File:1w1t.gif


1w1t, resolution 1.90Å

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OverviewOverview

Family 18 chitinases play an essential role in a range of pathogens and, pests. Several inhibitors are known, including the potent inhibitors, argadin and allosamidin, and the structures of these in complex with, chitinases have been elucidated. Recent structural analysis has revealed, that CI-4 [cyclo-(L-Arg-D-Pro)] inhibits family 18 chitinases by mimicking, the structure of the proposed reaction intermediate. Here we report the, high-resolution structures of four new CI-4 derivatives, cyclo-(L-Arg-L-Pro), cyclo-(Gly-L-Pro), cyclo-(L-His-L-Pro), and, cyclo-(L-Tyr-L-Pro), in complex with a family 18 chitinase. In addition, details of enzyme inhibition and in vivo activity against Saccharomyces, cerevisiae are presented. The structures reveal that the common, cyclo-(Gly-Pro) substructure is sufficient for binding, allowing, modification of the side chain of the nonproline residue. This suggests, that design of cyclic dipeptides with a view to increasing inhibition of, family 18 chitinases should be possible through relatively accessible, chemistry. The derivatives presented here in complex with chitinase B from, Serratia marcescens provide further insight into the mechanism of, inhibition of chitinases by cyclic dipeptides as well as providing a new, scaffold for chitinase inhibitor design.

About this StructureAbout this Structure

1W1T is a Single protein structure of sequence from Serratia marcescens with SO4, CHQ and GOL as ligands. Active as Chitinase, with EC number 3.2.1.14 Known structural/functional Site: . Full crystallographic information is available from OCA.

ReferenceReference

Structure-based exploration of cyclic dipeptide chitinase inhibitors., Houston DR, Synstad B, Eijsink VG, Stark MJ, Eggleston IM, van Aalten DM, J Med Chem. 2004 Nov 4;47(23):5713-20. PMID:15509170

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