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Glycosylated cyclophellitol-derived activity-based probes and inhibitors for cellulases
Authors:
Casper
De Boer
(Leiden University)
,
Nicholas G. S.
Mcgregor
(The University of York)
,
Evert
Peterse
(Leiden University)
,
Sybrin P.
Schröder
(Leiden University)
,
Bogdan I.
Florea
(Leiden University)
,
Jianbing
Jiang
(Leiden University)
,
Jos
Reijngoud
(Leiden University)
,
Arthur F. J.
Ram
(Leiden University)
,
Gilles P.
Van Wezel
(Leiden University)
,
Gijsbert A.
Van Der Marel
(Leiden University)
,
Jeroen D. C.
Codée
(Leiden University)
,
Herman S.
Overkleeft
(Leiden University)
,
Gideon
Davies
(The University of York)
Co-authored by industrial partner:
No
Type:
Journal Paper
Journal:
Rsc Chemical Biology
, VOL 25
State:
Published (Approved)
Published:
July 2020
Diamond Proposal Number(s):
18598

Abstract: Cellulases and related β-1,4-glucanases are essential components of lignocellulose-degrading enzyme mixtures. The detection of β-1,4-glucanase activity typically relies on monitoring the breakdown of purified lignocellulose-derived substrates or synthetic chromogenic substrates, limiting the activities which can be detected and complicating the tracing of activity back to specific components within complex enzyme mixtures. As a tool for the rapid detection and identification of β-1,4-glucanases, a series of glycosylated cyclophellitol inhibitors mimicking β-1,4-glucan oligosaccharides have been synthesised. These compounds are highly efficient inhibitors of HiCel7B, a well-known GH7 endo-β-1,4-glucanase. An elaborated activity-based probe facilitated the direct detection and identification of β-1,4-glucanases within a complex fungal secretome without any detectable cross-reactivity with β-D-glucosidases. These probes and inhibitors add valuable new capacity to the growing toolbox of cyclophellitol-derived probes for the activity-based profiling of biomass-degrading enzymes.
Subject Areas:
Chemistry,
Biology and Bio-materials
Instruments:
I03-Macromolecular Crystallography
Documents:
d0cb00045k.pdf