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Glycosylated cyclophellitol-derived activity-based probes and inhibitors for cellulases
RSC Chemical Biology ( IF 4.2 ) Pub Date : 2020-07-28 , DOI: 10.1039/d0cb00045k
Casper de Boer 1 , Nicholas G S McGregor 2 , Evert Peterse 1 , Sybrin P Schröder 1 , Bogdan I Florea 1 , Jianbing Jiang 1 , Jos Reijngoud 3 , Arthur F J Ram 3 , Gilles P van Wezel 3 , Gijsbert A van der Marel 1 , Jeroen D C Codée 1 , Herman S Overkleeft 1 , Gideon J Davies 2
Affiliation  

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.

中文翻译:

糖基化环苯醇衍生的基于活性的纤维素酶探针和抑制剂

纤维素酶和相关的 β-1,4-葡聚糖酶是木质纤维素降解酶混合物的重要组成部分。β-1,4-葡聚糖酶活性的检测通常依赖于监测纯化的木质纤维素衍生底物或合成显色底物的分解,这限制了可检测的活性,并使追踪复杂酶混合物中特定成分的活性变得复杂。作为快速检测和鉴定β-1,4-葡聚糖酶的工具,我们合成了一系列模仿β-1,4-葡聚糖寡糖的糖基化环苯乙醇抑制剂。这些化合物是 HiCel7B(一种著名的 GH7内切-β-1,4-葡聚糖酶)的高效抑制剂。精心设计的基于活性的探针有助于直接检测和鉴定复杂真菌分泌组中的 β-1,4-葡聚糖酶,且与 β- D-葡萄糖苷酶没有任何可检测到的交叉反应性。这些探针和抑制剂为不断增长的环杓醇衍生探针工具箱增添了宝贵的新能力,用于基于活性的生物质降解酶分析。
更新日期:2020-08-06
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