Analysis of the structure and substrate scope of chitooligosaccharide oxidase reveals high affinity for C2‐modified glucosamines,FEBS Letters

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Analysis of the structure and substrate scope of chitooligosaccharide oxidase reveals high affinity for C2‐modified glucosamines
FEBS Letters ( IF 3.0 ) Pub Date : 2020-06-18 , DOI: 10.1002/1873-3468.13854
Simone Savino ₁ , Sonja Jensen ₁ , Anke Terwisscha van Scheltinga ₁ , Marco W Fraaije ₁

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Chitooligosaccharide oxidase (ChitO) is a fungal carbohydrate oxidase containing a bicovalently bound FAD cofactor. The enzyme is known to catalyse the oxidation of chitooligosaccharides, oligomers of N‐acetylated glucosamines derived from chitin degradation. In this study, the unique substrate acceptance was explored by testing a range of N‐acetyl‐d‐glucosamine derivatives, revealing that ChitO preferentially accepts carbohydrates with a hydrophobic group attached to C2. The enzyme also accepts streptozotocin, a natural product used to treat tumours. Elucidation of the crystal structure provides an explanation for the high affinity towards C2‐decorated glucosamines: the active site has a secondary binding pocket that accommodates groups attached at C2. Docking simulations are fully in line with the observed substrate preference. This work expands the knowledge on this versatile enzyme.

中文翻译：

壳寡糖氧化酶的结构和底物范围分析表明对 C2 修饰的葡糖胺具有高亲和力

壳寡糖氧化酶 (ChitO) 是一种真菌碳水化合物氧化酶，含有双价结合的 FAD 辅因子。已知该酶催化壳寡糖的氧化，壳寡糖是源自几丁质降解的 N-乙酰化葡糖胺的低聚物。在这项研究中，通过测试一系列 N-乙酰-d-葡糖胺衍生物探索了独特的底物接受性，揭示了 ChitO 优先接受带有连接到 C2 的疏水基团的碳水化合物。该酶还接受链脲佐菌素，一种用于治疗肿瘤的天然产物。晶体结构的阐明为对 C2 修饰的葡糖胺的高亲和力提供了解释：活性位点有一个二级结合口袋，可容纳连接在 C2 上的基团。对接模拟完全符合观察到的基材偏好。

更新日期：2020-06-18

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