Synthesis of naturally occurring β-l-arabinofuranosyl-l-arabinofuranoside structures towards the substrate specificity evaluation of β-l-arabinofuranosidase
Synthesis of naturally occurring β-l-arabinofuranosyl-l-arabinofuranoside structures towards the substrate specificity evaluation of β-l-arabinofuranosidase
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天然存在的 β-l-阿拉伯呋喃糖基-l-阿拉伯呋喃糖苷结构的合成，用于评估 β-l-阿拉伯呋喃糖苷酶的底物特异性
DOI：
10.1016/j.bmc.2022.116849
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发表时间：
2022
影响因子：
3.5
通讯作者：
Ito Yukishige
中科院分区：
文献类型：
--
作者：
Ishiwata Akihiro;Fujita Kiyotaka;Fushinobu Shinya;Tanaka Katsunori;Ito Yukishige
通过2-萘甲醚介导的分子内糖苷配基传递（NAP-IAD）立体选择性地合成了β-l-阿拉伯呋喃糖基-（1 → 2）-、-（1 → 3）-和-（1 → 5）-α-l-阿拉伯呋喃糖苷甲基酯。将NAP-IAD方法简单地扩展用于合成具有β-l-阿拉伯呋喃糖基-（1 → 5）-l-阿拉伯呋喃糖基非还原末端结构的三糖基序，其中支链β-l-阿拉伯呋喃糖基-（1 → 5）-[α-l-阿拉伯呋喃糖基-（1 → 3）]-α-l-阿拉伯呋喃糖基和线性β-l-阿拉伯呋喃糖基-（1 → 5）-β-l-阿拉伯呋喃糖基-（1 → 5）-β-l-阿拉伯呋喃糖基。阿拉伯呋喃糖基结构，分别在橄榄阿拉伯聚糖和甲藻聚醚。利用区域异构体对双歧杆菌β-l-阿拉伯呋喃糖苷酶HypBA 1的底物特异性进行研究的结果表明，HypBA 1可以水解所有三个键，但对β-（1 → 5）-连接二糖的活性明显低于其他两个区域异构体，包括拟议的天然降解产物，来自植物胞外基质的β-（1 → 2）-连接二糖，如extensin。另一方面，发现黄单胞菌XeHypBA 1水解所有三种二糖作为底物，对β-（1 → 2）-键的特异性高于双歧杆菌HypBA 1。
Methyl β-l-arabinofuranosyl-(1 → 2)-, -(1 → 3)-, and -(1 → 5)-α-l-arabinofuranosides have been stereoselectively synthesized through 2-naphthylmethyl ether-mediated intramolecular aglycon delivery (NAP-IAD), whose β-linkages were confirmed by NMR analysis on the3JH1–H2coupling constant and13C chemical shift of C1. The NAP-IAD approach was simply extended for the synthesis of trisaccharide motifs possessing β-l-arabinofuranosyl-(1 → 5)-l-arabinofuranosyl non-reducing terminal structure with the branched β-l-arabinofuranosyl-(1 → 5)-[α-l-arabinofuranosyl-(1 → 3)]-α-l-arabinofuranosyl and the liner β-l-arabinofuranosyl-(1 → 5)-β-l-arabinofuranosyl-(1 → 5)-β-l-arabinofuranosyl structures in olive arabinan and dinoflagellate polyethers, respectively. The results on the substrate specificity of a bifidobacterial β-l-arabinofuranosidase HypBA1 using the regioisomers indicated that HypBA1 could hydrolyze all three linkages however behaved clearly less active to β-(1 → 5)-linked disaccharide than other two regioisomers including the proposed natural degradation product, β-(1 → 2)-linked one from plant extracellular matrix such as extensin. On the other hand,XanthomonasXeHypBA1 was found to hydrolyze all three disaccharides as the substrate with higher specificity to β-(1 → 2)-linkage than bifidobacterial HypBA1.