Design and chemoenzymatic synthesis of thiooligosaccharide inhibitors of 1,3:1,4-beta-D-glucanases
Design and chemoenzymatic synthesis of thiooligosaccharide inhibitors of 1,3:1,4-beta-D-glucanases
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DOI：
10.1016/s0968-0896(96)00166-6
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发表时间：
1996-11-01
影响因子：
3.5
通讯作者：
Driguez, H
中科院分区：
文献类型：
--
作者：
Moreau, V;Viladot, JL;Driguez, H
描述了一种成功的化学酶促合成作为1，3：1，4-β-D-葡聚糖酶抑制剂的具有糖苷间硫原子的寡糖。关键化合物3a由乙酰化的1-硫代-β-昆布二糖4和甲基4 '-O-三氟甲磺酰基-乳糖苷5合成。脱-O-酰化后，在由来自热纤梭菌的纤维糊精磷酸化酶催化的磷酸化延伸中，四糖3b用作受体，葡萄糖-I-P用作供体。分离出预期的五糖2a和六糖1，产率分别为56%和13%。如所预期的，硫代寡糖1、2a和3b对分离自地衣芽孢杆菌的1，3：1，4-β-D-葡聚糖酶的酶裂解具有抗性。此外，它们已显示出作为该酶水解发色三糖底物11的竞争性抑制剂。版权所有（C）1996 Elsevier Science Ltd
A successful chemoenzymatic synthesis of oligosaccharides with an interglucosidic sulfur atom as inhibitors of 1,3: 1,4-beta-D-glucanases is described. The key compound 3a was synthesized from acetylated 1-thio-beta-laminaribiose 4 and the methyl 4'-O-triflyl-lactoside 5. After de-O-acylation, the tetrasaccharide 3b was used as an acceptor and glucose-l-P as a donor in a phosphorolytic elongation catalysed by cellodextrin phosphorylase from Clostridium thermocellum. The expected pentasaccharide 2a and hexasaccharide 1 were isolated in 56% and 13% yield, respectively. As expected, the thiooligosaccharides 1, 2a, and 3b were resistant to enzymatic cleavage by 1,3:1,4-beta-D-glucanase isolated from Bacillus licheniformis. Furthermore, they have been shown to act as competitive inhibitors of the hydrolysis of the chromophoric trisaccharide substrate 11 by this enzyme. Copyright (C) 1996 Elsevier Science Ltd