Synthesis of naturally occurring β-D-glucopyranoside based on enzymatic β-glycosidation
Synthesis of naturally occurring β-D-glucopyranoside based on enzymatic β-glycosidation
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DOI：
10.1016/j.molcatb.2006.01.031
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发表时间：
2006-05-19
影响因子：
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通讯作者：
Kato, K
中科院分区：
文献类型：
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作者：
Akita, H;Kawahara, E;Kato, K
为了合成天然存在的β-D-吡喃葡萄糖苷，在D-葡萄糖存在下，使用来自杏仁的天然或固定化β-葡萄糖苷酶(EC 3.2.1.21)在平衡条件下对七种官能化伯醇进行直接β-糖苷化。使用高浓度的醇受体3-甲基-2-丁烯-1-醇(3)或2-甲基-2-丙烯-1-醇(4)和固定化酶分别产生相应的β-D-吡喃葡萄糖苷(21，天然产物)或(22)，产率分别为65%或51%。另一方面，使用固定化酶在 90% 叔丁醇/H2O 溶液中使用 4 当量的官能化醇 (5-9)，分别以中等产率提供天然存在的 β-D-吡喃葡萄糖苷 (23-27)。其中，5种β-D-吡喃葡萄糖苷（21、22、24、25和27）分别转化为氰基葡萄糖苷（红氰苷A（28）、osmaronin（29））和其他天然存在的β-D-吡喃葡萄糖苷（30-32）。 (c) 2006 Elsevier B.V. 保留所有权利。
For the purpose of synthesis of naturally occurring beta-D-glucopyranoside, direct beta-glycosidation for seven kinds of the functionalized primary alcohol in the presence of D-glucose using native or immobilized beta-glucosidase (EC 3.2.1.21) from almonds under equilibrium condition was carried out. The utilization of high concentration of the alcohol acceptor, 3-methyl-2-buten-1-ol (3) or 2-methyl-2-propen-1-ol (4) using the immobilized enzyme gave the corresponding beta-D-glucopyranoside (21, natural product) or (22) in 65 or 51% yield, respectively. On the other hand, the utilization of 4-equivalents of the functionalized alcohols (5-9) using the immobilized enzyme in 90% tert-butanol/H2O Solution afforded the naturally occurring beta-D-glucopyranosides (23-27), respectively, in moderate yield. Among them, five kinds of beta-D-glucopyranosides (21, 22, 24, 25, and 27) were converted into the cyanoglucosides (rhodiocyanoside A (28), osmaronin (29)) and other naturally occurring beta-D-glucopyranosides (30-32), respectively. (c) 2006 Elsevier B.V. All rights reserved.