Fructose-6-phosphate Aldolase in Organic Synthesis: Preparation of D-Fagomine, N-Alkylated Derivatives, and Preliminary Biological Assays

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• 作者：Jos&eacute ; A. Castillo ; Jordi Calveras ; Josefina Casas ; Montserrat Mitjans ; M. Pilar Vinardell ; Teodor Parella ; Tomoyuki Inoue ; Georg A. Sprenger ; Jesú ; s Joglar ; Pere Clap&eacute ; s
• 刊名：Organic Letters
• 出版年：2006
• 出版时间：December 21, 2006
• 年：2006
• 卷：8
• 期：26
• 页码：6067 - 6070
• 全文大小：67K
• 年卷期：v.8,no.26(December 21, 2006)
• ISSN：1523-7052

文摘

D-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of itsN-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA)to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters.Some N-alkyl derivatives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against-galactosidase and -glucosidase.