Fructose-6-phosphate aldolase in organic synthesis:: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays

被引：113

作者：

Castillo, Jose A.

Calveras, Jordi

Casas, Josefina

Mitjans, Montserrat

Vinardell, M. Pilar

Parella, Teodor

Inoue, Tomoyuki

Sprenger, Georg A.

Joglar, Jesus

Clapes, Pere

机构：

[1] CSIC, Inst Chem & Environm Res, IIQAB, Barcelona 08034, Spain

[2] Univ Barcelona, Fac Pharm, Dept Physiol, E-08028 Barcelona, Spain

[3] Univ Autonoma Barcelona, Serv Ressonancia Magnet Nucl, E-08193 Barcelona, Spain

[4] Univ Stuttgart, Inst Microbiol, D-70569 Stuttgart, Germany

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 26期

关键词：

D O I：

10.1021/ol0625482

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

D-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-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, beta-galactosidase and alpha-glucosidase.

引用

页码：6067 / 6070

页数：4

共 34 条

[21] A direct and efficient stereoconservative procedure for the selective oxidation of N-protected β-amino alcohols [J].