Alves, M. José

Duarte, Vera C. M.

Fortes, A. Gil

Martins, J. A. R.

Mendes, Raquel

Micaelo, N. M.

Universidade do Minho: RepositoriUM

Chemoenzymatic Synthesis of 1-Azafagomine Analogues  R. Mendes, Vera C. M. Duarte, A. Gil Fortes, M. J. Alves, J. A. Martins, N. M. Micaelo University of Minho, Chemistry Research Centre, Campus de Gualtar, 4700-057, Braga, Portugal  tec.raquelmendes@gmail.com  The synthesis of cycloadduct 1 is described in the literature in 87 % yield [1]. The kinetic enzymatic resolution of adduct 1 leads to both enantiomers (+)-1 and (-)-1 in high enantiomeric excess (> 96 % ee) according to scheme 1. [1] NN NOOPhOHNN NOOPhOAc+NN NOOPhOH(+)-1NN NOOPhOH(-)-1Lipase Rvinyl acetate     25 ºC(+)-1Scheme 1  NNNOORa R= C6H5 (PTAD)b R = p-NO2C6H4c R = CH2-p-FC6H4d R = p-CNC6H4Figure 12  In this work this methodology is applied to analogues of PTAD 2b-d (Figure 1). The interest of this structural modification is based on molecular modelling studies, which predicted a higher inhibitory activity for the final products due to the possibility of forming extra hydrogen bonds. The homochiral 1-azafagomine analogues will be evaluated as α- and β-glycosidases; the type of inhibition and the inhibition constants (Ki) will be determined for all compounds.  Acknowledgements: The authors thank to FCT (PTDC/QUI/67407/2006), QREN, COMPETE and POPH for financial support and to the Portuguese NMR Network RNRMN (Bruker Avance II 400). V.C.M.D. also thanks for a PhD grant (SFRH/BD/61290/2009).  References: [1] X. Liang, M. Bols J. Org. Chem. 64, 1999, 8485-8488.  

Chemoenzymatic synthesis of 1-azafagomine analogues

http://repositorium.sdum.uminho.pt/bitstream/1822/15128/1/Raquel%2bVera-Abstract.pdf

Chemoenzymatic synthesis of 1-azafagomine analogues

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Universidade do Minho: RepositoriUM

Universidade do Minho: RepositoriUM