Total synthesis of naturally occurring casuarine (1) and the first total synthesis of casuarine 6-O-alpha-glucoside (2) were achieved through complete stereoselective nitrone cycloaddition, Tamao–Fleming oxidation and selective a-glucosylation as key steps. Biological assays of the two compounds proved their strong and selective inhibitory properties towards glucoamylase NtMGAM and trehalase Tre37A, respectively, which place them among the most powerful inhibitors of these enzymes. The structural determination of the complexes of NtMGAM with 1 and of Tre37A with 2 revealed interesting similarities in the catalytic sites of these two enzymes which belong to different families and clans.

Total Syntheses of Casuarine and its 6-O-alpha-Glucoside: Complementary Inhibition towards Glycoside Hydrolases of Families GH31 and GH37 / F. CARDONA; C. PARMEGGIANI; E. FAGGI; C. BONACCINi; P. GRATTERI; L. SIM; T. GLOSTER; S. ROBERTS; G. DAVIES; D. ROSE; A. GOTI. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - STAMPA. - 15:(2009), pp. 1627-1636. [10.1002/chem.200801578]

Total Syntheses of Casuarine and its 6-O-alpha-Glucoside: Complementary Inhibition towards Glycoside Hydrolases of Families GH31 and GH37

CARDONA, FRANCESCA;PARMEGGIANI, CAMILLA;FAGGI, ENRICO;BONACCINI, CLAUDIA;GRATTERI, PAOLA;GOTI, ANDREA
2009

Abstract

Total synthesis of naturally occurring casuarine (1) and the first total synthesis of casuarine 6-O-alpha-glucoside (2) were achieved through complete stereoselective nitrone cycloaddition, Tamao–Fleming oxidation and selective a-glucosylation as key steps. Biological assays of the two compounds proved their strong and selective inhibitory properties towards glucoamylase NtMGAM and trehalase Tre37A, respectively, which place them among the most powerful inhibitors of these enzymes. The structural determination of the complexes of NtMGAM with 1 and of Tre37A with 2 revealed interesting similarities in the catalytic sites of these two enzymes which belong to different families and clans.
2009
15
1627
1636
F. CARDONA; C. PARMEGGIANI; E. FAGGI; C. BONACCINi; P. GRATTERI; L. SIM; T. GLOSTER; S. ROBERTS; G. DAVIES; D. ROSE; A. GOTI
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/332232
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