Synthesis of trehazolin analogues containing modified sugar moieties

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Abstract
In order to elucidate the biological roles of the sugar moiety of the trehalase inhibitor trehazolin 1, the sugar portion was first replaced with hydrophobic aromatic functions, providing the N-phenyl 3 and N-benzyl derivatives 4 of trehazolin 1. Then the six analogues with the sugar moiety being replaced with D-mannopyranose 5, 3-deoxy-ribo-hexopyranose 6, D-galactopyranose 7, 6-deoxy-D-glucopyranose 8, 5a-carba-α-D-glucopyranose 9 and 5a-carba-α-D-xylo-hex-5(5a)-enopyranose residues 10 were synthesized. In the hope of improving the fungicidal activity of trehazolin 1, we prepared two disaccharide analogues, 11 and 12, containing maltose and cellobiose residues. A remarkable decrease in potency was observed in the analogues 5–8 and 10, but not for 5a′-carbatrehazolin 9, suggesting an essential role for the D-gluco configuration of the hexopyranose portion. The β-D-glucosyl analogue 12 showed an increase in antifungal activity against Rhizoctonia solani, as compared with that of trehazolin 1. The analogues 3 and 4 were not trehalase inhibitors, but rather were moderate α-glucosidase inhibitors.

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