Syntheses and biological activities of deoxy-d-allose fatty acid ester analogs

Abstract

We describe the syntheses of three different deoxy-D-allose analogs [2-deoxy-D-allose (2-DOAll), 1,2-dideoxy-D-allose (1,2-DOAll), and 1,2-didehydro-1,2-dideoxy-D-allose (1,2-DHAll)] and their fatty acid esters via regioselective lipase-catalyzed transesterification. Among them, 2-DOAll and its decanoate (2-DOAll-C10) showed higher inhibitory activity on plant growth, which is similar to D-allose (All) and its decanoate (All-C10). Bioassay results of deoxy-All-C10 on four plant species suggest that the hydroxy group at the C-1 position might be important showing growth inhibitory activity. In addition, co-addition of gibberellin (GA₃) with 1,2-DHAll-C10 and 2-DOAll-C10 recovered plant growth, suggesting that they might mainly inhibit biosynthesis of gibberellin.

Graphical abstract

Biological activities of three different deoxy allose esters and allose ester on the shoots of lettuce.

Key words:

• rare sugar
• D-allose
• regioselective transesterification
• inhibitory activity

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Erratum

Acknowledgments

The first author is grateful to the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan for providing financial support.