title: 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) [corrected] 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.
authors.affiliation: a Faculty of Agriculture, Department of Applied Biological Science , Kagawa University , Miki-cho, Kagawa , Japan.
authors.forename: Md Tazul Islam
authors.initials: MT
authors.lastname: Chowdhury
authors.affiliation: a Faculty of Agriculture, Department of Applied Biological Science , Kagawa University , Miki-cho, Kagawa , Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Ando
authors.affiliation: a Faculty of Agriculture, Department of Applied Biological Science , Kagawa University , Miki-cho, Kagawa , Japan.
authors.forename: Ryo C
authors.initials: RC
authors.lastname: Yanagita
authors.affiliation: a Faculty of Agriculture, Department of Applied Biological Science , Kagawa University , Miki-cho, Kagawa , Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Kawanami
mesh_terms: D004952:Esters; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010944:Plants / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D004952:Esters; D005227:Fatty Acids; C002055:allose; D005947:Glucose
keywords: D-allose; inhibitory activity; rare sugar; regioselective transesterification