A carlactonoic acid methyltransferase that contributes to the inhibition of shoot branching in Arabidopsis.

SignificanceStrigolactones (SLs) are a group of apocarotenoid hormones, which regulates shoot branching and other diverse developmental processes in plants. The major bioactive form(s) of SLs as endogenous hormones has not yet been clarified. Here, we identify an Arabidopsis methyltransferase, CLAMT, responsible for the conversion of an inactive precursor to a biologically active SL that can interact with the SL receptor in vitro. Reverse genetic analysis showed that this enzyme plays an essential role in inhibiting shoot branching. This mutant also contributed to specifying the SL-related metabolites that could move from root to shoot in grafting experiments. Our work has identified a key enzyme necessary for the production of the bioactive form(s) of SLs.

Quantum Chemical Study of the Cycloaddition Reaction of Tropone with 1,1-Diethoxyethene Catalyzed by B(C6F5)3 or BPh3.

Cycloaddition reaction of tropone with 1,1-diethoxyethene catalyzed by Lewis acid (LA), B(C6F5)3 or BPh3, was examined by using ωB97X-D-level density functional theory (DFT) calculations. In the absence of LA, the reaction proceeds in a stepwise fashion to form two chemical bonds, first between the C2 atom in tropone and the C2 atom in ethene and then between the C5 atom in the former and the C1 atom in the latter. When B(C6F5)3 is attached to the O atom in tropone, the C5 atom in tropone is attacked preferentially by the C1 atom in ethene in the second stage. The attack of the O atom in tropone is shown to be less likely; thus, the [4 + 2] addition is favored in the B(C6F5)3-catalyzed reaction. In contrast, the attack of the O atom in the BPh3-attached tropone to the C1 atom in ethene is preferred over the attack of the C5 atom, indicating that the [8 + 2] cycloaddition instead of the [4 + 2] cycloaddition proceeds in the BPh3-catalyzed reaction. Whether the C1 atom in ethene is attacked by C5 or by O in the second bond formation step is shown in this study to be governed mainly by the nucleophilicity of σ-lone pair electrons of the carbonyl O atom of tropone in the presence of LA. These results are consistent with the experiments reported by Li and Yamamoto.