The required amount of abscisic acid containing 4 – 5 D atoms ([2H]ABA) in the cyclohexene fragment of the molecule was produced via isotope exchange in 100% deuterated D2O at 220°C in the presence of diisopropyl ethylamine. The yield of labeled compound was 45 – 80%. A complex of biological studies was carried out using the D-labeled preparation. It was established that [2H]ABAserved as a growth substrate for soil bacteria, which included the isotopic label in the composition of cell metabolites. The characteristics of D-labeled metabolites allowed their reliable identification in mass spectra of the total bacterial metabolome. Three intermediates of a new metabolic pathway of microbial degradation of this phytohormone were identified using the developed technique.
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Acknowledgments
The work was performed according to a planned State Task, State Reg. No. AAAA-A19-119022590101-1 on the topic Study of the Structure and Function of Natural Peptides to Create New Drugs, Structure Optimization of Candidate Peptides, Development of Synthetic Schemes, Including Preparation of Deuterium- and Tritium-Labeled Physiological Active Compounds. The drug testing part of the work was supported by RSF Grant No. 17-14-01363. The participation of Yu. V. Gogolev, N. E. Gogoleva, and T. A. Konnova was included in the framework of a State Task for FRC KazSC RAS using equipment of the CCU SAC FRC KazSC RAS. The participation of T. S. Yermekkaliyev was supported by Biomarker SRL [K(VR)FU]. Mass spectra were obtained by A. D. Misharev at the resource center Methods of Analysis of Compound Compositions, St. Petersburg State University.
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 55, No. 7, pp. 60 – 64, July, 2021.
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Yermekkaliyev, T.S., Gogoleva, N.E., Gogolev, Y.V. et al. Metabolism by Rhizobacteria of Abscisic Acid Deuterated in the Cyclohexene Part. Pharm Chem J 55, 745–749 (2021). https://doi.org/10.1007/s11094-021-02487-w
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DOI: https://doi.org/10.1007/s11094-021-02487-w