Determination of absolute configuration of dihydroindenols by enzymatic analysis and chiral HPLC
DOI:
https://doi.org/10.15407/dopovidi2022.04.077Keywords:
enzymatic deracemization, Burkholderia cepacia lipase, absolute configuration, Kazlauskas rule, chiral HPLCAbstract
Racemic 1,2-dihydroindenols were resolved into enantiomers using kinetically controlled esterification in the presence of Burkholderia cepacia lipase (BCL) biocatalyst. The resolution of halodihydroindenol acetates to enantiomers by enzymatic hydrolysis in the presence of Candida Antarctica B lipases immobilized on diatomite was also studied. To determine the absolute configuration of stereoisomers of halodihydroindenols, chiral HPLC analysis was used in combination with enzymatic analysis. The combined use of several methods increases the reliability in determining the absolute configuration of the studied compounds.
Downloads
References
Rousse, l C., Del Rio, A., Pierrot-Sanders, J., Piras, P. & Vanthuyne, N. (2004). Chiral liquid chromatography contribution to the determination of the absolute configuration of enantiomers. J. Chromatogr. A, 1037, pp. 311-328. https: //doi. org/10.1016/j. chroma. 2004. 01. 065
Liu, F., Boross, P. I., Wang, Y. -F., Tozser, J., Louis, J. M., Harrison, R. W. & Weber, I. T. (2005). Kinetic, stability, and structural changes in high-resolution crystal structures of HIV-1 protease with drug-resistant mutations L24I, I50V, and G73S. J. Mol. Biol., 354, pp. 789-800. https: //doi. org/10. 1016/j. jmb. 2005. 09. 095
Shankar, S. S., Dubé, M. P., Gorski, J. C., Klaunig, J. E. & Steinberg, H. O. (2005). Indinavir impairs endothelial function in healthy HIV-negative men. Am. Heart J., 150, pp. 933. https: //doi. org/10.1016/j. ahj. 2005. 06. 005
Igarashi, Y., Otsutomo, S., Harada, M. & Nakano, S. (1997). Enzymatic resolution of indene bromohydrin acetate using immobilized lipase. Tetrahedron: Asymmetry, 8, pp. 2833-2837. https: //doi. org/10. 1016/S0957-4166(97)00351-0
Weinstock, M., Luques, L., Bejar, C. & Shoham, S. (2006). Ladostigil, a novel multifunctional drug for the treatment of dementia co-morbid with depression. J. Neural Transm., Suppl. 70, pp. 443-446. https: //doi. org/10.1007/978-3-211-45295-0_67
Prysiazhnuk, D. V., Kolodiazhna, О. О. & Kolodiazhnyi, O. I. (2020). Enzymatic deracemization of halogenated dihydroindenols and dihydroindenediols substituted in benzene ring. Dopov. Nac. akad. nauk Ukr., No. 3, pp. 71-81. https: //doi.org/10. 15407/dopovidi2020. 03. 071
Kišić, A., Stephan, M. & Mohar, B. (2015). ansa-Ruthenium(II) complexes of R2NSO2DPEN-(CH2)n(η6-aryl) conjugate ligands for asymmetric transfer hydrogenation of aryl ketones. Adv. Synth. Catal., 357, pp. 2540- 2546. https: //doi.org/10.1002/adsc.201500288
Yoshimatsu, S., Yamada, A. & Nakata, K. (2018). Silylative kinetic resolution of racemic 1-indanol derivatives catalyzed by chiral guanidine. J. Org. Chem., 83, pp. 452-458. https: //doi.org/10.1021/acs. joc. 7b02493
Falconnet, A., Magre, M., Maity, B., Cavallo, L. & Rueping, M. (2019). Asymmetric magnesium-catalyzed hydroboration by metal-ligand cooperative catalysis. Angew. Chem., 58, pp. 17567-17571. https: //doi. org/10.1002/anie.201908012
FDA’s policy statement for the development of new stereoisomeric drugs. (1992). Chirality, 4, pp. 338-340. https: //doi. org/10.1002/chir.530040513
Lough, W. J. (Ed. ). (1989). Chiral liquid chromatography. New York: Blackie/Chapman and Hall.
Pirkle, W. H. & Pochapsky, T. C. (1989). Considerations of chiral recognition relevant to the liquid chromatography separation of enantiomers. Chem. Rev., 89, pp. 347-362. https: //doi.org/10.1021/cr00092a006
Kazlauskas, R. J., Weissfloch, A. N. E., Rappaport, A. T. & Cuccia, L. A. (1991). A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J. Org. Chem., 56, pp. 2656-2665. https: //doi. org/10.1021/jo00008a016
Prysiazhnuk, D. V., Rusanov, E. B. & Kolodiazhnyi, O. I. (2021). The absolute configu-ration of 2-bromo-2, 3- dihydro-1H-inden-1-ols. Synth. Commun., 51, pp. 3023-3031. https: //doi.org/10.1080/00397911.2021.1960378
Seco, J. M., Quiñoá, E. & Riguera, R. (2004). The assignment of absolute configuration by NMR. Chem. Rev., 104, 17-117. https: //doi.org/10.1021/cr000665j
Kolodiazhna, O. O., Prysiazhnuk, D. V., Kolodiazhna, A. O. & Kolodiazhnyi, O. I. (2022). Synthesis of optically active vicinal fluorocyclopentanols and fluorocyclopentanamines by enzymatic deracemization. Arkivoc, 3, pp. 14-26. https: //doi.org/10.24820/ark. 5550190. p011.634
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2022 Reports of the National Academy of Sciences of Ukraine
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.