Sulfation of Phenolic Acids: Chemoenzymatic vs. Chemical Synthesis

0566367 - MBÚ 2023 RIV CH eng J - Článek v odborném periodiku
Kolaříková, Viola - Brodsky, Katerina - Petrásková, Lucie - Pelantová, Helena - Cvačka, Josef - Havlíček, Libor - Křen, Vladimír - Valentová, Kateřina
Sulfation of Phenolic Acids: Chemoenzymatic vs. Chemical Synthesis.
International Journal of Molecular Sciences. Roč. 23, č. 23 (2022), č. článku 15171. E-ISSN 1422-0067
Grant CEP: GA ČR(CZ) GA19-00043S; GA MZd(CZ) NU21-02-00135
Institucionální podpora: RVO:61388971 ; RVO:61388963 ; RVO:61389030
Klíčová slova: sulfation * phenolic acids * aryl sulfotransferase * flavonoid metabolites * biotransformation
Obor OECD: Organic chemistry; Analytical chemistry (UOCHB-X); Organic chemistry (UEB-Q)
Impakt faktor: 5.6, rok: 2022
Způsob publikování: Open access
https://www.mdpi.com/1422-0067/23/23/15171

Phenolic acids are known flavonoid metabolites, which typically undergo bioconjugation during phase II of biotransformation, forming sulfates, along with other conjugates. Sulfated derivatives of phenolic acids can be synthesized by two approaches: chemoenzymatically by 3 '-phosphoadenosine-5 '-phosphosulfate (PAPS)-dependent sulfotransferases or PAPS-independent aryl sulfotransferases such as those from Desulfitobacterium hafniense, or chemically using SO3 complexes. Both approaches were tested with six selected phenolic acids (2-hydroxyphenylacetic acid (2-HPA), 3-hydroxyphenylacetic acid (3-HPA), 4-hydroxyphenylacetic acid (4-HPA), 3,4-dihydroxyphenylacetic acid (DHPA), 3-(4-hydroxyphenyl)propionic acid (4-HPP), and 3,4-dihydroxyphenylpropionic acid (DHPP)) to create a library of sulfated metabolites of phenolic acids. The sulfates of 3-HPA, 4-HPA, 4-HPP, DHPA, and DHPP were all obtained by the methods of chemical synthesis. In contrast, the enzymatic sulfation of monohydroxyphenolic acids failed probably due to enzyme inhibition, whereas the same reaction was successful for dihydroxyphenolic acids (DHPA and DHPP). Special attention was also paid to the counterions of the sulfates, a topic often poorly reported in synthetic works. The products obtained will serve as authentic analytical standards in metabolic studies and to determine their biological activity.
Trvalý link: https://hdl.handle.net/11104/0337718