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Original scientific paper
https://doi.org/10.5562/cca3579

A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal

Sanja Škulj ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia
Mario Vazdar   ORCID icon orcid.org/0000-0001-6905-6174 ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia

Fulltext: english, pdf (9 MB) pages 229-239 downloads: 243* cite
APA 6th Edition
Škulj, S. & Vazdar, M. (2019). A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal . Croatica Chemica Acta, 92 (2), 229-239. https://doi.org/10.5562/cca3579
MLA 8th Edition
Škulj, Sanja and Mario Vazdar. "A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal ." Croatica Chemica Acta, vol. 92, no. 2, 2019, pp. 229-239. https://doi.org/10.5562/cca3579. Accessed 11 Apr. 2021.
Chicago 17th Edition
Škulj, Sanja and Mario Vazdar. "A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal ." Croatica Chemica Acta 92, no. 2 (2019): 229-239. https://doi.org/10.5562/cca3579
Harvard
Škulj, S., and Vazdar, M. (2019). 'A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal ', Croatica Chemica Acta, 92(2), pp. 229-239. https://doi.org/10.5562/cca3579
Vancouver
Škulj S, Vazdar M. A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal . Croatica Chemica Acta [Internet]. 2019 [cited 2021 April 11];92(2):229-239. https://doi.org/10.5562/cca3579
IEEE
S. Škulj and M. Vazdar, "A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal ", Croatica Chemica Acta, vol.92, no. 2, pp. 229-239, 2019. [Online]. https://doi.org/10.5562/cca3579

Abstracts
In this work, we studied in detail the reaction mechanism of modification of arginine (Arg), cysteine (Cys) and histidine (His) model amino acids upon the reaction with biologically relevant reactive aldehydes 4-hydroxy-2-nonenal (HNE) and 4-oxo-2-nonenal (ONE) in acetonitrile and acetonitrile/water systems by using high level ab initio calculations. We identified and characterized all of the reaction steps along two possible pathways – Michael addition pathway and Schiff base pathway resulting in the formation of Michael adducts/hemiacetals and carbinolamine/Schiff base adducts, depending on the reactive aldehyde and the reaction pathway. Overall energetics suggests that Arg amino acid is more reactive than Cys and His amino acids in both reaction pathways. We established that the ONE is in general more reactive than HNE and also found out that addition of water in the reaction steps involving proton transfer strongly catalyzes the reaction by decreasing prohibitively high free energy barriers.

Creative Commons License This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords
amino acids; 4-hydroxy-2-nonenal; 4-oxo-2-nonenal; quantum chemical calculations; oxidative stress

Hrčak ID: 227005

URI
https://hrcak.srce.hr/227005

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