HO● ‐ initiated oxidation of isoleucine amino acid in the aqueous phase

Protein damage by the direct oxidative attack on amino acid side chains is considered the main cause of human aging and diseases. Therefore, a better understanding of the oxidation process is necessary for screening and designing new drugs. In this work, the oxidation of L‐isoleucine (Ile) by HO● ra...

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Bibliographic Details
Published in:Vietnam journal of chemistry 2023-07, Vol.61 (S1), p.37-44
Main Authors: Lan, Nguyen Thi Huong, Hieu, Truong Dinh, Chinh, Ngo Thi, Le Anh, Nguyen Thi, Nhi, Pham Thi Yen, Quang, Dao Duy
Format: Article
Language:English
Subjects:
Amino acid
DFT
free radical
hydrogen transfer
kinetics
oxidation
SET
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Summary:Protein damage by the direct oxidative attack on amino acid side chains is considered the main cause of human aging and diseases. Therefore, a better understanding of the oxidation process is necessary for screening and designing new drugs. In this work, the oxidation of L‐isoleucine (Ile) by HO● radical was mechanistically and kinetically studied using M05‐2X/6‐311++G(3df,3pd)//M05‐2X/6‐311++G(d,p) level of theory. All possible hydrogen transfer (HT) and single electron transfer (SET) reactions are considered in the aqueous phase. The results showed that the overall diffusion‐controlled rate constant is equal to 4.82×109 M‐1s‐1 at 298.15K. The zwitterionic form is the main existing form that plays an essential role in the HO● ‐ initiated oxidation of Ile (99.98%). The most preponderant reactions are found at C6‐H (36.19%) and C8‐H (37.77%) positions. Finally, the influence of temperature on the overall rate is also evaluated.
ISSN:0866-7144
2572-8288
2572-8288
DOI:10.1002/vjch.202200210