Abstract
Nitrated fatty acids (NO2-FAs) exhibit a variety of important biological attributes, including a nitric oxide (˙NO) donor and a cell-signaling molecule. We investigated the mechanisms of fatty-acid nitration, and the release of ˙NO from NO2-FAs. NO2-FAs are formed effectively by the addition of ˙NO2, followed by either hydrogen abstraction or addition of a second NO2. The latter reaction results in a vicinal nitronitrite ester form of FA, which isomerizes into vicinal nitrohydroxy FA via hydronium ion catalysis. The nitrohydroxy FAs exist in equilibria with NO2-FAs. Nitration of conjugated linoleic acid (cLA) was proved to be significantly more efficient than that of LA. In a nonaqueous environment, release of ˙NO from nitrite ester (ONO-FA) was facilitated by ˙NO2. Furthermore, the release of ˙NO from NO2-cLA is the most favorable in the nitrite ester mechanism. In an aqueous environment, the modified Nef reaction was shown to be feasible. In addition, the release of ˙NO from 10- and 12-NO2-LA involves a larger reaction barrier and is more endergonic than those from 9- and 13-NO2-LA.
| Original language | English |
|---|---|
| Pages (from-to) | 41-48 |
| Number of pages | 8 |
| Journal | Journal of the Chinese Chemical Society |
| Volume | 66 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2019 Jan 1 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
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Release of nitric oxide from nitrated fatty acids : Insights from computational chemistry. / Su, Yi Hsin; Wu, Shih Sheng; Hu, Ching-Han.
In: Journal of the Chinese Chemical Society, Vol. 66, No. 1, 01.01.2019, p. 41-48.Research output: Contribution to journal › Article
TY - JOUR
T1 - Release of nitric oxide from nitrated fatty acids
T2 - Insights from computational chemistry
AU - Su, Yi Hsin
AU - Wu, Shih Sheng
AU - Hu, Ching-Han
PY - 2019/1/1
Y1 - 2019/1/1
N2 - Nitrated fatty acids (NO2-FAs) exhibit a variety of important biological attributes, including a nitric oxide (˙NO) donor and a cell-signaling molecule. We investigated the mechanisms of fatty-acid nitration, and the release of ˙NO from NO2-FAs. NO2-FAs are formed effectively by the addition of ˙NO2, followed by either hydrogen abstraction or addition of a second NO2. The latter reaction results in a vicinal nitronitrite ester form of FA, which isomerizes into vicinal nitrohydroxy FA via hydronium ion catalysis. The nitrohydroxy FAs exist in equilibria with NO2-FAs. Nitration of conjugated linoleic acid (cLA) was proved to be significantly more efficient than that of LA. In a nonaqueous environment, release of ˙NO from nitrite ester (ONO-FA) was facilitated by ˙NO2. Furthermore, the release of ˙NO from NO2-cLA is the most favorable in the nitrite ester mechanism. In an aqueous environment, the modified Nef reaction was shown to be feasible. In addition, the release of ˙NO from 10- and 12-NO2-LA involves a larger reaction barrier and is more endergonic than those from 9- and 13-NO2-LA.
AB - Nitrated fatty acids (NO2-FAs) exhibit a variety of important biological attributes, including a nitric oxide (˙NO) donor and a cell-signaling molecule. We investigated the mechanisms of fatty-acid nitration, and the release of ˙NO from NO2-FAs. NO2-FAs are formed effectively by the addition of ˙NO2, followed by either hydrogen abstraction or addition of a second NO2. The latter reaction results in a vicinal nitronitrite ester form of FA, which isomerizes into vicinal nitrohydroxy FA via hydronium ion catalysis. The nitrohydroxy FAs exist in equilibria with NO2-FAs. Nitration of conjugated linoleic acid (cLA) was proved to be significantly more efficient than that of LA. In a nonaqueous environment, release of ˙NO from nitrite ester (ONO-FA) was facilitated by ˙NO2. Furthermore, the release of ˙NO from NO2-cLA is the most favorable in the nitrite ester mechanism. In an aqueous environment, the modified Nef reaction was shown to be feasible. In addition, the release of ˙NO from 10- and 12-NO2-LA involves a larger reaction barrier and is more endergonic than those from 9- and 13-NO2-LA.
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U2 - 10.1002/jccs.201800136
DO - 10.1002/jccs.201800136
M3 - Article
AN - SCOPUS:85054490151
VL - 66
SP - 41
EP - 48
JO - Journal of the Chinese Chemical Society
JF - Journal of the Chinese Chemical Society
SN - 0009-4536
IS - 1
ER -