Mechanism of 1,N2-Etheno-2′-deoxyguanosine Formation from Epoxyaldehydes | Zendy

Katya Petrova | Zendy; Ravikumar S. Jalluri | Zendy; Ivan D. Kozekov | Zendy; Carmelo J. Rizzo | Zendy

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Mechanism of 1,N²-Etheno-2′-deoxyguanosine Formation from Epoxyaldehydes

Author(s) -

Katya Petrova,

Ravikumar S. Jalluri,

Ivan D. Kozekov,

Carmelo J. Rizzo

Publication year - 2007

Publication title -

chemical research in toxicology

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.031

H-Index - 156

eISSN - 1520-5010

pISSN - 0893-228X

DOI - 10.1021/tx7001433

Subject(s) - chemistry , adduct , stereochemistry , deoxyguanosine , lipid peroxidation , reaction mechanism , aldehyde , schiff base , double bond , dna , biochemistry , organic chemistry , antioxidant , catalysis

Background levels of etheno adducts have been attributed to the reaction of DNA with 2,3-epoxyaldehydes, a proposed product of lipid peroxidation. We have examined the reaction of (2R,3S)-epoxyhexanal with dGuo to give 7-(1S-hydroxybutyl)-1,N(2)-etheno-dGuo. We observed that the stereochemistry of the side chain scrambled over time. This process provided insight into the mechanism for the formation of 1,N(2)-etheno-dGuo from 4,5-epoxy-2-decenal [Lee, S. H., et al.(2002) Chem. Res. Toxicol. 15, 300-304]. The mechanistic proposal predicts that 2-octenal is a by-product of the reaction. The reaction of 4,5-epoxy-2-decenal was reinvestigated, and the 2-octenal adduct of dGuo was identified as a product of this reaction in support of the mechanistic proposal. Also observed are products that appear to be derived from 2,3-epoxyoctanal, which can be formed through Schiff base formation of 4,5-epoxy-2-decenal with the dGuo followed by hydration of the double bond and retro-aldol reaction.

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