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Volumn 72, Issue 17, 2007, Pages 6548-6555

Acidity and proton affinity of hypoxanthine in the gas phase versus in solution: Intrinsic reactivity and biological implications

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLADENINE DNA GLYCOSYLASE (AAG); GLYCOSYLASE ENZYMES; HYPOXANTHINE;

EID: 34547947830     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070996x     Document Type: Article
Times cited : (49)

References (95)
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    • In E. coli, 3-methyladenine DNA glycosylase II (AlkA) excises hypoxanthine. For reviews, see refs 29 and 30.
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    • When alkylated, adenosine and guanosine form positively charged substrates (3-methyladenosine and 7-methylguanosine); these may bind to the AAG active site as charged substrates. This paper focuses on AAG substrates such as hypoxanthine and ethenoadenine, which are believed to bind as neutrals. See refs 28-32.
    • When alkylated, adenosine and guanosine form positively charged substrates (3-methyladenosine and 7-methylguanosine); these may bind to the AAG active site as charged substrates. This paper focuses on AAG substrates such as hypoxanthine and ethenoadenine, which are believed to bind as neutrals. See refs 28-32.
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    • N1. Furthermore, the mechanism for enzyme cleavage also involves a "base-flipping" step, whereby the nucleobase is "flipped" into the enzyme active site; this step may also differ for different substrates. It is not known whether base flipping is a relatively fast or slow step in AAG, and herein we focus on the steps involving actual nucleobase excision. See refs 28-30.
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    • The ΔΔS value obtained for hypoxanthine from our Cooks extended kinetic method experiments is 5 cal K-1 mol-1. It has been noted that the ΔΔS value is related to the accuracy of the PA value obtained by the Cooks extended method. Ideally, the actual ΔΔS value should be less than or equal to about 5 cal K-1 mol-1; otherwise, the extended kinetic method may underestimate the PA. Another caveat is that the ΔΔS value obtained from the extended method is often itself underestimated. There is therefore a possibility that the PA value of 222 kcal mol-1 obtained via our Cooks extended method experiment is too low; however, given that the bracketing result gives a PA of 217.5-220.2 kcal mol-1, we are inclined to believe that the extended kinetic method value is not highly underestimated
    • -1, we are inclined to believe that the extended kinetic method value is not highly underestimated.
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    • -1. We are not sure why their results differ slightly from ours, but the difference is very small and does not change the conclusions herein.
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    • Gas-phase calculations indicate that the most basic site of hypoxanthine and guanine is N7; for adenine it is N1. The general acid catalyst for AAG has not been identified so it is as yet unknown whether an acid is proximal enough to both the N7 of hypoxanthine and guanine as well as to the N1 of adenine to effect protonation. See refs 28 and 32.
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