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|a 10.1021/acs.langmuir.1c03173
|2 doi
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|a pubmed25n1118.xml
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|a eng
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|a Zhang, Lei
|e verfasserin
|4 aut
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|a Surface-Induced Keto-Enol Tautomerization of DNA Base Molecules and Consequent [4 + 2]-like Cycloaddition on Si(111)7×7
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|c 2022
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
|b c
|2 rdamedia
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|a ƒa Online-Ressource
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|2 rdacarrier
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|a Date Completed 01.02.2022
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|a Date Revised 01.02.2022
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a Adsorption and film growth of deoxyribonucleic acid (DNA) base molecules (cytosine, guanine, thymine, and adenine) on Si(111)7×7 have been studied by combining X-ray photoelectron spectroscopy (XPS) with ab initio calculations based on the density functional theory (DFT). Multiple tautomeric forms and keto-enol tautomerization are revealed by the O 1s, N 1s, and C 1s XPS spectra of the O-containing DNA bases: cytosine, guanine, and thymine. While the carbonyl group-containing keto tautomer is more stable in a thick film and in powder, the hydroxyl group-containing enol tautomer is found at the interface. The keto-enol tautomerization, as induced by the reactive Si(111)7×7 surface, leads to the formation of a conjugated aromatic six-membered ring with a delocalized π electron system and to the consequent [4 + 2]-like cycloaddition between the enol tautomer and the 7×7 surface. The DFT calculation suggests that the enol tautomer exhibits a kinetic advantage over the keto one for the [4 + 2]-like cycloaddition. Among the several plausible pathways for the cycloaddition provided by the enol tautomer, the experimentally determined one involves a ring N and ring C atom (a polar pair), rather than two ring C atoms (a nonpolar pair), to better match the polar Si adatom-restatom pair of the 7×7 surface. Furthermore, the reacted ring C atom does not have any attached terminal functional group (e.g., -NH2 and -OH). Further deposition leads to continuous film growth in the keto tautomeric form for cytosine and guanine. For the only O-free DNA base molecule, adenine, dative bonding N → Si, rather than the [4 + 2]-like cycloaddition, is observed on the 7×7 surface. Of the four DNA base molecules, adenine is also the only one with its aromaticity maintained when adsorbed on the Si(111)7×7 surface. A reactive surface like the 7×7 surface could therefore provide a new control to trigger tautomerization that is often associated with genetic mutation
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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a Guanine
|2 NLM
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|a 5Z93L87A1R
|2 NLM
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|a Cytosine
|2 NLM
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|a 8J337D1HZY
|2 NLM
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|a DNA
|2 NLM
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|a 9007-49-2
|2 NLM
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|a Thymine
|2 NLM
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|a QR26YLT7LT
|2 NLM
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1 |
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|a Farkhondeh, Hanieh
|e verfasserin
|4 aut
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|a Rahsepar, Fatemeh Rahnemaye
|e verfasserin
|4 aut
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|a Chatterjee, Avisek
|e verfasserin
|4 aut
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|a Leung, Kam Tong
|e verfasserin
|4 aut
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| 773 |
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|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1985
|g 38(2022), 3 vom: 25. Jan., Seite 1266-1276
|w (DE-627)NLM098181009
|x 1520-5827
|7 nnas
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| 773 |
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|g volume:38
|g year:2022
|g number:3
|g day:25
|g month:01
|g pages:1266-1276
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|u http://dx.doi.org/10.1021/acs.langmuir.1c03173
|3 Volltext
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