An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct

[Image: see text] Pyrimidine (6-4) pyrimidone photoproduct (6-4PP), a common DNA photolesion formed under solar irradiation, was indicated to hydrolyze under strong basic conditions, breaking the N3–C4 bond at the 5′-thymine. The reanalysis of this reaction revealed that the resulting water adduct m...

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Autores principales: Lin, Gengjie, Jian, Yajun, Ouyang, Hao, Li, Lei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184442/
https://www.ncbi.nlm.nih.gov/pubmed/25250878
http://dx.doi.org/10.1021/ol502433h
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author Lin, Gengjie
Jian, Yajun
Ouyang, Hao
Li, Lei
author_facet Lin, Gengjie
Jian, Yajun
Ouyang, Hao
Li, Lei
author_sort Lin, Gengjie
collection PubMed
description [Image: see text] Pyrimidine (6-4) pyrimidone photoproduct (6-4PP), a common DNA photolesion formed under solar irradiation, was indicated to hydrolyze under strong basic conditions, breaking the N3–C4 bond at the 5′-thymine. The reanalysis of this reaction revealed that the resulting water adduct may not be stable as previously proposed; it readily undergoes an esterification reaction induced by the 5-OH group at 6-4PP to form a five-membered ring, eliminating a molecule of ammonia.
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spelling pubmed-41844422015-09-24 An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct Lin, Gengjie Jian, Yajun Ouyang, Hao Li, Lei Org Lett [Image: see text] Pyrimidine (6-4) pyrimidone photoproduct (6-4PP), a common DNA photolesion formed under solar irradiation, was indicated to hydrolyze under strong basic conditions, breaking the N3–C4 bond at the 5′-thymine. The reanalysis of this reaction revealed that the resulting water adduct may not be stable as previously proposed; it readily undergoes an esterification reaction induced by the 5-OH group at 6-4PP to form a five-membered ring, eliminating a molecule of ammonia. American Chemical Society 2014-09-24 2014-10-03 /pmc/articles/PMC4184442/ /pubmed/25250878 http://dx.doi.org/10.1021/ol502433h Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Lin, Gengjie
Jian, Yajun
Ouyang, Hao
Li, Lei
An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct
title An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct
title_full An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct
title_fullStr An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct
title_full_unstemmed An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct
title_short An Unexpected Deamination Reaction after Hydrolysis of the Pyrimidine (6-4) Pyrimidone Photoproduct
title_sort unexpected deamination reaction after hydrolysis of the pyrimidine (6-4) pyrimidone photoproduct
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184442/
https://www.ncbi.nlm.nih.gov/pubmed/25250878
http://dx.doi.org/10.1021/ol502433h
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