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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2014
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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. |
format | Online Article Text |
id | pubmed-4184442 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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