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

Gengjie Lin | Zendy; Yajun Jian | Zendy; Hao OuYang | Zendy; Lei Li | Zendy

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

Author(s) -

Gengjie Lin,

Yajun Jian,

Hao OuYang,

Lei Li

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502433h

Subject(s) - chemistry , deamination , adduct , pyrimidine , pyrimidine dimer , thymine , photochemistry , hydrolysis , molecule , cyclobutane , ring (chemistry) , dna , medicinal chemistry , stereochemistry , organic chemistry , dna damage , enzyme , biochemistry

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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