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Acid‐catalysed depurination of DI‐, TRI‐ and polydeoxyribonucleotides: Effect of molecular environment on the cleavage of adenine residue
Author(s) -
Hakala Harri,
Oivanen Mikko,
Saloniemi Eija,
Gouzaev Andrei,
Lönnberg Harri
Publication year - 1992
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610051208
Subject(s) - chemistry , depurination , residue (chemistry) , cleavage (geology) , stereochemistry , organic chemistry , biochemistry , dna , geotechnical engineering , fracture (geology) , engineering
First‐order rate constants for the acid‐catalysed cleavage of adenine base from 2′‐deoxyadenosine, its 3′ ‐ and 5′‐ monophosphates, various dinucleoside monophosphates, trinucleoside diphosphates and hexameric 2′‐deoxyadenylic acid were measured by the method of initial velocity. The results obtained were compared with the effect that hetroassociation with caffeine has on the pre‐equilibrium protonation and rate‐limiting heterolysis of 2′ ‐deoxyadenosine and its isosteric analogue, 1‐(2‐deoxy‐β‐D‐ erythro ‐pentofuranosyl) benzimidazole. The kinetics of the depurination of poly (dA‐T), poly(dA) and a mixture of poly(dA) and poly(T) were determined, and the rate variations observed are discussed on the basis of the known structures of these polymers.