Tetrahedron p. 8505 - 8514 (1992)
Update date:2022-08-30
Topics:
Barawkar, Dinesh A.
Kumar, R. Krishna
Ganesh, K. N.
Substituents at 5-position of a pyrimidine base are known to affect its base pairing properties with complementary purines, either by altering the imino N3-H acidity or by modifying the acceptor strength of C2 and C4 carbonyls.This paper reports comparative base pair property of 5-methyl-2'-deoxyuridine (dT) and 5-amino-2'-deoxyuridine (dUNH2) with 2'-deoxyadenosine (dA) as their 3',5'-di-t-butyldimethylsilyl derivatives in chloroform-d.Using 1H and 13C NMR, it is demonstrated that the 5-NH2 substituent in 2'-deoxyuridine results in (i) decreased association (lower Ka) with 2'-deoxyadenosine compared to dA:dT complexation and (ii) increased receptor strength of C2 carbonyl compared to C4 carbonyl and (iii) lower temperature for separation of 6-amino protons of dA due to its complexation with dUNH2 compared to that with dT.
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