Abstract:
:In a previous paper, 2'-deoxy-N(6)-methoxyadenosine (mo(6)A) was shown to form a mismatch base-pair with 2'-deoxycytidine with a Watson-Crick-type geometry. To fully understand the structural basis of genetic mutations with damaged DNA, it is necessary to examine whether the methoxylated adenine residue still has the ability to form the regular Watson-Crick pairing with a thymine residue. Therefore, a DNA dodecamer with the sequence d(CGCGmo(6)AATTCGCG) has been synthesized and its crystal structure determined. The methoxylation has no significant effect on the overall DNA conformation, which is that of a standard B-form duplex. The methoxylated adenine moieties adopt the amino tautomer with an anti conformation around the C(6)-N(6) bond to the N(1) atom, and they form a Watson-Crick base-pair with thymine residues on the opposite strand, similar to an unmodified adenine residue. It is concluded that methoxylated adenine can present two alternate faces for base-pairing, thanks to the amino<-->imino tautomerism allowed by methoxylation. Based on this property, two gene transition routes are proposed.
journal_name
J Mol Bioljournal_title
Journal of molecular biologyauthors
Chatake T,Hikima T,Ono A,Ueno Y,Matsuda A,Takénaka Adoi
10.1006/jmbi.1999.3304keywords:
subject
Has Abstractpub_date
1999-12-17 00:00:00pages
1223-30issue
5eissn
0022-2836issn
1089-8638pii
S0022-2836(99)93304-1journal_volume
294pub_type
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