Chemical Studies on Nucleic Acid Analogues

Dicarbonyl aldehydes are known to react preferentially with guanine residues in both DNA and RNA; however, the exact structure of the modification product has never been assigned unequivocally as either the "linear" or the "bent" isomer. Accordingly, we have synthesized the products of guanine modification with both glyoxal (an (alpha)-dialdehyde) and methylmalondialdehyde (a (beta)-dialdehyde) from a common precursor in four and eight steps, respectively, using a sequence which allows us to distinguish between the two potential structural isomers. For each product, open-ring precursors were prepared which could be differentiated unambiguously from their isomeric counterparts by NMR, owing to the magnetic equivalence of the imidazole or pyrimidine protons. Ring-closure of each precursor affords in one or two steps the corresponding guanine modification products which can for the first time be assigned unequivocally as the "linear" isomers.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

1981

Author dc:creator

• Czarnik, Anthony William, Jr.

• Chemistry, Organic

Language dc:language

eng

Identifier

(UMI)AAI8203438

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/67289