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Nucleic Acids Research, 1990, Vol. 18, No. 20 5989-5993
© 1990

CHEMISTRY

Identification and structural characterization of O-ß-ribosyl-(1''->2')-adenosine-5''-phosphate in yeast methionine initiator tRNA

Gérard Keith, Anne-Lise Glasser1, Jean Desgrés1, Kenneth C. Kuo2 and Charles W. Gehrke2

Institut de Biologie Moléculaire et Cellulaire du CNRS et de I'Université Louis Pasteur 67084 Strasbourg 1Laboratoire de Biochimie Médicale, Université de Bourgogne 21034 Dijon, France 2Department of Biochemistry, University of Missouri and Cancer Research Center Columbia, MO 65211, USA

Received July 17, 1990. Revised September 9, 1990. Accepted September 9, 1990.

We report in this paper on the complete structure determination of the modified nucleotlde A*, now called Ar(p), that was previously identified in yeast methionine initiator tRNA as an isomeric form of O-ribosyl-adenoslne bearing an additional phosphoryl-monoester group on its ribose2 moiety. By using the chemical procedure of periodate oxidation and subsequent ß-elimlnation with cyclohexylamine on mono- and dinucleotides containing Ar(p), we characterized the location of the phosphate group on the C-5'' of the ribose2 moiety, and the linkage between the two riboses as a (1''->2')-glycosidic bond. Since the structural difference between phosphatase treated Ar(p) and authentic O-{alpha}-ribosyl-(1''->2')-adenoslne from poly(ADP-Ribose) was previously assigned to an isomeric difference in the ribose2-ribose1 linkage, the (1''2')-glycosidic bond of Ar(p) was deduced to have a ß-spatial configuration. Thus, final chemical structure for Ar(p) at the position 64 in yeast initiator tRNAMet has been established as O-ß-ribosyl-(1''->2')adenosine-5''-phosphate. This nucleotide is linked by a 3',5'-phosphodiester bond to G at the position 65.


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