Jan 1, 1987

Stereoselective formation of a 2'(3')-aminoacyl ester of a nucleotide

Journal of Molecular Evolution
A L Weber


Reaction of DL-serine and adenosine-5-phosphorimidazolide in the presence of adenosine-5'-(O-methylphosphate) and imidazole resulted in the stereoselective synthesis of the aminoacyl nucleotide ester 2'(3')-O-seryl-adenosine-5'-(O-methylphosphate). The enantiomeric excess of D-serine incorporated into 2'(3')-O-seryl-adenosine-5'-(O-methylphosphate) was about 9%. Adenylyl-(5'----N)-serine and an unknown product also incorporated an excess of D-serine; however, serylserine showed an excess of L-serine. The relationship of these results to the origin of the biological pairing of L-amino acids and nucleotides containing D-ribose is discussed.

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Mentioned in this Paper

Molecular Stereochemistry
adenosine 5'-phosphoroimidazolide
Amino Acids, I.V. solution additive
aminoacyl nucleotide
5'-Adenylic Acid

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