Stereoselective formation of a 2′(3′)-aminoacyl ester of a nucleotide |
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Authors: | Arthur L Weber |
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Institution: | (1) The Salk Institute for Biological Studies, P.O. Box 85800, 92138 San Diego, California, USA |
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Abstract: | Summary Reaction ofDl-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 ofd-serine incorporated into 2(3)-O-seryl-adenosine-5-(O-methylphosphate) was about 9%. Adenylyl-(5N)-serine and an unknown product also incorporated an excess ofd-serine; however, serylserine showed an excess ofl-serine. The relationship of these results to the origin of the biological pairing ofl-amino acids and nucleotides containingd-ribose is discussed. |
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Keywords: | Stereoselection Amino acid activation Aminoacyl nucleotide ester Prebiotic chemistry Origin of optical activity Nucleotide Molecular evolution |
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