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Stereoselective aminoacylation of a dinucleoside monophosphate by the imidazolides of DL-alanine and N-(tert-butoxycarbonyl)-DL-alanineThe aminoacylation of diinosine monophosphate was studied experimentally. When the acylating agent was the imidazolide of N-(tert-butoxycarbonyl)-DL-alanine, a 40 percent enantiomeric excess of the isomer was incorporated at the 2' site and the positions of equilibrium for the reversible 2'-3' migration reaction differed for the D and L enantiomers. The reactivity of the nucleoside hydroxyl groups was found to decrease on the order 2'(3') less than internal 2' and less than 5', and the extent of the reaction was affected by the concentration of the imidazole buffer. Reaction of IpI with imidazolide of unprotected DL-alanine, by contrast, led to an excess of the D isomer at the internal 2' site. Finally, reaction with the N-carboxy anhydride of DL-alanine occurred without stereoselection. These results are found to be relevant to the study of the evolution of optical chemical activity and the origin of genetically directed protein synthesis.
Document ID
19840059712
Document Type
Reprint (Version printed in journal)
Authors
Profy, A. T. (Cornell Univ. Ithaca, NY, United States)
Usher, D. A. (Cornell University Ithaca, NY, United States)
Date Acquired
August 12, 2013
Publication Date
January 1, 1984
Publication Information
Publication: Journal of Molecular Evolution
Volume: 20
Issue: 2 19
ISSN: 0022-2844
Subject Category
SPACE BIOLOGY
Funding Number(s)
CONTRACT_GRANT: NIH-GM-26249
CONTRACT_GRANT: NAGW-493
CONTRACT_GRANT: NIH-GM-07273
Distribution Limits
Public
Copyright
Other