1996 Bader Award Lecture Aminoacyl ethyl phosphates. Biomimetically activated amino acids

Aminoacyl ethyl phosphates are functional analogues of aminoacyl adenylates, the activated intermediates formed by ribosomal enzymes from the reaction of amino acids with ATP. The aminoacyl ethyl phosphates are prepared by DCC-mediated coupling of a tetraalkylammonium salt of ethyl phosphate and an...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 74; no. 12; pp. 2395 - 2400
Main Authors Kluger, Ronald, Li, Xianfeng, Loo, Richard W
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.12.1996
CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
aminoacyl phosphates
acyl phosphates
amino acids
biomimetic aminoacylation
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Summary:Aminoacyl ethyl phosphates are functional analogues of aminoacyl adenylates, the activated intermediates formed by ribosomal enzymes from the reaction of amino acids with ATP. The aminoacyl ethyl phosphates are prepared by DCC-mediated coupling of a tetraalkylammonium salt of ethyl phosphate and an N-t-Boc-amino acid, followed by deprotection. The efficiency of the synthesis and the solubility properties of the product depend on the alkyl group in the ammonium counterion of the phosphate. N-Protected and free aminoacyl ethyl phosphates hydrolyze slowly ( in neutral solution, 25 °C, ~100 h). These materials are potentially useful in biomimetic peptide synthesis, protein modification, and aminoacylation of RNA. Key words: amino acids, acyl phosphates, aminoacyl phosphates, biomimetic aminoacylation.
ISSN:0008-4042
1480-3291
DOI:10.1139/v96-268