ISSN:
0170-2041
Keywords:
Catalysis
;
Guanidine
;
Ion pair
;
Phosphoric acid diester
;
Staphylococcal nuclease, model of
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Acceleration of Substitution Reactions of a Phosphoric Acid Diester by Bis(guanidinium) CompoundsIon-pair coordination of phosphoric acid diesters with positively charged guanidines may cause large rate accelerations in substitution reactions. Here we present a comparative study on the catalytical influence of several mono- bis- and tris(guanidines) and of other cationic compounds. Large rate effects occur if 1,3-bis(aminomethyl)benzene or 1,2-ethylenediamine are used as spacers. Further acceleration can be achieved by exchanging guanidinium groups by 2-aminoimidazolines. The 4800-fold rate enhancement seen in the best case demonstrates the importance of the bis(guanidinium) moiety of staphylococcal nuclease and gives good perspectives towards future uses of guanidinium compounds as RNA cleaving agents.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940110
