ISSN:
0170-2041
Keywords:
Hydrogen bonds
;
Ion pairs
;
Molecular recognition
;
Phosphoric acid diester
;
Staphylococcal nuclease, model of
;
Enzymes, models of
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Supramolecular Phosphorylation of Cationic Alcohols with a 3-Arylindole-4-carboxamidine FrameworkRecently we reported on the synthesis of 8-phenylnaphthalene-1-carboxamidines equipped with nucleophilic side chains (1, 2). In the protonated state these compounds were able to coordinate phosphoric acid diesters as ion-pair complexes and to react with them in a quasi-intramolecular way. In comparison with noncharged alcohols high-rate enhancements of phosphorylation could be achieved. Now we describe the synthesis of analogous amidinium alcohols constructed from a 3,4-disubstituted indole framework. Due to the five-membered ring of the indole the angle between the substituents of 4 and 5 is extended compared to the naphthalene derivatives 1 and 2. As a result from this structural change a slight increase of the phosphorylation rate of 4 is observed.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419941213
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