ISSN:
1573-1111
Keywords:
prolylproline derivatives
;
cation binding
;
carboxy ionophore model
;
, MM calculations
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The synthesis of N-(2-hydroxy-1-phenoxyacetyl)prolylproline 2 from 2-acetoxyphen-oxyacetic acid is described. A firstsynthesis led toN-(2-acetoxy-1-phenoxyacetyl)prolylproline methylester 8b that fragmented upon attempted esterhydrolysis with 1N NaOH. A second synthesis gave thecorresponding benzyl ester 13, which wasconverted to 2 by deacylation of the phenolicacetoxy group with pyrrolidine followed byhydrogenolysis of the ester. Cation binding by 2 in methanol and related molecular mechanics (MM)geometric optimizations are discussed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1008189330661
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