Original scientific paper

4-Amino- and 4-Hydroxycyclohexane-1,1-dicarboxylic Acid Peptides

V. Škarić ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« I nstitute, 41001 Zagreb, Croatia, Yugoslavia
J. Makarević ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« I nstitute, 41001 Zagreb, Croatia, Yugoslavia

Abstract

4-Amino-, 4-oxo-, and 4-hydroxy-cyclohexane-1 ,1-dicarboxylic
acids have been inserted into di- and tri-peptides containing
glycine, L-phenylalanine, L-cyclohexylalanine, and L-tyrosine. The
geometries of 4-c-(IX A) and 4-t-(IX B) benzamidocyclohexane-
r-1-carboxy-1-carbonyl-L-phenylalanine methyl esters and 4-c-
-(XXIII A) and 4-t-(XXIII B) benzoxycyclohexane-r-1 -carbomethoxy-
1-carbonyl-L-cyclohexylalanine methyl esters were confirmed
by their NMR spectra and intramolecular cyclisations of
the cis isomers. The ring opening of 2-oxabicyclo[2.2.2]octan-3-one-
4-carbonyl-L-cyclohexylalanine methyl ester (XXIV) in methanolic
hydrochloric acid afforded 4-c-hydroxycyclohexane-r- 1-
-carbomethoxy-1-carbonyl-L-cyclohexylalanine methyl ester (XXI
A) which on benzoylation was converted into the product identical
with the isomer (XXIII A).

Keywords

Hrčak ID:

194324

URI

https://hrcak.srce.hr/194324

Publication date:

31.12.1981.

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