Acetylated glucopyranosyl esters of enkephalins.
Acetylated D-glucopyranosyl esters of enkephalins were prepared by two different fragment condensation procedures involving direct participation of imidazole in the ester linkage formation. By both methods anomeric mixtures of D-glucosyl esters were obtained and resolved by column chromatography. Depending on coupling conditions, racemization of either the C-terminal or the penultimate amino acid residue of the enkephalin molecule occurred. The glucoconjugates with inverted stereochemistry were quantitated and separated from the main product by reversed-phase high-performance liquid chromatography. The opioid agonist potencies of the synthesized glucopyranosyl esters of enkephalins on electrically stimulated guinea pig ileum and mouse vas deferens preparations were determined in comparison with [Leu5]enkephalin.
Skurić
M
M
Ruder Bosković Institute, Zagreb, Croatia.
Horvat
J
J
Horvat
S
S
Chung
N N
NN
Schiller
P W
PW
D000107:Acetylation; D000595:Amino Acid Sequence; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004558:Electric Stimulation; D004743:Enkephalin, Leucine / Q000494:pharmacology; D004745:Enkephalins / Q000737:chemistry* / Q000494:pharmacology; D004952:Esters / Q000737:chemistry; D006001:Glycoconjugates / Q000737:chemistry*; D006031:Glycosylation; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects / Q000502:physiology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D014649:Vas Deferens / Q000187:drug effects / Q000502:physiology
D004745:Enkephalins; D004952:Esters; D006001:Glycoconjugates; D004743:Enkephalin, Leucine