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Rationale for this Dissertation
Design and Biological Activity of RetroInverso Enkephalins
3 other sections not shown
5M NaCl AcOH acyclic alkaloid alkaloid opiates amide bond amino acid anisole CHCl3/MeOH/AcOH Chem combined EtOAc washings compound conformational cooled solution 0°C cyclic analogs D-Ala desired product diastereomers dicyclohexylcarbodiimide dipeptide dipeptide salt diphenylphosphoryl azide enantiomer enzymatic degradation ester gem-diaminoalkyl guinea pig ileum high vacuum hour at 0°C HPLC hydrogen bonded ileum isomer isopropyl l0 ml Leu-enkephalin MeOH mmol Modified Enkephalin Analogs morphine mouse vas deferens N-hydroxysuccinimide N,N'-dicyclohexylurea OBzl opiate OSu H overnight at room partial retro-inverso pentapeptide peptide bond pig ileum assay potency protected pentapeptide R,S-2-isobutylmalonic acid reaction mixture receptor recrystallized reduced pressure removed under reduced residue triturated retro-inverso enkephalins retro-inverso modification Reverse phase HPLC reverse-phase HPLC Ring closure side chain solvent solvent removed solvent was removed stirring continued overnight structure Synthesis TLC Rf trifluoroacetate salt trifluoroacetic acid triturated Usual workup workup with EtOAc y-receptor yield the desired