Synthesis of peptides with alpha,beta-dehydroamino acids. XIII photoisomerization of Ac-(Z)-delta Phe-NHMe: Ac-(E)-delta Phe-NHMe.
Easily accessible Ac-(Z)-delta Phe-NHMe was photoisomerized to so far unknown Ac-(E)-delta Phe-NHMe. Some parameters of the process leading to a diastereomeric mixture of ratio 90(Z):10(E) have been tested and the photoisomerization has been carried out on a preparative milligram scale. The isomers were separated via crystallization followed by preparative HPLC.
Kubica
Z
Z
Department of Organic Chemistry, University of Opole, Poland.
Koźlecki
T
T
Rzeszotarska
B
B
D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides / Q000138:chemical synthesis*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D010777:Photochemistry; D013237:Stereoisomerism
D010455:Peptides; C406472:acetyl-alpha,beta-dehydrophenylalanine methylamide; D010649:Phenylalanine