Hans Jeschkeit

Synthetische und NMR-spektroskopische Untersuchungen der Benzylaminaddition an N-Maleyl-aminosäurederivate

SummaryDuring the addition of amines to maleylamino acids in general β-amino derivatives are formed. In order to change the reactivity within the vinylogous maleyl system we introduced the β-benzylester group into the starting compound N-(cis-β-carboxyacryloyl)-phenylalanine methylester1. The obtained benzylester2 is adding benzylamine in α-position yielding N-benzyl-α-aspartyl(β-benzyl)-phenylalanine methylester4. The addition reaction was investigated by1H-NMR-spectroscopy. The structures of the compounds have been confirmed by elemental analysis, IR,1H-NMR and13C-NMR spectroscopy.

Effects of differing chirality on the hydrogen-bonding behaviour of di- and tri-peptide derivatives

The self-association of di- and tri-peptide derivatives with a well-defined configuration at their chiral C atoms and 1 : 1 mixed diastereoisomeric pairs of these tripeptide derivatives have been investigated by means of IR spectroscopy in CH2Cl2. In most–but not in all–cases major differences in the association behaviour have been recorded on changing the configuration at only one C atom.