Synthesis of a new azetidinyl γ-lactam based peptides 1-3 with the preference for β-turn conformation is discussed. The tripeptide model compounds, namely the trans and the corresponding cis isomers, were studied by H NMR spectroscopy to measure the temperature coefficients of the two NH photons. It was observed that temperature coefficient NH of glycine was lowest, phenyl alanine-NH has higher temperature coefficient, and for both the cis tripeptides the temperature coefficients of shifts for all the NHs are above 5.0. The results show that the stereochemistry of β-lactam ring plays a key role in controlling the conformation of the peptides.
A novel azetidinyl gamma-lactam based peptide with a preference for beta-turn conformation
BERTOLASI, Valerio
2005
Abstract
Synthesis of a new azetidinyl γ-lactam based peptides 1-3 with the preference for β-turn conformation is discussed. The tripeptide model compounds, namely the trans and the corresponding cis isomers, were studied by H NMR spectroscopy to measure the temperature coefficients of the two NH photons. It was observed that temperature coefficient NH of glycine was lowest, phenyl alanine-NH has higher temperature coefficient, and for both the cis tripeptides the temperature coefficients of shifts for all the NHs are above 5.0. The results show that the stereochemistry of β-lactam ring plays a key role in controlling the conformation of the peptides.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
