ISSN:
1573-3904
Keywords:
Pseudopeptide
;
Turn mimic
;
Vinylogous peptides
;
X-ray diffraction
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract A Z- or E-ethenyl group has been inserted between the α-carbon andthe carboxyl group of the proline residue by stereoselective Hornersynthesis. The resulting vinylogous amino acid has been coupled with aminocompounds by classical methods, and model amino acid derivatives anddipeptides containing a Z- or E-CH=CMe group have been investigated insolution by 1H-NMR and IR spectroscopy, and in the solid stateby X-ray diffraction. The E-ethenyl group gives rise to an openconformation and the Z-conformer to a folded structure with anintramolecular hydrogen bond closing a nine-membered pseudocycle.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1008846232043
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