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β-Turns in bridged proline-containing cyclic peptide models

✍ Scribed by M. Hollósi; K. E. Kövér; S. Holly; L. Radics; G. D. Fasman

Publisher
Wiley (John Wiley & Sons)
Year
1987
Tongue
English
Weight
967 KB
Volume
26
Category
Article
ISSN
0006-3525

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✦ Synopsis

The syntheais, CD, ir spectroscopic, and conformational studies of a series of bridged cyclic peptides of the general formula, q&[NH-(CH,),-CO-Gly-Pro-Y-Gly] (2a-d, Y = Gly or Ser(OBu'), n = 4 or 2) is reported. As indicated by difference nuclear Overhauser enhancement and Fourier transform ir experiments, the tetrapeptide sequence of qch[NH-(CH,),-CO-Gly-Pro-Gly-Gly] (2a) and q&[NH-(CH,),-CO-Gly-F'ro-Gly-Gly] (2b) adopts a 1 + 4 hydrogenbonded type I1 8-turn conformation in solution, while qch[NH-(CH2),-CO-Gly-Pro-Ser(OBut)-Gly] (2c) features a type I 8-turn, fixed by 1 + 4 and 07.. . NH intramolecular H bonds. In aqueous solution 2a and 2c show class B and class C CD spectra, respectively. This is the first case reported of a typical claas C CD pattern in aqueous solution for a conformationally mobile system having a type I 8-turn. Based on the comparison of the band intensities of the bridged models with those of linear and cyclic model systems reported earlier, a set of subspectra with reduced band intensities is suggested for use in the CD analysis of the conformation of polypeptides in solution.

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