Folding propensity of cyclohexylether-delta-peptides |
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Authors: | Arndt Hans-Dieter Ziemer Burkhard Koert Ulrich |
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Institution: | Humboldt-Universit?t zu Berlin, Institut für Chemie, Brook-Taylor-Str. 2, D-12489 Berlin, Germany. |
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Abstract: | structure: see text] Linear (n = 2-18) and cyclic oligomers (n = 3-8) of a cyclohexylether-delta-amino acid (COA) were prepared in high yield and stereopurity. CD spectra of the linear oligomers were indicative of secondary structure formation. X-ray crystal structures of cyclic COA oligomers revealed hydrophobic packing and internal 5- and 10-membered-ring hydrogen bonds. Ether and amide oxygens reside preferably in an ap orientation. This conformational locking is apparently broken by a C-2 substituent in an asymmetric cyclotrimer, for which a zeolithe-like tubular structure was found. |
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