ISSN:
1573-3904
Keywords:
β-amino acid
;
β-sheet
;
β-turn
;
cis-β-amino-cyclopropane carboxylic acid
;
endo-2-amino-3-carboxy-norborn-5-ene
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The desymmetrisation of endo-norborn-5-ene-2,3-dicarboxylic anhydride by proline esters has been used to prepare conformationally constrained pseudo-peptides with two peptide chains parallel to one another. A Curtius rearrangement on the desymmetrisation adduct produced the corresponding isocyanate which was used to prepare both a peptide incorporating an endo-2-amino-3-carboxy-norborn-5-ene unit, and a pseudo-peptide with two peptide chains parallel to one another but offset by the presence of a urea unit. The conformational analysis of the resulting peptides was carried out, and the norbornene unit was found to induce the formation of β-turns and parallel β-sheets.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1008870919209
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