Synthesis of Glycidol- and Sugar-Derived Bicyclic β- and γ/δ-Amino Acids for Peptidomimetic Design

Constrained bicyclic β‐ and γ/δ‐amino acids using glycidol and sugar derivatives were developed. The synthetic strategies involved epoxide ring opening of a glycidol derivative, and subsequent coupling with sugar‐derived amines, leading to di‐ or trisubstitued bicyclic scaffolds after cyclisation wi...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2005-10, Vol.2005 (20), p.4372-4381
Main Authors: Danieli, Elisa, Trabocchi, Andrea, Menchi, Gloria, Guarna, Antonio
Format: Article
Language:English
Subjects:
Amino acids
Peptides
Peptidomimetics
Ring opening
Scaffold
Solid-phase synthesis
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Summary:Constrained bicyclic β‐ and γ/δ‐amino acids using glycidol and sugar derivatives were developed. The synthetic strategies involved epoxide ring opening of a glycidol derivative, and subsequent coupling with sugar‐derived amines, leading to di‐ or trisubstitued bicyclic scaffolds after cyclisation with trifluoroacetic acid. Achievement of β‐ or γ/δ‐amino acids was accomplished by changing the protecting group strategy of the starting materials. Compatibility of the scaffold with solid‐phase peptide synthesis was assessed by preparing model peptidomimetics using acid‐ and base‐labile resins, thus giving a new tool for peptidomimetic design. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500386