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Synthesis of Glycidol‐ and Sugar‐Derived Bicyclic β‐ and γ/δ‐Amino Acids for Peptidomimetic Design
Author(s) -
Danieli Elisa,
Trabocchi Andrea,
Menchi Gloria,
Guarna Antonio
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500386
Subject(s) - peptidomimetic , chemistry , glycidol , bicyclic molecule , trifluoroacetic acid , amino acid , trifluoroacetic anhydride , epoxide , combinatorial chemistry , organic chemistry , stereochemistry , peptide , catalysis , biochemistry
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)