Abstract:
:Delta-amino acids are very attractive in drug discovery, especially in the peptidomimetic area, because of their capability to act as dipeptide isosteres and reverse turn mimetics. Herein we report the synthesis of a rigid delta-amino acid constrained by a 3-aza-6,8-dioxabicyclo[3.2.1]octane-based scaffold, which can be considered as a Gly-Asn dipeptide mimetic. Key steps are the condensation of glycidol and tartaric acid derivatives, and the intramolecular trans-acetalization of the oxidized adduct to give the bicyclic delta-amino acid. Starting from L-tartaric acid derivative, it was achieved the corresponding Gly-D-Asn isostere, whereas from the enantiomeric D-tartaric acid derivative the corresponding Gly-L-Asn isostere could be obtained, thus giving access to both enantiomeric dipeptide sequences.
journal_name
Amino Acidsjournal_title
Amino acidsauthors
Trabocchi A,Menchi G,Danieli E,Guarna Adoi
10.1007/s00726-007-0636-7subject
Has Abstractpub_date
2008-06-01 00:00:00pages
37-44issue
1eissn
0939-4451issn
1438-2199journal_volume
35pub_type
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