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Synthesis of an azabicycloalkane amino acid scaffold as potential rigid dipeptide mimetic

✍ Scribed by Régis Millet; Juozas Domarkas; Pauline Rombaux; Benoı̂t Rigo; Raymond Houssin; Jean-Pierre Hénichart

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
67 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Short syntheses are presented of the pseudo-dipeptide (3S,6S)-6-[(benzyloxy)carbonyl]amino-5-oxo-1,2,3,5,6,7-hexahydro-3-indolizinecarboxylic acid (1a) and of its (3S,6R) diastereoisomer (1b). The key step involves adding vinylogous b-enaminoester derived from pyroglutamic acid on an acrylate derivative. The 6,5-fused bicyclic lactam obtained may be viewed as a conformationally restricted Ala-Pro mimetic.

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Conformational Analysis of Azabicycloalk
Conformational Analysis of Azabicycloalkane Amino Acid Scaffolds as Reverse-Turn Inducer Dipeptide Mimics
✍ Laura Belvisi; Anna Bernardi; Leonardo Manzoni; Donatella Potenza; Carlo Scolast 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 312 KB 👁 2 views

In an effort to design structural mimics of protein and peptide reverse-turns, the conformations of 5,5-, 6,5-, and 7,5-fused 1-aza-2-oxobicycloalkane amino acids have been evaluated. The conformational preferences of these proline-derived bicyclic lactams have been studied by Monte Carlo molecular