Synthesis of a novel conformationally restricted Val-Phe dipeptidomimetic.
A method for the synthesis of (3(R,S),6S,11b(R,S))-1,3,4,6,7,11b-hexahydro-4-oxo-3-phthalimidopyrido[2,1-a]isoquinoline-6-carboxylic acid 2 as a new conformationally restricted dipeptidomimetic of Val-Phe is reported. It involved cyclisation via an intramolecular electrophilic addition at the reactive bridgehead carbon. This new scaffold can be used as a building block in the preparation of libraries of peptidomimetics.
Gilleron
Pauline
P
Institut de Chimie Pharmaceutique Albert Lespagnol, EA 2692, Université de Lille 2, BP 83, 59006 Lille, France.
Millet
Régis
R
Domarkas
Juozas
J
Farce
Amaury
A
Houssin
Raymond
R
Hénichart
Jean-Pierre
JP
D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D018716:Molecular Mimicry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010649:Phenylalanine / Q000737:chemistry*; D011487:Protein Conformation; D014633:Valine / Q000737:chemistry*
D004151:Dipeptides; D010649:Phenylalanine; D014633:Valine