Asymmetric synthesis of 3-substituted proline chimeras bearing polar side chains of proteinogenic amino acids.
The amino-zinc-ene-enolate cyclization reaction is a straightforward route to the synthesis of 3-substituted prolines. Herein we report the application of this reaction to the syntheses of proline chimeras of lysine, glutamic acid, glutamine, arginine, and serine. All these compounds were obtained in enantiomerically pure form and suitably protected for peptide synthesis.
Quancard
Jean
J
Synthèse, Structure et Fonction de Molécules Bioactives, CNRS/UMR 7613, Université Pierre et Marie Curie, 4 Place Jussieu, 75252 Paris Cedex 05, France.
Labonne
Aurélie
A
Jacquot
Yves
Y
Chassaing
Gérard
G
Lavielle
Solange
S
Karoyan
Philippe
P
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000596:Amino Acids; D011392:Proline; D015032:Zinc