The solid-phase synthesis and characterization of a series of peptides (4-15) containing reverse-turn mimetic bicyclic lactams is reported. The bicyclic lactams (1a, 1b) possess high structural similarity to the two central residues of a Pturn. Amino acid conjugates of these bicyclic lactams were synthesized on solid supports following a g-fluorenylmethoxycarbonyl (FMOC) protection strategy on WangMerrifield resin. Coupling between amino acids was accomplished by means of diisopropylcarbodiimide (DIC)/ hydroxyazabenzotriazole (HOAt). Coupling between amino acids and the mimics was performed with the potent Carpino's reagent O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramelhyluronium hexafluorophosphate (HATU). The final compounds were cleaved from the resin and obtained as N-acetylated methyl esters or benzyl amides.

Solid-phase synthesis of peptides containing reverse-turn mimetic bicyclic lactams / C.M.A. Gennari, A. Mielgo, D. Potenza, C. Scolastico, U. Piarulli, L. Manzoni. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 1999:2(1999), pp. 379-388. [10.1002/(SICI)1099-0690(199902)1999:2<379::AID-EJOC379>3.0.CO;2-B]

Solid-phase synthesis of peptides containing reverse-turn mimetic bicyclic lactams

C.M.A. Gennari
Primo
;
D. Potenza;C. Scolastico;
1999

Abstract

The solid-phase synthesis and characterization of a series of peptides (4-15) containing reverse-turn mimetic bicyclic lactams is reported. The bicyclic lactams (1a, 1b) possess high structural similarity to the two central residues of a Pturn. Amino acid conjugates of these bicyclic lactams were synthesized on solid supports following a g-fluorenylmethoxycarbonyl (FMOC) protection strategy on WangMerrifield resin. Coupling between amino acids was accomplished by means of diisopropylcarbodiimide (DIC)/ hydroxyazabenzotriazole (HOAt). Coupling between amino acids and the mimics was performed with the potent Carpino's reagent O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramelhyluronium hexafluorophosphate (HATU). The final compounds were cleaved from the resin and obtained as N-acetylated methyl esters or benzyl amides.
FMOC strategy; Peptidomimetics; Reverse-turns; Solid-phase synthesis
Settore CHIM/06 - Chimica Organica
http://onlinelibrary.wiley.com/doi/10.1002/(SICI)1099-0690(199902)1999:2%3C379::AID-EJOC379%3E3.0.CO;2-B/abstract
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/175563
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