Solid-Phase Synthesis of Peptides Containing Reverse-Turn Mimetic Bicyclic Lactams
1999; Wiley; Volume: 1999; Issue: 2 Linguagem: Inglês
10.1002/(sici)1099-0690(199902)1999
ISSN1434-193X
AutoresCesare Gennari, Antonia Mielgo, Donatella Potenza, Carlo Scolastico, Umberto Piarulli, Leonardo Manzoni,
Tópico(s)Carbohydrate Chemistry and Synthesis
ResumoEuropean Journal of Organic ChemistryVolume 1999, Issue 2 p. 379-388 Full Paper Solid-Phase Synthesis of Peptides Containing Reverse-Turn Mimetic Bicyclic Lactams Cesare Gennari, Cesare Gennari [email protected] Search for more papers by this authorAntonia Mielgo, Antonia Mielgo Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this authorDonatella Potenza, Donatella Potenza Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this authorCarlo Scolastico, Carlo Scolastico Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this authorUmberto Piarulli, Umberto Piarulli Istituto di Scienze Mat. Fis. e Chimiche, Università dell′Insubria, via Lucini 3, I-22100 Como, ItalySearch for more papers by this authorLeonardo Manzoni, Leonardo Manzoni Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this author Cesare Gennari, Cesare Gennari [email protected] Search for more papers by this authorAntonia Mielgo, Antonia Mielgo Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this authorDonatella Potenza, Donatella Potenza Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this authorCarlo Scolastico, Carlo Scolastico Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this authorUmberto Piarulli, Umberto Piarulli Istituto di Scienze Mat. Fis. e Chimiche, Università dell′Insubria, via Lucini 3, I-22100 Como, ItalySearch for more papers by this authorLeonardo Manzoni, Leonardo Manzoni Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,Search for more papers by this author First published: 18 January 1999 https://doi.org/10.1002/(SICI)1099-0690(199902)1999:2 3.0.CO;2-BCitations: 17AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat 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 β-turn. Amino acid conjugates of these bicyclic lactams were synthesized on solid supports following a 9-fluorenylmethoxycarbonyl (FMOC) protection strategy on Wang-Merrifield 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′-tetramethyluronium hexafluorophosphate (HATU). The final compounds were cleaved from the resin and obtained as N-acetylated methyl esters or benzyl amides. 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DIPEA picrate has ε = 14500 (a 10-5 M solution has A = 0.145). For further details, see ref.[12] Google Scholar 17 Procedure: A few resin beads were sampled and washed several times with ethanol. The sample was then placed in a vial and 1 drop of a 10% solution of DIPEA in DMF and 1 drop of 1% 2,4,6-trinitrobenzenesulfonic acid (TNBS) in DMF were added. The sample was then viewed under a microscope and colour changes were noted. The TNBS test is considered to be positive (presence of free amino groups) when the resin beads turn orange or red within 1 min and negative (no free amino groups) when the beads remain colourless. For further details, see ref.[13] Google Scholar Citing Literature Volume1999, Issue2February 1999Pages 379-388 ReferencesRelatedInformation
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