Synthesis of Nα-Fmoc N,N′-bis-Boc-5-, 6- and 8-guanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid (5-GTIC, 6-GTIC and 8-GTIC)

Beatrice Severino; Vincenzo Santagada; Francesco Frecentese; Elisa Perissutti; Sara Terracciano; Ferdinando Fiorino; Donatella Cirillo; Severo Salvadori; Gianfranco Balboni; Giuseppe Caliendo

doi:10.1055/s-2004-834875

PAPER

Synthesis of N ^α-Fmoc N,N′-bis-Boc-5-, 6- and 8-guanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid (5-GTIC, 6-GTIC and 8-GTIC)

Beatrice Severino^a, Vincenzo Santagada*^a, Francesco Frecentese^a, Elisa Perissutti^a, Sara Terracciano^a, Ferdinando Fiorino^a, Donatella Cirillo^a, Severo Salvadori^b, Gianfranco Balboni^b, Giuseppe Caliendo^a
^a Dipartimento di Chimica Farmaceutica e Tossicologica, Università di Napoli ‘Federico II’, Via D. Montesano 49, 80131 Napoli, Italy
Fax: +39(81)678649; e-Mail: santagad@unina.it;
^b Dipartimento di Scienze Farmaceutiche, Università di Ferrara, via Fossato di Mortara, 4100 Ferrara, Italy

Abstract

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Abstract

N ^α-Fmoc N,N′-bis-Boc-5-, 6- and 8-guanyl-Tic-OH (5-, 6- and 8-GTIC), three conformationally constrained amino acids with basic properties, have been synthesized by microwave irradiation. These amino acids combine the basic features of arginine with the aromatic features of phenylalanine and can be utilized as functional tools in peptide-based structure-activity studies.

Key words

unconventional amino acid - microwave - synthesis - GTIC

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References

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Synthesis of N α-Fmoc N,N′-bis-Boc-5-, 6- and 8-guanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid (5-GTIC, 6-GTIC and 8-GTIC)

Synthesis of N ^α-Fmoc N,N′-bis-Boc-5-, 6- and 8-guanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid (5-GTIC, 6-GTIC and 8-GTIC)