4-Amino-1, 2-dithiolane-4-carboxylic acid (Adt) as cysteine conformationally restricted analogue. Synthetic protocol for Adt containing peptides

…, M Nalli, F Pinnen, D Rossi, G Lucente

Index: Morera, Enrico; Nalli, Marianna; Pinnen, Francesco; Rossi, Domenico; Lucente, Gino Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 14 p. 1585 - 1588

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Citation Number: 17

Abstract

An efficient and versatile protocol to incorporate the achiral and Cα, α-tetrasubstituted 4- amino-1, 2-dithiolane-4-carboxylic acid Adt (1) residue into peptides is described. The 2, 2- bis [(benzylthio) methyl] glycine N-carboxy anhydride (5) was found to be the key reactive intermediate from which both Boc-Adt-OMe (8) and the glutathione analogue H-Glu (-Adt-Gly- OH)-OH (12) can be obtained.