An efficient and versatile protocol to incorporate the achiral and C-alpha,C-alpha-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. (C) 2000 Elsevier Science Ltd. All rights reserved.
4-amino-1,2-dithiolane-4-carboxylic acid (Adt) as cysteine conformationally restricted analogue. Synthetic protocol for Adt containing peptides / Morera, Enrico; Nalli, Marianna; Francesco, Pinnen; Rossi, Domenico; Lucente, Gino. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - 10:14(2000), pp. 1585-1588. [10.1016/s0960-894x(00)00281-x]
4-amino-1,2-dithiolane-4-carboxylic acid (Adt) as cysteine conformationally restricted analogue. Synthetic protocol for Adt containing peptides
MORERA, ENRICO;NALLI, Marianna;ROSSI, Domenico;LUCENTE, Gino
2000
Abstract
An efficient and versatile protocol to incorporate the achiral and C-alpha,C-alpha-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. (C) 2000 Elsevier Science Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
