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

Authors
Morera, E Nalli, M Pinnen, F Rossi, D Lucente, G
Citation
E. Morera et al., 4-amino-1,2-dithiolane-4-carboxylic acid (Adt) as cysteine conformationally restricted analogue. Synthetic protocol for Adt containing peptides, BIOORG MED, 10(14), 2000, pp. 1585-1588
Citations number
31
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
10
Issue
14
Year of publication
2000
Pages
1585 - 1588
Database
ISI
SICI code
0960-894X(20000717)10:14<1585:4A(ACC>2.0.ZU;2-2
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) r esidue into peptides is described. The 2,2-bis[(benzylthio)methyl]glycine N -carboxy anhydride (5) was found to be the key reactive intermediate from w hich both Boc-Adt-OMe (8) and the glutathione analogue H-Glu(-Adt-Gly-OH)-O H (12) can be obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.