4-Amino-1,2-dithiolane-4-carboxylic acid (Adt) as cysteine conformationally restricted analogue. Synthetic protocol for Adt containing peptides.
An efficient and versatile protocol to incorporate the achiral and C(alpha,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.
Morera
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Centro di Studio per la Chimica del Farmaco del CNR c/o Dipartimento di Studi Farmaceutici, Università degli Studi di Roma La Sapienza, Italy.
Nalli
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Pinnen
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Rossi
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D
Lucente
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D000596:Amino Acids / Q000737:chemistry*; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry*; D005978:Glutathione / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D013876:Thiophenes / Q000737:chemistry*
C416078:4-amino-1,2-dithiolane-4-carboxylic acid; D000596:Amino Acids; D007202:Indicators and Reagents; D009842:Oligopeptides; D013876:Thiophenes; D005978:Glutathione; D003545:Cysteine