A New Convenient Route for the Synthesis of DOPA Peptides

✍ Scribed by Nakonieczna, Lucja ;Przychodzeń, Witold ;Chimiak, Andrzej

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 436 KB
• Volume: 1994
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199419941017

✦ Synopsis

Abstract

The tert‐butyldimethylsilyl group as the catechol protective group of DOPA (compound 1a), Boc‐DOPA (compound 1b) and DOPA esters (compounds 2a–c) is introduced. The compounds 2a–c and 1b are used as the starting substrates for the synthesis of the protected N‐terminal DOPA and C‐terminal DOPA dipeptides, 3a–d and 4a–f, respectively. Optimal conditions for deprotection are presented. Acidolysis of the fully protected DOPA peptides 3a–d and 4a–f gives quantitatively the pure DOPA dipeptides in one step.