Amino acid derived 1,4-dialkyl substituted imidazolones

✍ Scribed by Frederik Diness; Morten Meldal

• Book ID: 101720479
• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Tongue: English
• Weight: 394 KB
• Volume: 94
• Category: Article
• ISSN: 0006-3525
• DOI: 10.1002/bip.21359

✦ Synopsis

Abstract

A general method for synthesis of 1,4‐substituted imidazolones from amino acids on solid support or in solution has been developed. Amino acid derived 3‐Boc‐(1,3)‐oxazinane (Box) protected amino aldehyde building blocks were coupled through urea bonds to the amino terminal of dipeptides or amino acids. Upon acidic release, the aldehyde instantaneously formed the cyclic N‐carbamyliminium ion, which rearranged to the corresponding imidazolone. Under strongly acidic conditions the imidazolones acted as nuclophiles in the Pictet‐Spengler reaction. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 94: 236–241, 2010.