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Amino acid derived 1,4‐dialkyl substituted imidazolones
Author(s) -
Diness Frederik,
Meldal Morten
Publication year - 2010
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.21359
Subject(s) - chemistry , aldehyde , amino acid , urea , organic chemistry , combinatorial chemistry , catalysis , biochemistry
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.