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Amino acid derived 1,4-dialkyl substituted imidazolones

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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.
OriginalsprogEngelsk
TidsskriftBiopolymers
Vol/bind94
Udgave nummer2
Sider (fra-til)236-241
ISSN0006-3525
DOI
StatusUdgivet - 11 mar. 2010

Bibliografisk note

Keywords: amino acids, imidazolones, urea bonds, N-acyliminum, Pictet-Spengler reaction

ID: 34206032