Amino acid derived 1,4-dialkyl substituted imidazolones
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Amino acid derived 1,4-dialkyl substituted imidazolones. / Diness, Frederik; Meldal, Morten Peter.
In: Biopolymers, Vol. 94, No. 2, 11.03.2010, p. 236-241.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Amino acid derived 1,4-dialkyl substituted imidazolones
AU - Diness, Frederik
AU - Meldal, Morten Peter
N1 - Keywords: amino acids, imidazolones, urea bonds, N-acyliminum, Pictet-Spengler reaction
PY - 2010/3/11
Y1 - 2010/3/11
N2 - 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.
AB - 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.
KW - Amino Acids
KW - Catalysis
KW - Copper
KW - Imidazoles
KW - Molecular Structure
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1002/bip.21359
DO - 10.1002/bip.21359
M3 - Journal article
C2 - 20225297
VL - 94
SP - 236
EP - 241
JO - Biopolymers
JF - Biopolymers
SN - 0006-3525
IS - 2
ER -
ID: 34206032