TY - JOUR
T1 - Oxidative Modification of Tryptophan-Containing Peptides
AU - Petersen, Jonas
AU - Christensen, Katrine E.
AU - Nielsen, Mathias T.
AU - Mortensen, Kim T.
AU - Komnatnyy, Vitaly V.
AU - Nielsen, Thomas Eiland
AU - Qvortrup, Katrine
N1 - doi: 10.1021/acscombsci.8b00014
PY - 2018
Y1 - 2018
N2 - We herein present a broadly useful method for the chemoselective modification of a wide range of tryptophan-containing peptides. Exposing a tryptophan-containing peptide to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a selective cyclodehydration between the peptide backbone and the indole side chain of tryptophan to form a fully conjugated indolyl-oxazole moiety. The modified peptides show a characteristic and significant emission maximum at 425 nm, thus making the method a useful strategy for fluorescence labeling.
AB - We herein present a broadly useful method for the chemoselective modification of a wide range of tryptophan-containing peptides. Exposing a tryptophan-containing peptide to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a selective cyclodehydration between the peptide backbone and the indole side chain of tryptophan to form a fully conjugated indolyl-oxazole moiety. The modified peptides show a characteristic and significant emission maximum at 425 nm, thus making the method a useful strategy for fluorescence labeling.
U2 - 10.1021/acscombsci.8b00014
DO - 10.1021/acscombsci.8b00014
M3 - Tidsskriftartikel
C2 - 29719155
VL - 20
SP - 344
EP - 349
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 6
ER -