Oxidative Modification of Tryptophan-Containing Peptides

Jonas Petersen; Katrine E. Christensen; Mathias T. Nielsen; Kim T. Mortensen; Vitaly V. Komnatnyy; Thomas Eiland Nielsen; Katrine Qvortrup

doi:10.1021/acscombsci.8b00014

Oxidative Modification of Tryptophan-Containing Peptides

Jonas Petersen, Katrine E. Christensen, Mathias T. Nielsen, Kim T. Mortensen, Vitaly V. Komnatnyy, Thomas Eiland Nielsen, Katrine Qvortrup

4 Citations (Scopus)

Abstract

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.

Original language	Danish
Journal	ACS Combinatorial Science
Volume	20
Issue number	6
Pages (from-to)	344-349
Number of pages	6
ISSN	2156-8952
DOIs	https://doi.org/10.1021/acscombsci.8b00014
Publication status	Published - 11 Jun 2018

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10.1021/acscombsci.8b00014

Cite this

@article{446de26051364b2f80b264920ca3232e,

title = "Oxidative Modification of Tryptophan-Containing Peptides",

abstract = "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.",

author = "Jonas Petersen and Christensen, {Katrine E.} and Nielsen, {Mathias T.} and Mortensen, {Kim T.} and Komnatnyy, {Vitaly V.} and Nielsen, {Thomas Eiland} and Katrine Qvortrup",

note = "doi: 10.1021/acscombsci.8b00014",

year = "2018",

month = jun,

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doi = "10.1021/acscombsci.8b00014",

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journal = "ACS Combinatorial Science",

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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 - 2018/6/11

Y1 - 2018/6/11

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

SN - 2156-8952

VL - 20

SP - 344

EP - 349

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

IS - 6

ER -