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 Citationer (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.

Originalsprog	Dansk
Tidsskrift	ACS Combinatorial Science
Vol/bind	20
Udgave nummer	6
Sider (fra-til)	344-349
Antal sider	6
ISSN	2156-8952
DOI	https://doi.org/10.1021/acscombsci.8b00014
Status	Udgivet - 11 jun. 2018

Adgang til dokumentet

10.1021/acscombsci.8b00014

Citationsformater

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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,

day = "11",

doi = "10.1021/acscombsci.8b00014",

language = "Dansk",

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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 - 2018/6/11

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 -