Site-selective three-component reaction for dual-functionalization of peptides

Henrik Kofoed Munch; Jakob Ewald Rasmussen; Gina Popa; Jørn Bolstad Christensen; K.J. Jensen

doi:10.1039/c3cc38673b

Site-selective three-component reaction for dual-functionalization of peptides

Henrik Kofoed Munch, Jakob Ewald Rasmussen, Gina Popa, Jørn Bolstad Christensen, K.J. Jensen

Department of Chemistry

6 Citations (Scopus)

Abstract

A site-selective dual-functionalization of peptides is presented, involving readily available maleimides as well as N-hydroxylamines. The modification proceeds through a three component 1,3-dipolar cycloaddition, forming a stable product. This was exemplified by the one-pot attachment of two molecular imaging moieties to a tumor binding cyclic peptide, and was extended to the conjugation of a DOTA chelator to a 12 kDa protein.

Original language	English
Journal	Chemical Communications
Volume	49
Issue number	19
Pages (from-to)	1936-1938
Number of pages	3
ISSN	1359-7345
DOIs	https://doi.org/10.1039/c3cc38673b
Publication status	Published - 7 Feb 2013

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abstract = "A site-selective dual-functionalization of peptides is presented, involving readily available maleimides as well as N-hydroxylamines. The modification proceeds through a three component 1,3-dipolar cycloaddition, forming a stable product. This was exemplified by the one-pot attachment of two molecular imaging moieties to a tumor binding cyclic peptide, and was extended to the conjugation of a DOTA chelator to a 12 kDa protein.",

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AU - Munch, Henrik Kofoed

AU - Rasmussen, Jakob Ewald

AU - Popa, Gina

AU - Christensen, Jørn Bolstad

AU - Jensen, K.J.

PY - 2013/2/7

Y1 - 2013/2/7

N2 - A site-selective dual-functionalization of peptides is presented, involving readily available maleimides as well as N-hydroxylamines. The modification proceeds through a three component 1,3-dipolar cycloaddition, forming a stable product. This was exemplified by the one-pot attachment of two molecular imaging moieties to a tumor binding cyclic peptide, and was extended to the conjugation of a DOTA chelator to a 12 kDa protein.

AB - A site-selective dual-functionalization of peptides is presented, involving readily available maleimides as well as N-hydroxylamines. The modification proceeds through a three component 1,3-dipolar cycloaddition, forming a stable product. This was exemplified by the one-pot attachment of two molecular imaging moieties to a tumor binding cyclic peptide, and was extended to the conjugation of a DOTA chelator to a 12 kDa protein.

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U2 - 10.1039/c3cc38673b

DO - 10.1039/c3cc38673b

M3 - Journal article

C2 - 23370690

AN - SCOPUS:84873673638

SN - 1359-7345

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SP - 1936

EP - 1938

JO - Chemical Communications

JF - Chemical Communications

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ER -

Site-selective three-component reaction for dual-functionalization of peptides

Abstract

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