Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.

Lucas Henry; Christoph Schneider; Benedict Mützel; Peter V. Simpson; Christoph Nagel; Katharina Fucke; Ulrich Schatzschneider

doi:10.1039/c4cc07892f

Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.

Lucas Henry, Christoph Schneider, Benedict Mützel, Peter V. Simpson, Christoph Nagel, Katharina Fucke, Ulrich Schatzschneider

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

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Abstract

The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.

Original language	English
Pages (from-to)	15692-15695
Journal	Chemical Communications
Volume	50
Issue number	99
DOIs	https://doi.org/10.1039/c4cc07892f
Publication status	Published - 23 Oct 2014

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Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide
© Royal Society of Chemistry 2014. This work is made available online in accordance with the publisher’s policies. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 1.29 MBLicence: Unspecified

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Katharina Edkins
- K.Edkins@qub.ac.uk
- School of Pharmacy - Visiting Scholar
Person: Academic

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title = "Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.",

abstract = "The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a {"}masked{"} alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.",

author = "Lucas Henry and Christoph Schneider and Benedict M{\"u}tzel and Simpson, {Peter V.} and Christoph Nagel and Katharina Fucke and Ulrich Schatzschneider",

year = "2014",

month = oct,

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doi = "10.1039/c4cc07892f",

language = "English",

volume = "50",

pages = "15692--15695",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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}

Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide. / Henry, Lucas; Schneider, Christoph; Mützel, Benedict; Simpson, Peter V.; Nagel, Christoph; Fucke, Katharina; Schatzschneider, Ulrich.

In: Chemical Communications, Vol. 50, No. 99, 23.10.2014, p. 15692-15695.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.

AU - Henry, Lucas

AU - Schneider, Christoph

AU - Mützel, Benedict

AU - Simpson, Peter V.

AU - Nagel, Christoph

AU - Fucke, Katharina

AU - Schatzschneider, Ulrich

PY - 2014/10/23

Y1 - 2014/10/23

N2 - The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.

AB - The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.

U2 - 10.1039/c4cc07892f

DO - 10.1039/c4cc07892f

M3 - Article

C2 - 25370120

VL - 50

SP - 15692

EP - 15695

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 99

ER -

Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.

Abstract

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Katharina Edkins

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