Solid-Phase Synthesis of Biocompatible N-Heterocyclic Carbene–Pd Catalysts Using a Sub-monomer Approach

Durgadas Cherukaraveedu; Paul Cowling; Gavin Birch; Mark Bradley; Annamaria Lilienkampf

doi:10.1039/C9OB00716D

Solid-Phase Synthesis of Biocompatible N-Heterocyclic Carbene–Pd Catalysts Using a Sub-monomer Approach

Durgadas Cherukaraveedu, Paul Cowling, Gavin Birch, Mark Bradley, Annamaria Lilienkampf

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

Abstract

Taking inspiration from the assembly of so-called peptoids (N-alkylglycine oligomers) we present a new synthetic methodology whereby N-heterocyclic carbene (NHC) based Pd ligands were assembled using a sub-monomer approach and loaded with Pd via solid-phase synthesis. This allowed the rapid generation a library of NHC–palladium catalysts that were readily functionalised to allow bioconjugation. These catalysts were able to rapidly activate a caged fluorophore and ‘switch-on’ an anticancer prodrug in 3D cell culture.

Original language	English
Journal	Organic & Biomolecular chemistry
Early online date	8 May 2019
DOIs	https://doi.org/10.1039/C9OB00716D
Publication status	E-pub ahead of print - 8 May 2019

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10.1039/C9OB00716D

20190508 Lillienkampf NHCPd catalyst library_PUREAccepted author manuscript, 1.79 MBLicence: Creative Commons: Attribution (CC-BY)

http://pubs.rsc.org/en/Content/ArticleLanding/2019/OB/C9OB00716D

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title = "Solid-Phase Synthesis of Biocompatible N-Heterocyclic Carbene–Pd Catalysts Using a Sub-monomer Approach",

abstract = "Taking inspiration from the assembly of so-called peptoids (N-alkylglycine oligomers) we present a new synthetic methodology whereby N-heterocyclic carbene (NHC) based Pd ligands were assembled using a sub-monomer approach and loaded with Pd via solid-phase synthesis. This allowed the rapid generation a library of NHC–palladium catalysts that were readily functionalised to allow bioconjugation. These catalysts were able to rapidly activate a caged fluorophore and {\textquoteleft}switch-on{\textquoteright} an anticancer prodrug in 3D cell culture.",

author = "Durgadas Cherukaraveedu and Paul Cowling and Gavin Birch and Mark Bradley and Annamaria Lilienkampf",

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AU - Cherukaraveedu, Durgadas

AU - Cowling, Paul

AU - Birch, Gavin

AU - Bradley, Mark

AU - Lilienkampf, Annamaria

PY - 2019/5/8

Y1 - 2019/5/8

N2 - Taking inspiration from the assembly of so-called peptoids (N-alkylglycine oligomers) we present a new synthetic methodology whereby N-heterocyclic carbene (NHC) based Pd ligands were assembled using a sub-monomer approach and loaded with Pd via solid-phase synthesis. This allowed the rapid generation a library of NHC–palladium catalysts that were readily functionalised to allow bioconjugation. These catalysts were able to rapidly activate a caged fluorophore and ‘switch-on’ an anticancer prodrug in 3D cell culture.

AB - Taking inspiration from the assembly of so-called peptoids (N-alkylglycine oligomers) we present a new synthetic methodology whereby N-heterocyclic carbene (NHC) based Pd ligands were assembled using a sub-monomer approach and loaded with Pd via solid-phase synthesis. This allowed the rapid generation a library of NHC–palladium catalysts that were readily functionalised to allow bioconjugation. These catalysts were able to rapidly activate a caged fluorophore and ‘switch-on’ an anticancer prodrug in 3D cell culture.

U2 - 10.1039/C9OB00716D

DO - 10.1039/C9OB00716D

M3 - Article

SN - 1477-0520

JO - Organic & Biomolecular chemistry

JF - Organic & Biomolecular chemistry

ER -

Solid-Phase Synthesis of Biocompatible N-Heterocyclic Carbene–Pd Catalysts Using a Sub-monomer Approach

Abstract

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