Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media

Tom  Willemse; Karolien  Van Imp; Rebecca Jane Miriam Goss; Herman W.T. Van Vlijmen; Wim  Schepens; Bert U.W.  Maes; Steven Ballet

doi:10.1002/cctc.201500190

Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media

Tom Willemse, Karolien Van Imp , Rebecca Jane Miriam Goss, Herman W.T. Van Vlijmen, Wim Schepens, Bert U.W. Maes , Steven Ballet

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

Abstract

The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with much potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that whilst asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross-coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.

Original language	English
Pages (from-to)	2055-2070
Journal	ChemCatChem
Volume	7
Issue number	14
Early online date	29 Jun 2015
DOIs	https://doi.org/10.1002/cctc.201500190
Publication status	Published - 13 Jul 2015

Keywords

Amino acids
C-C coupling
Palladium
Peptides
Homogenous catalysis

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10.1002/cctc.201500190

RJMG7415
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Willemse, T., Van Imp, K., Goss, R. J. M., Van Vlijmen, H. W. T., Schepens, W., Maes, B. U. W. and Ballet, S. (2015), Suzuki–Miyaura Diversification of Amino Acids and Dipeptides in Aqueous Media. ChemCatChem, 7: 2055–2070, which has been published in final form at http://dx.doi.org/10.1002/cctc.201500190
Accepted author manuscript, 1.23 MB

Cite this

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title = "Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media",

abstract = "The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with much potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that whilst asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross-coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.",

keywords = "Amino acids, C-C coupling, Palladium, Peptides, Homogenous catalysis",

author = "Tom Willemse and {Van Imp}, Karolien and Goss, {Rebecca Jane Miriam} and {Van Vlijmen}, {Herman W.T.} and Wim Schepens and Maes, {Bert U.W.} and Steven Ballet",

note = "The authors gratefully acknowledge the IWT Flanders and Janssen Pharmaceutica for financial support of T.W. This work is supported by the Scientific Research Network (WOG) “Sustainable chemistry for the synthesis of fine chemicals” of the Research Foundation - Flanders (FWO). ",

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doi = "10.1002/cctc.201500190",

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T1 - Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media

AU - Willemse, Tom

AU - Van Imp , Karolien

AU - Goss, Rebecca Jane Miriam

AU - Van Vlijmen, Herman W.T.

AU - Schepens, Wim

AU - Maes , Bert U.W.

AU - Ballet, Steven

N1 - The authors gratefully acknowledge the IWT Flanders and Janssen Pharmaceutica for financial support of T.W. This work is supported by the Scientific Research Network (WOG) “Sustainable chemistry for the synthesis of fine chemicals” of the Research Foundation - Flanders (FWO).

PY - 2015/7/13

Y1 - 2015/7/13

N2 - The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with much potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that whilst asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross-coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.

AB - The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with much potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that whilst asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross-coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.

KW - Amino acids

KW - C-C coupling

KW - Palladium

KW - Peptides

KW - Homogenous catalysis

UR - http://onlinelibrary.wiley.com/doi/10.1002/cctc.201500190/suppinfo

U2 - 10.1002/cctc.201500190

DO - 10.1002/cctc.201500190

M3 - Article

SN - 1867-3880

VL - 7

SP - 2055

EP - 2070

JO - ChemCatChem

JF - ChemCatChem

IS - 14

ER -

Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media

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Keywords

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