A mild method for the synthesis of a novel dehydrobutyrine-containing amino acid

Alexandra M. Webster; Christopher R. Coxon; Alan M. Kenwright; Graham Sandford; Steven L. Cobb

doi:10.1016/j.tet.2014.05.031

A mild method for the synthesis of a novel dehydrobutyrine-containing amino acid

Alexandra M. Webster, Christopher R. Coxon, Alan M. Kenwright, Graham Sandford, Steven L. Cobb^*

^*Corresponding author for this work

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

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Abstract

Dehydrobutyrine is an amino acid that is present in a range of peptide natural products. Reaction of pentafluoropyridine with threonine and subsequent E1cb-type elimination allowed the preparation of novel dehydrobutyrine- containing amino acids under mild conditions.

Original language	English
Pages (from-to)	4661-4667
Number of pages	7
Journal	Tetrahedron
Volume	70
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2014.05.031
Publication status	Published - 5 Aug 2014

Keywords

Amino acid
Dehydrobutyrine
Nucleophilic aromatic substitution
Pentafluoropyridine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A mild method for the synthesis of a novel dehydrobutyrine-containing amino acid",

abstract = "Dehydrobutyrine is an amino acid that is present in a range of peptide natural products. Reaction of pentafluoropyridine with threonine and subsequent E1cb-type elimination allowed the preparation of novel dehydrobutyrine- containing amino acids under mild conditions.",

keywords = "Amino acid, Dehydrobutyrine, Nucleophilic aromatic substitution, Pentafluoropyridine",

author = "Webster, {Alexandra M.} and Coxon, {Christopher R.} and Kenwright, {Alan M.} and Graham Sandford and Cobb, {Steven L.}",

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AU - Webster, Alexandra M.

AU - Coxon, Christopher R.

AU - Kenwright, Alan M.

AU - Sandford, Graham

AU - Cobb, Steven L.

PY - 2014/8/5

Y1 - 2014/8/5

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AB - Dehydrobutyrine is an amino acid that is present in a range of peptide natural products. Reaction of pentafluoropyridine with threonine and subsequent E1cb-type elimination allowed the preparation of novel dehydrobutyrine- containing amino acids under mild conditions.

KW - Amino acid

KW - Dehydrobutyrine

KW - Nucleophilic aromatic substitution

KW - Pentafluoropyridine

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U2 - 10.1016/j.tet.2014.05.031

DO - 10.1016/j.tet.2014.05.031

M3 - Article

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SN - 0040-4020

VL - 70

SP - 4661

EP - 4667

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

A mild method for the synthesis of a novel dehydrobutyrine-containing amino acid

Abstract

Keywords

ASJC Scopus subject areas

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