Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry

Lara R. Malins; Andrew M. Giltrap; Luke J. Dowman; Richard J. Payne

doi:10.1021/acs.orglett.5b00597

Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry

Lara R. Malins, Andrew M. Giltrap, Luke J. Dowman, Richard J. Payne^*

^*Corresponding author for this work

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

33 Citations (Scopus)

Abstract

The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner's aldehyde. The utility of this amino acid in peptide ligation-desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.

Original language	English
Pages (from-to)	2070-2073
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	9
Early online date	10 Apr 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b00597
Publication status	Published - 1 May 2015
Externally published	Yes

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title = "Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry",

abstract = "The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner's aldehyde. The utility of this amino acid in peptide ligation-desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.",

author = "Malins, {Lara R.} and Giltrap, {Andrew M.} and Dowman, {Luke J.} and Payne, {Richard J.}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

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AU - Malins, Lara R.

AU - Giltrap, Andrew M.

AU - Dowman, Luke J.

AU - Payne, Richard J.

PY - 2015/5/1

Y1 - 2015/5/1

N2 - The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner's aldehyde. The utility of this amino acid in peptide ligation-desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.

AB - The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner's aldehyde. The utility of this amino acid in peptide ligation-desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.

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U2 - 10.1021/acs.orglett.5b00597

DO - 10.1021/acs.orglett.5b00597

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SP - 2070

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry

Abstract

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