Synthesis and Utility of β-Selenol-Phenylalanine for Native Chemical Ligation–Deselenization Chemistry

Lara R. Malins; Richard J. Payne

doi:10.1021/ol3012265

Synthesis and Utility of β-Selenol-Phenylalanine for Native Chemical Ligation–Deselenization Chemistry

Lara R. Malins, Richard J. Payne^*

^*Corresponding author for this work

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

74 Citations (Scopus)

Abstract

An efficient synthetic route to a suitably protected β-selenol- phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.

Original language	English
Pages (from-to)	3142-3145
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	12
Early online date	29 May 2012
DOIs	https://doi.org/10.1021/ol3012265
Publication status	Published - 15 Jun 2012
Externally published	Yes

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10.1021/ol3012265

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title = "Synthesis and Utility of β-Selenol-Phenylalanine for Native Chemical Ligation–Deselenization Chemistry",

abstract = "An efficient synthetic route to a suitably protected β-selenol- phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.",

author = "Malins, {Lara R.} and Payne, {Richard J.}",

year = "2012",

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AU - Payne, Richard J.

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N2 - An efficient synthetic route to a suitably protected β-selenol- phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.

AB - An efficient synthetic route to a suitably protected β-selenol- phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.

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U2 - 10.1021/ol3012265

DO - 10.1021/ol3012265

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SN - 1523-7060

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SP - 3142

EP - 3145

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Synthesis and Utility of β-Selenol-Phenylalanine for Native Chemical Ligation–Deselenization Chemistry

Abstract

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