Trifluoroethanethiol: An Additive for Efficient One-Pot Peptide Ligation−​Desulfurization Chemistry

Native chemical ligation followed by desulfur­ization is a powerful strategy for the assembly of proteins. Here we describe the development of a high-yielding, one-pot ligation−​desulfur­ization protocol that uses trifluoro­ethane­thiol (TFET) as a novel thiol additive. The synthetic utility of this...

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Published inJournal of the American Chemical Society Vol. 136; no. 23; pp. 8161 - 8164
Main Authors Thompson, Robert E, Liu, Xuyu, Alonso-García, Noelia, Pereira, Pedro José Barbosa, Jolliffe, Katrina A, Payne, Richard J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.06.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Chromatography, High Pressure Liquid
Insect Proteins - chemical synthesis
Insect Proteins - chemistry
Mass Spectrometry
Physical Sciences
Science & Technology
Trifluoroethanol - analogs & derivatives
Trifluoroethanol - chemistry
PROLINE LIGATION
ERYTHROPOIETIN
NATIVE CHEMICAL LIGATION
GLYCOPROTEINS
CYSTEINE
DESELENIZATION
PHENYLALANINE
GLYCOPEPTIDES
PROTEIN-SYNTHESIS
HIGHLY EFFICIENT
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Summary:Native chemical ligation followed by desulfur­ization is a powerful strategy for the assembly of proteins. Here we describe the development of a high-yielding, one-pot ligation−​desulfur­ization protocol that uses trifluoro­ethane­thiol (TFET) as a novel thiol additive. The synthetic utility of this TFET-enabled methodology is demonstrated by the efficient multi-step one-pot syntheses of two tick-derived proteins, chimadanin and madanin-1, without the need for any intermediary purification.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja502806r