Jump to main content
Jump to site search

Issue 8, 2012
Previous Article Next Article

Cysteine as a sustainable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: biomimetic synthesis of L-ergothioneine in water

Author affiliations

Abstract

Biomass-derived cysteine was used as a sustainable sulfur source for the synthesis of rare sulfur-containing amino acids, such as L-ergothioneine (4), which might be a new vitamin, and various L- or D-2-thiohistidine compounds. Key in this simple, one-pot two-step procedure in water is a bromine-induced regioselective introduction of cysteine followed by a novel thermal cleavage reaction in the presence of thiols, a safer alternative to hazardous red phosphorus. Besides avoiding hazardous sulfur reagents, the new protecting-group-free approach reduces drastically the total number of steps, compared to described procedures. The main drawback, i.e. handling of liquid bromine as an activating and oxidizing reagent in water, was addressed by evaluating four alternative methods using in situ generation of bromine or HOBr, and first encouraging results are described.

Graphical abstract: Cysteine as a sustainable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: biomimetic synthesis of l-ergothioneine in water

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 12 Mar 2012, accepted on 31 May 2012 and first published on 20 Jun 2012


Article type: Paper
DOI: 10.1039/C2GC35367A
Citation: Green Chem., 2012,14, 2256-2265
  •   Request permissions

    Cysteine as a sustainable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: biomimetic synthesis of L-ergothioneine in water

    I. Erdelmeier, S. Daunay, R. Lebel, L. Farescour and J. Yadan, Green Chem., 2012, 14, 2256
    DOI: 10.1039/C2GC35367A

Search articles by author