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Issue 7, 2015
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Efficient chemoenzymatic synthesis of lipo-chitin oligosaccharides as plant growth promoters

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Abstract

Lipo-chitin oligosaccharides (Nod and Myc LCOs) are molecules involved in symbiotic phenomena in the plant kingdom. They play a major role in the process of atmospheric nitrogen fixation and mineral soil nutrients uptake both in legumes and in non-legumes, and are active at extremely low concentrations down to the nano- and even picomolar range. These compounds contain various substitutions along the oligosaccharide backbone of the molecule including an essential fatty acid on the non-reducing unit and are considered as environmentally-friendly fertilizers. Currently, chemical synthesis cannot produce precursors of Nod and Myc LCOs at a large scale and an in vitro chemoenzymatic pathway is presented here as a new and efficient method for preparing quantities of these high-value oligosaccharides. VC1280 (Vibrio cholerae) is a chitin deacetylase (CD) capable of regioselectively cleaving an acetate from the non-reducing penultimate N-acetyl-D-glucosaminyl (GlcNAc) unit of chitin oligosaccharides (COs). This provides a free amino group which can be further N-acylated with a fatty-acid chain to give analogues of LCOs. Alternatively, the non-reducing GlcNAc unit can be removed by β-N-acetylglucosaminidase treatment, followed by N-acylation to give natural LCOs. VC1280 CD was produced in the periplasm of E. coli. Under the conditions used, 120 mg of the pure enzyme was recovered from 1 L of culture medium. For the first time, in vitro production of a library of natural LCOs as well as their analogues has been carried out at a preparative scale from biosourced chitin oligosaccharides constituting an approach of major interest for sustainable agriculture.

Graphical abstract: Efficient chemoenzymatic synthesis of lipo-chitin oligosaccharides as plant growth promoters

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Publication details

The article was received on 23 Mar 2015, accepted on 15 May 2015 and first published on 18 May 2015


Article type: Paper
DOI: 10.1039/C5GC00623F
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Citation: Green Chem., 2015,17, 3923-3930
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    Efficient chemoenzymatic synthesis of lipo-chitin oligosaccharides as plant growth promoters

    R. Chambon, G. Despras, A. Brossay, B. Vauzeilles, D. Urban, J.-M. Beau, S. Armand, S. Cottaz and S. Fort, Green Chem., 2015, 17, 3923
    DOI: 10.1039/C5GC00623F

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