Synthesis and Oligomerization of 10,16-Dihydroxyhexadecanoyl Esters with Different Head-Groups for the Study of CUS1 Selectivity

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Abstract

Members of the CUS family, suspected to be responsible for cutin polymerization, have shown in vitro activity towards sn-2 glyceryl ester (2-MAGs). To assess the selectivity of CUS enzymes towards esters with different headgroups, the CUS1 mediated in vitro polymerization of four monomers of 10,16-dihydroxyhexadecanoic acid was investigated. Our results demonstrated that CUS1 is more selective towards sn-2 glyceryl ester, reinforcing the hypothesis that 2-MAGs are the monomeric precursors of the plant polyester cutin. Additionally, the absence of oxygen atoms in the headgroup negatively impacts the efficiency of polymerization.

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San Segundo, I. M., Scavée, G. M. L., Pedersen, S. B. R., Segerson, N., Rose, J. K. C., & Clausen, M. H. (2019). Synthesis and Oligomerization of 10,16-Dihydroxyhexadecanoyl Esters with Different Head-Groups for the Study of CUS1 Selectivity. European Journal of Organic Chemistry, 2019(33), 5704–5708. https://doi.org/10.1002/ejoc.201900863

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