Synthesis and oligomerization of 10,16-dihydroxyhexadecanoyl esters with different head-groups for the study of CUS1 selectivity

Ignacio  M. San Segundo; Gauthier  M. L. Scavée; Sara  B. R. Pedersen; Nicholas Segerson; Jocelyn  K. C. Rose; Mads H. Clausen

doi:10.1002/ejoc.201900863

Synthesis and oligomerization of 10,16-dihydroxyhexadecanoyl esters with different head-groups for the study of CUS1 selectivity

Ignacio M. San Segundo, Gauthier M. L. Scavée, Sara B. R. Pedersen, Nicholas Segerson, Jocelyn K. C. Rose, Mads H. Clausen^*

^*Corresponding author for this work

Department of Chemistry

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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.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	33
Pages (from-to)	5704-5708
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201900863
Publication status	Published - 2019

Keywords

Cutin synthase
Biochemistry
Substrate selectivity
Enzyme
Polymerization

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@article{8b0ed34751f145c7989b0f53194c9f91,

title = "Synthesis and oligomerization of 10,16-dihydroxyhexadecanoyl esters with different head-groups for the study of CUS1 selectivity",

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.",

keywords = "Cutin synthase, Biochemistry, Substrate selectivity, Enzyme, Polymerization",

author = "{San Segundo}, {Ignacio M.} and Scav{\'e}e, {Gauthier M. L.} and Pedersen, {Sara B. R.} and Nicholas Segerson and Rose, {Jocelyn K. C.} and Clausen, {Mads H.}",

year = "2019",

doi = "10.1002/ejoc.201900863",

language = "English",

volume = "2019",

pages = "5704--5708",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "33",

}

Synthesis and oligomerization of 10,16-dihydroxyhexadecanoyl esters with different head-groups for the study of CUS1 selectivity. / San Segundo, Ignacio M.; Scavée, Gauthier M. L.; Pedersen, Sara B. R. et al.
In: European Journal of Organic Chemistry, Vol. 2019, No. 33, 2019, p. 5704-5708.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Synthesis and oligomerization of 10,16-dihydroxyhexadecanoyl esters with different head-groups for the study of CUS1 selectivity

AU - San Segundo, Ignacio M.

AU - Scavée, Gauthier M. L.

AU - Pedersen, Sara B. R.

AU - Segerson, Nicholas

AU - Rose, Jocelyn K. C.

AU - Clausen, Mads H.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

KW - Cutin synthase

KW - Biochemistry

KW - Substrate selectivity

KW - Enzyme

KW - Polymerization

U2 - 10.1002/ejoc.201900863

DO - 10.1002/ejoc.201900863

M3 - Journal article

SN - 1434-193X

VL - 2019

SP - 5704

EP - 5708

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 33

ER -

Synthesis and oligomerization of 10,16-dihydroxyhexadecanoyl esters with different head-groups for the study of CUS1 selectivity

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Keywords

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