Synthesis of enantiopure structured triacylglycerols

Björn Kristinsson; Kaisa M. Linderborg; Heikki Kallio; Gudmundur G. Haraldsson

doi:10.1016/j.tetasy.2013.11.015

Synthesis of enantiopure structured triacylglycerols

Björn Kristinsson, Kaisa M. Linderborg, Heikki Kallio, Gudmundur G. Haraldsson

Faculty of Physical Sciences

University of Iceland

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.

Original language	English
Pages (from-to)	125-132
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	25
Issue number	2
DOIs	https://doi.org/10.1016/j.tetasy.2013.11.015
Publication status	Published - 31 Jan 2014

Bibliographical note

Funding Information: Novozymes AS in Denmark is acknowledged for the lipase and Dr. Sigridur Jonsdottir at University of Iceland for accurate MS measurements. Funding from the Academy of Finland (grant 251623 ) is acknowledged.

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title = "Synthesis of enantiopure structured triacylglycerols",

abstract = "The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.",

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note = "Funding Information: Novozymes AS in Denmark is acknowledged for the lipase and Dr. Sigridur Jonsdottir at University of Iceland for accurate MS measurements. Funding from the Academy of Finland (grant 251623 ) is acknowledged.",

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doi = "10.1016/j.tetasy.2013.11.015",

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T1 - Synthesis of enantiopure structured triacylglycerols

AU - Kristinsson, Björn

AU - Linderborg, Kaisa M.

AU - Kallio, Heikki

AU - Haraldsson, Gudmundur G.

N1 - Funding Information: Novozymes AS in Denmark is acknowledged for the lipase and Dr. Sigridur Jonsdottir at University of Iceland for accurate MS measurements. Funding from the Academy of Finland (grant 251623 ) is acknowledged.

PY - 2014/1/31

Y1 - 2014/1/31

N2 - The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.

AB - The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.

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U2 - 10.1016/j.tetasy.2013.11.015

DO - 10.1016/j.tetasy.2013.11.015

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

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ER -

Synthesis of enantiopure structured triacylglycerols

Abstract

Bibliographical note

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