Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases

Marta Domínguez; Raquel Pequerul; Rosana Alvarez; Joan Giménez-Dejoz; Eszter Birta; Sergio Porté; Ralph Rühl; Xavier Parés; Jaume Farrés; Angel R. de Lera

doi:10.1016/j.tet.2018.03.050

Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases

Marta Domínguez, Raquel Pequerul, Rosana Alvarez, Joan Giménez-Dejoz, Eszter Birta, Sergio Porté, Ralph Rühl, Xavier Parés, Jaume Farrés, Angel R. de Lera

Departament de Bioquímica i de Biologia Molecular

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© 2018 Elsevier Ltd A new synthesis of three apocarotenoids, namely 14′-apo-β-carotenal, 12′-apo-β-carotenal and 10′-apo-β-carotenal, has been achieved that is based on the acyclic cross-metathesis of the hexaene derived from retinal and the corresponding partners. These compounds can be enzymatically converted to their carboxylic acids by the human aldehyde dehydrogenases involved in retinaldehyde oxidation. Their kinetic parameters suggest that these enzymes might play a role in the physiological metabolism of apocarotenoids.

Idioma original	Anglès
Pàgines (de-a)	2567-2574
Revista	Tetrahedron
Volum	74
Número	21
DOIs	https://doi.org/10.1016/j.tet.2018.03.050
Estat de la publicació	Publicada - 24 de maig 2018

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10.1016/j.tet.2018.03.050

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title = "Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases",

abstract = "{\textcopyright} 2018 Elsevier Ltd A new synthesis of three apocarotenoids, namely 14′-apo-β-carotenal, 12′-apo-β-carotenal and 10′-apo-β-carotenal, has been achieved that is based on the acyclic cross-metathesis of the hexaene derived from retinal and the corresponding partners. These compounds can be enzymatically converted to their carboxylic acids by the human aldehyde dehydrogenases involved in retinaldehyde oxidation. Their kinetic parameters suggest that these enzymes might play a role in the physiological metabolism of apocarotenoids.",

author = "Marta Dom{\'i}nguez and Raquel Pequerul and Rosana Alvarez and Joan Gim{\'e}nez-Dejoz and Eszter Birta and Sergio Port{\'e} and Ralph R{\"u}hl and Xavier Par{\'e}s and Jaume Farr{\'e}s and {de Lera}, {Angel R.}",

year = "2018",

month = may,

day = "24",

doi = "10.1016/j.tet.2018.03.050",

language = "English",

volume = "74",

pages = "2567--2574",

journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases

AU - Domínguez, Marta

AU - Pequerul, Raquel

AU - Alvarez, Rosana

AU - Giménez-Dejoz, Joan

AU - Birta, Eszter

AU - Porté, Sergio

AU - Rühl, Ralph

AU - Parés, Xavier

AU - Farrés, Jaume

AU - de Lera, Angel R.

PY - 2018/5/24

Y1 - 2018/5/24

N2 - © 2018 Elsevier Ltd A new synthesis of three apocarotenoids, namely 14′-apo-β-carotenal, 12′-apo-β-carotenal and 10′-apo-β-carotenal, has been achieved that is based on the acyclic cross-metathesis of the hexaene derived from retinal and the corresponding partners. These compounds can be enzymatically converted to their carboxylic acids by the human aldehyde dehydrogenases involved in retinaldehyde oxidation. Their kinetic parameters suggest that these enzymes might play a role in the physiological metabolism of apocarotenoids.

AB - © 2018 Elsevier Ltd A new synthesis of three apocarotenoids, namely 14′-apo-β-carotenal, 12′-apo-β-carotenal and 10′-apo-β-carotenal, has been achieved that is based on the acyclic cross-metathesis of the hexaene derived from retinal and the corresponding partners. These compounds can be enzymatically converted to their carboxylic acids by the human aldehyde dehydrogenases involved in retinaldehyde oxidation. Their kinetic parameters suggest that these enzymes might play a role in the physiological metabolism of apocarotenoids.

U2 - 10.1016/j.tet.2018.03.050

DO - 10.1016/j.tet.2018.03.050

M3 - Article

SN - 0040-4020

VL - 74

SP - 2567

EP - 2574

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases

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