on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal
Oxidative stress enhances lipid peroxidation (LPO) implicated in cancer promotion and progression. (E)-4-Hydroxynon-2-enal 1 (trans-4-hydroxy-2-nonenal, HNE) is one of the most abundant products of LPO. Reactions of HNE with DNA and proteins are responsible for its mutagenic and toxic effects. On th...
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ftciteseerx:oai:CiteSeerX.psu:10.1.1.415.9018 2023-05-15T13:40:22+02:00 on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal Marek Komisarski Zuzanna Kaczmarska Jarosław T. Kuśmierek The Pennsylvania State University CiteSeerX Archives 2009 application/pdf http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.415.9018 http://www.actabp.pl/pdf/1_2009/189.pdf en eng http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.415.9018 http://www.actabp.pl/pdf/1_2009/189.pdf Metadata may be used without restrictions as long as the oai identifier remains attached to it. http://www.actabp.pl/pdf/1_2009/189.pdf E)-4-hydroxynon-2-enal (4-HNE) synthesis 4-HNE enantiomers asymmetric synthesis Candida antarctica lipase lipid text 2009 ftciteseerx 2016-01-08T03:38:44Z Oxidative stress enhances lipid peroxidation (LPO) implicated in cancer promotion and progression. (E)-4-Hydroxynon-2-enal 1 (trans-4-hydroxy-2-nonenal, HNE) is one of the most abundant products of LPO. Reactions of HNE with DNA and proteins are responsible for its mutagenic and toxic effects. On the other hand, HNE is regarded as a key molecule in stress mediated cell cycle signaling. LPO generates racemic HNE (rac-1); however, it is expected that the individual enantiomers will behave differently in their interactions with cell components. The study of HNE stereochemistry in its chemical and biochemical interactions is hindered by the lack of expedient methods for preparation of pure enantiomers. This study presents one step synthesis of HNE in a cross-metathesis reaction between the commercially available oct-1-en-3-ol and acrolein in the presence of 2nd generation Grubbs catalyst. The use in the metathesis reaction of enantiomers of oct-1-en-3-ol obtained via Candida antarctica lipase resolution of the racemate allowed us to prepare of 4-(R)- and 4-(S)-enantiomers of HNE (R-1 and S-1, respectively) with excellent optical purity (97.5 and 98.4 % ee, respectively) and good chemical yields (70%). Text Antarc* Antarctica Unknown |
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English |
topic |
E)-4-hydroxynon-2-enal (4-HNE) synthesis 4-HNE enantiomers asymmetric synthesis Candida antarctica lipase lipid |
spellingShingle |
E)-4-hydroxynon-2-enal (4-HNE) synthesis 4-HNE enantiomers asymmetric synthesis Candida antarctica lipase lipid Marek Komisarski Zuzanna Kaczmarska Jarosław T. Kuśmierek on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal |
topic_facet |
E)-4-hydroxynon-2-enal (4-HNE) synthesis 4-HNE enantiomers asymmetric synthesis Candida antarctica lipase lipid |
description |
Oxidative stress enhances lipid peroxidation (LPO) implicated in cancer promotion and progression. (E)-4-Hydroxynon-2-enal 1 (trans-4-hydroxy-2-nonenal, HNE) is one of the most abundant products of LPO. Reactions of HNE with DNA and proteins are responsible for its mutagenic and toxic effects. On the other hand, HNE is regarded as a key molecule in stress mediated cell cycle signaling. LPO generates racemic HNE (rac-1); however, it is expected that the individual enantiomers will behave differently in their interactions with cell components. The study of HNE stereochemistry in its chemical and biochemical interactions is hindered by the lack of expedient methods for preparation of pure enantiomers. This study presents one step synthesis of HNE in a cross-metathesis reaction between the commercially available oct-1-en-3-ol and acrolein in the presence of 2nd generation Grubbs catalyst. The use in the metathesis reaction of enantiomers of oct-1-en-3-ol obtained via Candida antarctica lipase resolution of the racemate allowed us to prepare of 4-(R)- and 4-(S)-enantiomers of HNE (R-1 and S-1, respectively) with excellent optical purity (97.5 and 98.4 % ee, respectively) and good chemical yields (70%). |
author2 |
The Pennsylvania State University CiteSeerX Archives |
format |
Text |
author |
Marek Komisarski Zuzanna Kaczmarska Jarosław T. Kuśmierek |
author_facet |
Marek Komisarski Zuzanna Kaczmarska Jarosław T. Kuśmierek |
author_sort |
Marek Komisarski |
title |
on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal |
title_short |
on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal |
title_full |
on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal |
title_fullStr |
on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal |
title_full_unstemmed |
on-line at: www.actabp.pl Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal |
title_sort |
on-line at: www.actabp.pl practical highly enantioselective synthesis of (r)- and (s)-(e)-4-hydroxynon-2-enal |
publishDate |
2009 |
url |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.415.9018 http://www.actabp.pl/pdf/1_2009/189.pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
http://www.actabp.pl/pdf/1_2009/189.pdf |
op_relation |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.415.9018 http://www.actabp.pl/pdf/1_2009/189.pdf |
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Metadata may be used without restrictions as long as the oai identifier remains attached to it. |
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1766132915769442304 |