Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B
Abstract A protocol for the analysis of the positional distribution of fatty acids (FA) in solid triacylglycerols (TAG) was developed using sn ‐1(3) selective alcoholysis catalyzed by immobilized Candida antarctica lipase B (CALB). One part by weight of solid fat and ten parts by weight of ethanol (...
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crwiley:10.1007/s11746-014-2481-7 2024-06-02T07:58:19+00:00 Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B Watanabe, Yomi Sato, Shinichi Sera, Saiko Sato, Chiemi Yoshinaga, Kazuaki Nagai, Toshiharu Sato, Ryota Iwasaka, Hiroaki Aki, Tsunehiro 2014 http://dx.doi.org/10.1007/s11746-014-2481-7 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-014-2481-7 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 91, issue 8, page 1323-1330 ISSN 0003-021X 1558-9331 journal-article 2014 crwiley https://doi.org/10.1007/s11746-014-2481-7 2024-05-03T11:20:11Z Abstract A protocol for the analysis of the positional distribution of fatty acids (FA) in solid triacylglycerols (TAG) was developed using sn ‐1(3) selective alcoholysis catalyzed by immobilized Candida antarctica lipase B (CALB). One part by weight of solid fat and ten parts by weight of ethanol (99.5 %) were warmed to liquefy the fat. After adding 0.44 parts by weight of CALB, the mixture was shaken at 50 °C for 10 min then at 30 °C for 2.8 h. The recovery of 2‐MAG after the 3‐h transesterification reaction was ca . 85 % of the maximum theoretical yield (33 mol%), with the loss of 15 % attributable to the acyl migration from sn ‐2 to sn ‐1(3). The recovery was similar to that of the solvent‐free alcoholysis of structured lipids, 1,3‐dipalmitoyl, 2‐oleoyl glycerol and 1,3‐dioleoyl, 2‐palmitoyl glycerol, conducted at 30 °C for 3 h. In contrast, the acyl migration from sn ‐1(3) to sn ‐2 was hardly observed. Because the detected acyl migration was only in the direction of sn ‐2 to sn ‐1(3), and not vice versa, it is proposed to determine the FA composition of the sn ‐2 position of TAG by the gas chromatographic analysis of 2‐MAG fraction recovered from the enzymatic reaction mixture, and the FA composition of sn ‐1(3) position by a mass balance using the FA composition of TAG and of the sn ‐2 position as inputs. The procedure was successfully applied to palm oil and shea butter, and docosahexaenoic acid (DHA)‐rich single cell oil from Aurantiochytrium sp. KH105 for the first time. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of the American Oil Chemists' Society 91 8 1323 1330 |
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Wiley Online Library |
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English |
description |
Abstract A protocol for the analysis of the positional distribution of fatty acids (FA) in solid triacylglycerols (TAG) was developed using sn ‐1(3) selective alcoholysis catalyzed by immobilized Candida antarctica lipase B (CALB). One part by weight of solid fat and ten parts by weight of ethanol (99.5 %) were warmed to liquefy the fat. After adding 0.44 parts by weight of CALB, the mixture was shaken at 50 °C for 10 min then at 30 °C for 2.8 h. The recovery of 2‐MAG after the 3‐h transesterification reaction was ca . 85 % of the maximum theoretical yield (33 mol%), with the loss of 15 % attributable to the acyl migration from sn ‐2 to sn ‐1(3). The recovery was similar to that of the solvent‐free alcoholysis of structured lipids, 1,3‐dipalmitoyl, 2‐oleoyl glycerol and 1,3‐dioleoyl, 2‐palmitoyl glycerol, conducted at 30 °C for 3 h. In contrast, the acyl migration from sn ‐1(3) to sn ‐2 was hardly observed. Because the detected acyl migration was only in the direction of sn ‐2 to sn ‐1(3), and not vice versa, it is proposed to determine the FA composition of the sn ‐2 position of TAG by the gas chromatographic analysis of 2‐MAG fraction recovered from the enzymatic reaction mixture, and the FA composition of sn ‐1(3) position by a mass balance using the FA composition of TAG and of the sn ‐2 position as inputs. The procedure was successfully applied to palm oil and shea butter, and docosahexaenoic acid (DHA)‐rich single cell oil from Aurantiochytrium sp. KH105 for the first time. |
format |
Article in Journal/Newspaper |
author |
Watanabe, Yomi Sato, Shinichi Sera, Saiko Sato, Chiemi Yoshinaga, Kazuaki Nagai, Toshiharu Sato, Ryota Iwasaka, Hiroaki Aki, Tsunehiro |
spellingShingle |
Watanabe, Yomi Sato, Shinichi Sera, Saiko Sato, Chiemi Yoshinaga, Kazuaki Nagai, Toshiharu Sato, Ryota Iwasaka, Hiroaki Aki, Tsunehiro Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B |
author_facet |
Watanabe, Yomi Sato, Shinichi Sera, Saiko Sato, Chiemi Yoshinaga, Kazuaki Nagai, Toshiharu Sato, Ryota Iwasaka, Hiroaki Aki, Tsunehiro |
author_sort |
Watanabe, Yomi |
title |
Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B |
title_short |
Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B |
title_full |
Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B |
title_fullStr |
Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B |
title_full_unstemmed |
Enzymatic Analysis of Positional Distribution of Fatty Acids in Solid Fat by 1,3‐Selective Transesterification with Candida antarctica Lipase B |
title_sort |
enzymatic analysis of positional distribution of fatty acids in solid fat by 1,3‐selective transesterification with candida antarctica lipase b |
publisher |
Wiley |
publishDate |
2014 |
url |
http://dx.doi.org/10.1007/s11746-014-2481-7 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-014-2481-7 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the American Oil Chemists' Society volume 91, issue 8, page 1323-1330 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-014-2481-7 |
container_title |
Journal of the American Oil Chemists' Society |
container_volume |
91 |
container_issue |
8 |
container_start_page |
1323 |
op_container_end_page |
1330 |
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1800741620013858816 |