One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade
Abstract Vanillin is a key organoleptic component in vanilla, one of the most important natural flavors in the industry. The limited supply of natural vanilla, extracted from cured vanilla beans, elevates the commercial value of ‘natural’‐labeled vanillin, producible by microbial conversion of natur...
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Online Access: | http://dx.doi.org/10.1002/adsc.202301454 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202301454 |
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crwiley:10.1002/adsc.202301454 2024-06-02T07:57:40+00:00 One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade Kim, Hong‐Gon Jang, Youngho Shin, Jong‐Shik 2024 http://dx.doi.org/10.1002/adsc.202301454 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202301454 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Advanced Synthesis & Catalysis volume 366, issue 8, page 1877-1887 ISSN 1615-4150 1615-4169 journal-article 2024 crwiley https://doi.org/10.1002/adsc.202301454 2024-05-03T10:48:07Z Abstract Vanillin is a key organoleptic component in vanilla, one of the most important natural flavors in the industry. The limited supply of natural vanilla, extracted from cured vanilla beans, elevates the commercial value of ‘natural’‐labeled vanillin, producible by microbial conversion of natural precursors such as ferulic acid, eugenol, isoeugenol, lignin, and glucose. However, cellular toxicity and undesirable overoxidation of vanillin remain challenges to the microbial methods. Here, we developed a one‐pot enzymatic conversion of capsaicinoids to vanillin by retracing the biosynthetic pathway found in Capsicum plants. The enzyme cascade consists of the hydrolysis of capsaicinoids by immobilized lipase B from Candida antarctica (CALB) and the oxidative deamination of the resulting vanillylamine by ω‐transaminase from Paracoccus denitrificans (PDTA). Process optimization of individual enzyme reactions was conducted on an analytical scale, enabling>95% reaction yield of vanillin from capsaicinoids in the one‐pot cascade reaction without undesirable accumulation of the oxidation byproduct and the inhibitory reaction intermediate, i. e., vanillic acid and vanillylamine, respectively. To verify practical applicability, we performed a preparative‐scale reaction starting with 1.75 g capsaicinoids and 2.75 g sodium pyruvate at 10 mg/mL CALB and 3 μM PDTA, leading to an 81% reaction yield and a 57% isolation yield. This study is, to the best of our knowledge, the first demonstration of one‐pot production of vanillin from capsaicinoids, which might pave the way for cost‐effective and sustainable access to natural‐labeled vanillin from a renewable feedstock readily available from Capsicum fruits. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Advanced Synthesis & Catalysis |
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English |
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Abstract Vanillin is a key organoleptic component in vanilla, one of the most important natural flavors in the industry. The limited supply of natural vanilla, extracted from cured vanilla beans, elevates the commercial value of ‘natural’‐labeled vanillin, producible by microbial conversion of natural precursors such as ferulic acid, eugenol, isoeugenol, lignin, and glucose. However, cellular toxicity and undesirable overoxidation of vanillin remain challenges to the microbial methods. Here, we developed a one‐pot enzymatic conversion of capsaicinoids to vanillin by retracing the biosynthetic pathway found in Capsicum plants. The enzyme cascade consists of the hydrolysis of capsaicinoids by immobilized lipase B from Candida antarctica (CALB) and the oxidative deamination of the resulting vanillylamine by ω‐transaminase from Paracoccus denitrificans (PDTA). Process optimization of individual enzyme reactions was conducted on an analytical scale, enabling>95% reaction yield of vanillin from capsaicinoids in the one‐pot cascade reaction without undesirable accumulation of the oxidation byproduct and the inhibitory reaction intermediate, i. e., vanillic acid and vanillylamine, respectively. To verify practical applicability, we performed a preparative‐scale reaction starting with 1.75 g capsaicinoids and 2.75 g sodium pyruvate at 10 mg/mL CALB and 3 μM PDTA, leading to an 81% reaction yield and a 57% isolation yield. This study is, to the best of our knowledge, the first demonstration of one‐pot production of vanillin from capsaicinoids, which might pave the way for cost‐effective and sustainable access to natural‐labeled vanillin from a renewable feedstock readily available from Capsicum fruits. |
format |
Article in Journal/Newspaper |
author |
Kim, Hong‐Gon Jang, Youngho Shin, Jong‐Shik |
spellingShingle |
Kim, Hong‐Gon Jang, Youngho Shin, Jong‐Shik One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade |
author_facet |
Kim, Hong‐Gon Jang, Youngho Shin, Jong‐Shik |
author_sort |
Kim, Hong‐Gon |
title |
One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade |
title_short |
One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade |
title_full |
One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade |
title_fullStr |
One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade |
title_full_unstemmed |
One‐Pot Production of Vanillin from Capsaicinoids through a Retrosynthetic Enzyme Cascade |
title_sort |
one‐pot production of vanillin from capsaicinoids through a retrosynthetic enzyme cascade |
publisher |
Wiley |
publishDate |
2024 |
url |
http://dx.doi.org/10.1002/adsc.202301454 https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202301454 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Advanced Synthesis & Catalysis volume 366, issue 8, page 1877-1887 ISSN 1615-4150 1615-4169 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/adsc.202301454 |
container_title |
Advanced Synthesis & Catalysis |
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1800740864693108736 |