Tyramine Derivatives Catalyze the Aldol Dimerization of Butyraldehyde in the Presence of Escherichia coli.
Tyramine Derivatives Catalyze the Aldol Dimerization of Butyraldehyde in the Presence of Escherichia coli.
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DOI：
10.1002/cbic.202200238
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发表时间：
2022-09-05
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影响因子：
--
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生物胺类有机催化剂已经改变了合成有机化学领域。然而，尽管胺类有机催化在体外用于合成和标记生物分子，但体内的胺类有机催化得到的关注相对较少——尽管这种反应有可能与活细胞接触并修饰细胞代谢物。在此，我们报道了从L -酪氨酸衍生的生物胺在活的大肠杆菌存在下催化丁醛自缩成2 -乙基己烯醛（生产大宗化学品2 -乙基己醇的关键中间体），并且优于目前合成有机化学中使用的许多胺类有机催化剂。此外，我们证明了大肠杆菌的细胞裂解液和高产的胺过量生产者谷氨杆杆菌ATCC 13032在体外催化了这一反应，证明了微生物代谢作为细胞生物相容性反应的有机催化剂的潜力。细菌胺有机催化：从L -酪氨酸衍生的生物胺被发现在大肠杆菌存在下催化丁醛的生物相容性自醛醇二聚化。大肠杆菌和谷氨酸棒状杆菌的细胞裂解物也被发现在体外催化该反应。在生物相容性条件下，产物烯醛通过内源性还原酶还原为2‐乙基己醛。
Biogenic amine organocatalysts have transformed the field of synthetic organic chemistry. Yet despite their use in synthesis and to label biomolecules in vitro, amine organocatalysis in vivo has received comparatively little attention – despite the potential of such reactions to be interfaced with living cells and to modify cellular metabolites. Herein we report that biogenic amines derived from L‐tyrosine catalyze the self‐aldol condensation of butanal to 2‐ethylhexenal – a key intermediate in the production of the bulk chemical 2‐ethylhexanol – in the presence of living Escherichia coli and outperform many amine organocatalysts currently used in synthetic organic chemistry. Furthermore, we demonstrate that cell lysate from E. coli and the prolific amine overproducer Corynebacterium glutamicum ATCC 13032 catalyze this reaction in vitro, demonstrating the potential for microbial metabolism to be used as a source of organocatalysts for biocompatible reactions in cells. Bacterial amine organocatalysis: Biogenic amines derived from L‐tyrosine were found to catalyze the biocompatible self‐aldol dimerization of butanal in the presence of Escherichia coli. Cell lysates from both E. coli and Corynebacterium glutamicum were also found to catalyze this reaction in vitro. Under biocompatible conditions, the product enal was reduced to 2‐ethylhexanal via endogenous reductases.
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影响因子：
8.4
作者：
Spears RJ;Brabham RL;Budhadev D;Keenan T;McKenna S;Walton J;Brannigan JA;Brzozowski AM;Wilkinson AJ;Plevin M;Fascione MA
通讯作者：
Fascione MA
影响因子：
4.1
作者：
Sadler JC;Dennis JA;Johnson NW;Wallace S
通讯作者：
Wallace S
影响因子：
15
作者：
Kunjapur, Aditya M.;Tarasova, Yekaterina;Prather, Kristala L. J.
通讯作者：
Prather, Kristala L. J.
影响因子：
2.3
作者：
Voegtle, Heather L.;Jones, Tappey H.;Snelling, Roy R.
通讯作者：
Snelling, Roy R.
影响因子：
7.7
作者：
Wallace, Stephen;Balskus, Emily P.
通讯作者：
Balskus, Emily P.