Biomimetic Synthesis of Ornithine/Arginine and Lysine‐Derived Alkaloids: Selected Examples

Poupon, Erwan; Salame, Rim; Yan, Lok‐Hang

doi:10.1002/9783527634606.ch1

Cited by 6 publications

(3 citation statements)

References 161 publications

(111 reference statements)

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“…L-Lys is the homologue of L-Orn, a precursor of pyrrolidine, tropane, and pyrrolizidine alkaloids. The extra methylene group in Lys participates in forming 6-membered piperidine rings, while Orn participates in forming 5-membered pyrrolizidine rings ( Dewick, 2001 ; Poupon et al, 2011 ). Biosynthetic pathways of several potential Lys-derived alkaloids have been proposed based on tracer experiments with labeled precursors ( Leistner and Spenser, 1973 and references therein).…”

Section: Biosynthesis Of Lys-derived Alkaloidsmentioning

confidence: 99%

Quinolizidine alkaloid biosynthesis: recent advances and future prospects

Bunsupa¹,

Yamazaki²,

Saito³

2012

Front. Plant Sci.

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Lys-derived alkaloids, including piperidine, quinolizidine, indolizidine, and lycopodium alkaloids, are widely distributed throughout the plant kingdom. Several of these alkaloids have beneficial properties for humans and have been used in medicine. However, the molecular mechanisms underlying the biosynthesis of these alkaloids are not well understood. In the present article, we discuss recent advances in our understanding of Lys-derived alkaloids, especially the biochemistry, molecular biology, and biotechnology of quinolizidine alkaloid (QA) biosynthesis. We have also highlighted Lys decarboxylase (LDC), the enzyme that catalyzes the first committed step of QA biosynthesis and answers a longstanding question about the molecular entity of LDC activity in plants. Further prospects using current advanced technologies, such as next-generation sequencing, in medicinal plants have also been discussed.

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Section: Biosynthesis Of Lys-derived Alkaloidsmentioning

confidence: 99%

Quinolizidine alkaloid biosynthesis: recent advances and future prospects

Bunsupa¹,

Yamazaki²,

Saito³

2012

Front. Plant Sci.

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“…Anatabine biosynthesis differs significantly from that of nicotine, as both of its rings originate from the pyridine-nucleotide pathway, once nicotinic acid is converted to 3,6dihydronicotinic acid. Although no anatabine-specific enzymes have been discovered, radiolabeling biomimetic studies suggest that it is further decarboxylated to 1,2-dihydropyridine and 2,5-dihydropyridine [27]. These two intermediates can either react together to form 3,6-dihydroanatabine, or the same effect can occur from dimerization of 2,5-dihydopyridine itself.…”

Section: Alkaloidsmentioning

confidence: 99%

Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species

László

Kaminski

Guan³

et al. 2022

Molecules

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There is an increasingly urgent call to shift industrial processes from fossil fuel feedstock to sustainable bio-based resources. This change becomes of high importance considering new budget requirements for a carbon-neutral economy. Such a transformation can be driven by traditionally used plants that are able to produce large amounts of valuable biologically relevant secondary metabolites. Tobacco plants can play a leading role in providing value-added products in remote areas of the world. In this study, we propose a non-exhaustive list of compounds with potential economic interest that can be sourced from the tobacco plant. In order to optimize extraction methodologies, we first analyzed their physico-chemical properties using rapid solubility tests and high-resolution microfractionation techniques. Next, to identify an optimal extraction for a selected list of compounds, we compared 13 different extraction method–solvent combinations. We proceeded with profiling some of these compounds in a total of six varieties from Nicotiana tabacum and Nicotiana rustica species, identifying the optimal variety for each. The estimated expected yields for each of these compounds demonstrate that tobacco plants can be a superior source of valuable compounds with diverse applications beyond nicotine. Among the most interesting results, we found high variability of anatabine content between species and varieties, ranging from 287 to 1699 µg/g. In addition, we found that CGA (1305 µg/g) and rutin (7910 µg/g) content are orders of magnitude lower in the Burley variety as compared to all others.

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“…Pyridoxal-5′-phosphate (PLP)-dependent enzymes are widespread in cellular processes and intimately associated with biosynthetic pathways involving amino compounds . From actively participating in the biosynthesis of amino acids − to being involved in the biosynthesis or degradation of aminosugars, polyamines − , and alkaloids, the PLP-dependent enzymes are characterized by the plethora of chemical reactions they catalyze.…”

Section: Introductionmentioning

confidence: 99%

Discovery, Engineering, and Synthetic Application of Transaminase Biocatalysts

et al. 2017

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Transaminases have attracted considerable interest in their use as biocatalysts for the synthesis of compounds containing chiral amine units, which are widespread within the pharmaceutical, agrochemical, and fine chemical industry. Recent developments in enzyme- and process-engineering have expedited their use in asymmetric synthesis; however, industrial applications are still hindered by a number of factors, including equilibrium thermodynamics, product inhibition, and poor substrate tolerance. Detailed and comprehensive approaches to each of these challenges have been reported during the last two decades; the most representative enzyme discovery and screening strategies, protein and equilibrium engineering, and immobilization techniques are reviewed herein. Furthermore, we present a detailed look into the applications of transaminases for the synthesis of a variety of amine-containing compounds and the integration of transaminases into multienzymatic systems that allow access to a variety of highly complex products for the end user.

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Biomimetic Synthesis of Ornithine/Arginine and Lysine‐Derived Alkaloids: Selected Examples

Cited by 6 publications

References 161 publications

Quinolizidine alkaloid biosynthesis: recent advances and future prospects

Quinolizidine alkaloid biosynthesis: recent advances and future prospects

Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species

Discovery, Engineering, and Synthetic Application of Transaminase Biocatalysts

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