Alkaloid Biosynthesis

Leete, Edward

doi:10.1002/9780470122778.ch9

Cited by 5 publications

(2 citation statements)

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“…The TIA biosynthetic pathway begins with the coupling of the isoprene building blocks dimethylallyl pyrophosphate (DMAP) and isopentenyl pyrophosphate (IPP) to form geranyl diphosphate (GPP). Reduction in GPP to geraniol followed by a multi‐enzyme conversion results in secologanin, a common precursor for many plant natural products (Leete, 1967; Verpoorte et al, 1997). A Pictet‐Spengler reaction coupling secologanin and tryptamine (derived from decarboxylation of tryptophan by tryptophan decarboxylase [TDC]) by strictosidine reductase (STR) yields strictosidine.…”

Section: Introductionmentioning

confidence: 99%

Metabolomics analysis reveals both plant variety and choice of hormone treatment modulate vinca alkaloid production in Catharanthus roseus

2020

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Many plant-derived secondary metabolites have chemical properties that give them therapeutic value for the treatment of cancers, hypertension, and other illnesses (Balunas & Kinghorn, 2005). In the medicinal plant Catharanthus roseus (L.) G. Don, the terpene indole alkaloid (TIA) family of natural products includes many valuable medicinal compounds such as the clinically used antineoplastic agents vinblastine and vincristine, as well as the antihypertensive agent ajmalicine (Figure 1). Vinblastine and vincristine, used in the

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Section: Introductionmentioning

confidence: 99%

Metabolomics analysis reveals both plant variety and choice of hormone treatment modulate vinca alkaloid production in Catharanthus roseus

2020

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“…It has been known for more than a century and is widely used in many areas of organic chemistry [24][25][26][27][28][29][30][31][32] . It has also been frequently proposed in many biosynthetic pathways, especially for alkaloids biosynthesis 33,34 . This reaction utilizes a nonenolizable aldehyde, a secondary amine and an enolizable carbonyl compound as starting materials, and affords useful βamino-carbonyl products in one step.…”

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Three-component radical homo Mannich reaction

et al. 2021

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Aliphatic amine, especially tertiary aliphatic amine, is one of the most popular functionalities found in pharmaceutical agents. The Mannich reaction is a classical and widely used transformation for the synthesis of β-amino-carbonyl products. Due to an ionic nature of the mechanism, the Mannich reaction can only use non-enolizable aldehydes as substrates, which significantly limits the further applications of this powerful approach. Here we show, by employing a radical process, we are able to utilize enolizable aldehydes as substrates and develop the three-component radical homo Mannich reaction for the streamlined synthesis of γ-amino-carbonyl compounds. The electrophilic radicals are generated from thiols via the desulfurization process facilitated by visible-light, and then add to the electron-rich double bonds of the in-situ formed enamines to provide the products in a single step. The broad scope, mild conditions, high functional group tolerance, and modularity of this metal-free approach for the synthesis of complex tertiary amine scaffolds will likely be of great utility to chemists in both academia and industry.

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Aromatische Aminos�uren im Stoffwechsel h�herer Pflanzen

Kindl

1971

Naturwissenschaften

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Alkaloid Biosynthesis

Cited by 5 publications

References 207 publications

Metabolomics analysis reveals both plant variety and choice of hormone treatment modulate vinca alkaloid production in Catharanthus roseus

Metabolomics analysis reveals both plant variety and choice of hormone treatment modulate vinca alkaloid production in Catharanthus roseus

Three-component radical homo Mannich reaction

Aromatische Aminos�uren im Stoffwechsel h�herer Pflanzen

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