The Pictet-Spengler Reaction Still on Stage

Ingallina, Cinzia; D’Acquarica, Ilaria; Monache, Giuliano Delle; Ghirga, Francesca; Quaglio, Deborah; Ghirga, Patrizio; Berardozzi, Simone; Marković, Violeta; Botta, Bruno

doi:10.2174/1381612822666151231100247

Cited by 27 publications

(12 citation statements)

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“…Additionally, a handful of new enzymes carrying the Pictet‐Spengler reaction such as salsolinol synthase, McbB from Marinactinospora thermotolerans , deacetylisoipecoside synthase, and deacetylipecoside synthase, two novel NCSs from Argemone mexicana (AmNCS1, AmNCS2) and one new NCS from Corydalis saxicola have recently been identified. The development in the understanding of these enzymes will further enrich the biocatalytic synthesis of a myriad of alkaloids with diverse pharmaceutical functions ,…”

Section: Pictet‐spenglerasesmentioning

confidence: 99%

Biocatalyzed C−C Bond Formation for the Production of Alkaloids

2018

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Traditional methods of chemical synthesis of alkaloids exhibit various problems such as lack of enantioselectivity, the use of toxic chemical and intermediates, and multiple numbers of synthetic steps. Consequently, various enzymatic methods for the formation of CÀC bonds in the alkaloid skeleton have been developed. Herein, we report advances achieved in the enzymatic or chemo-enzymatic synthesis of pharmaceutically important alkaloids that employ three CÀC bond forming enzymes: two Pictet-Spenglerases and the oxidative CÀC bond forming flavoenzyme Berberine Bridge Enzyme. Protein engi-neering studies, improving the substrate scope of these enzymes, and thereby leading to the synthesis of non-natural alkaloids possessing higher or newer pharmacological activities, are also discussed. Furthermore, the integration of these biocatalysts with other enzymes, in multi-enzymatic cascades for the enantioselective synthesis of alkaloids, is also reviewed. Current results suggest that these enzymes hold great promise for the generation of CÀC bonds in the selective synthesis of alkaloid compounds possessing diverse pharmacological properties.

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Section: Pictet‐spenglerasesmentioning

confidence: 99%

Biocatalyzed C−C Bond Formation for the Production of Alkaloids

2018

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“…Few years ago, we celebrated in a paper [1] the long-lasting presence on stage of the Pictet-Spengler (P-S) cyclization as one of the most direct, efficient, and variable synthetic method for the construction of important privileged pharmacophores, such as tetrahydroisoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic architectures embodying them.…”

Section: Introductionmentioning

confidence: 99%

“…In the Act I of this tribute [1], we put in evidence some facets of the reaction, from the link to the biogenetic pathways of natural products, mainly alkaloids, to the challenge of the stereochemical…”

Section: Introductionmentioning

confidence: 99%

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The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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“…This review aims to provide an overview of the asymmetric PSR, in which the chirality arises from optically pure amines or carbonyl compounds both from natural sources and from asymmetric syntheses to assembly the reaction partners. However, external asymmetric induction by chiral catalysts on symmetric derivatives can also be used in PSR [6][7][8][9][10], but these examples will not be covered in this review. For over a century, it has been used for the synthesis of a large variety of aza-heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

The Chiral Pool in the Pictet–Spengler Reaction for the Synthesis of β-Carbolines

Dalpozzo

2016

Molecules

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Abstract:The Pictet-Spengler reaction (PSR) is the reaction of a β-arylethylamine with an aldehyde or ketone, followed by ring closure to give an aza-heterocycle. When the β-arylethylamine is tryptamine, the product is a β-carboline, a widespread skeleton in natural alkaloids. In the natural occurrence, these compounds are generally enantiopure, thus the asymmetric synthesis of these compounds have been attracting the interest of organic chemists. This review aims to give an overview of the asymmetric PSR, in which the chirality arises from optically pure amines or carbonyl compounds both from natural sources and from asymmetric syntheses to assemble the reaction partners.

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The Pictet-Spengler Reaction Still on Stage

Cited by 27 publications

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Biocatalyzed C−C Bond Formation for the Production of Alkaloids

Biocatalyzed C−C Bond Formation for the Production of Alkaloids

The Pictet-Spengler Reaction Updates Its Habits

The Chiral Pool in the Pictet–Spengler Reaction for the Synthesis of β-Carbolines

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