Discovery of McbB, an Enzyme Catalyzing the β‐Carboline Skeleton Construction in the Marinacarboline Biosynthetic Pathway

Chen, Qi; Ji, Changtao; Song, Yongxiang; Huang, Hongbo; Ma, Junying; Tian, Xinpeng; Ju, Jianhua

doi:10.1002/anie.201303449

Cited by 89 publications

(60 citation statements)

References 27 publications

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“…[72] McbB from Marinactinospora thermotolerans catalyzes the condensation between L-tryptophan ( 70 ) and oxaloacetaldehyde ( 71 ) to produce β-carboline ( 72 ). Although McbB displays a different protein fold from that of strictosidine synthase, site-directed mutagenesis studies of McbB identified Glu97 as the catalytic residue.…”

Section: Condensation Reactionsmentioning

confidence: 99%

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

2017

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Chemical reactions that are named in honor of their true or at least perceived discoverers are known as “name reactions”. This review is a collection of biological representatives of named chemical reactions. Emphasis is placed on reaction types and catalytic mechanisms that showcase both the chemical diversity in natural product biosynthesis as well as the parallels with synthetic organic chemistry. An attempt has been made to describe the enzymatic mechanisms of catalysis within the context of their synthetic counterparts whenever possible and to discuss the mechanistic hypotheses for those reactions that are presently active areas of investigation. This review has been categorized by reaction type, e.g., condensation, nucleophilic addition, reduction and oxidation, substitution, carboxylation, radical-mediated, and rearrangements, which are subdivided by named reactions.

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Section: Condensation Reactionsmentioning

confidence: 99%

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

2017

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“…Particularly, there are nearly 64 identified β‐carboline alkaloids distributed across the eight plant families. Importantly, aromatic β‐carboline natural products (Figure ) eudistomin U, isoeudistomin, flazin, flazinamide, perlolyrine, harmane and harmine exhibit a wide range of biological activities such as antimalarial, antiviral, neuroprotection, anti‐HIV, anticancer, etc. Therefore, there has been considerable interest in the synthesis of β‐carbolines .…”

Section: Introductionmentioning

confidence: 99%

Application of metal free aromatization to total synthesis of perlolyrin, flazin, eudistomin U and harmane

Srinath

Abinaya

Baskar

et al. 2020

Journal of Heterocyclic Chem

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“…Pictet–Spenglerases have also been identified in bacterial secondary metabolism151617. The plant enzymes have a central role in engineered microbial systems for the production of alkaloids1819202122.…”

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confidence: 99%

Enzyme catalysed Pictet-Spengler formation of chiral 1,1’-disubstituted- and spiro-tetrahydroisoquinolines

et al. 2017

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The Pictet–Spengler reaction (PSR) involves the condensation and ring closure between a β-arylethylamine and a carbonyl compound. The combination of dopamine and ketones in a PSR leads to the formation of 1,1′-disubstituted tetrahydroisoquinolines (THIQs), structures that are challenging to synthesize and yet are present in a number of bioactive natural products and synthetic pharmaceuticals. Here we have discovered that norcoclaurine synthase from Thalictrum flavum (TfNCS) can catalyse the PSR between dopamine and unactivated ketones, thus facilitating the facile biocatalytic generation of 1,1′-disubstituted THIQs. Variants of TfNCS showing improved conversions have been identified and used to synthesize novel chiral 1,1′-disubstituted and spiro-THIQs. Enzyme catalysed PSRs with unactivated ketones are unprecedented, and, furthermore, there are no equivalent stereoselective chemical methods for these transformations. This discovery advances the utility of enzymes for the generation of diverse THIQs in vitro and in vivo.

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Discovery of McbB, an Enzyme Catalyzing the β‐Carboline Skeleton Construction in the Marinacarboline Biosynthetic Pathway

Cited by 89 publications

References 27 publications

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

Application of metal free aromatization to total synthesis of perlolyrin, flazin, eudistomin U and harmane

Enzyme catalysed Pictet-Spengler formation of chiral 1,1’-disubstituted- and spiro-tetrahydroisoquinolines

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