Expression, crystallization and preliminary X-ray analysis of McbB, a multifunctional enzyme involved in β-carboline skeleton biosynthesis

Wang, Hua; Zhang, Huaidong; Mi, Yanling; Ju, Jianhua; Chen, Qi; Zhang, Houjin

doi:10.1107/s2053230x14018743

Cited by 2 publications

(1 citation statement)

References 22 publications

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“…(2014) The crystal structure of mcbB was also analyzed and its catalytic mechanism discussed by another group [252]. (2013) The Oikawa group reported then the identification of the biosynthetic gene clusters of quinocarcin and the antitumor antibiotic SF-1739, which share a common type II tetracyclic tetrahydroisoquinoline (THIQ)-pyrrolidine core scaffold.…”

Section: Biogenetic Studiesmentioning

confidence: 99%

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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Section: Biogenetic Studiesmentioning

confidence: 99%

The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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Iodine‐DMSO‐Catalyzed Chemoselective Biomimetic Aromatization of Tetrahydro‐β‐carbolines‐3‐carboxylic Acid: Mechanism Study with DFT‐Calculation

et al. 2019

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A new protocol for the chemoselective aromatization of tetrahydro-β-carboline-3-carboxylic acids to direct biomimetic one step synthesis of β-carboline-3-carboxylic acids 2 A-L using catalytic amount of I 2 in DMSO/H + produces very good yield. This method was also successfully extended for the aromatiza-tion of tetrahydro-β-carboline-3-methyl esters 5 A-G as well as one-step synthesis of Marinacarbolines-D analog, respectively. Further, the mechanism and role of iodine-DMSO in aromatization has been studied by Density Functional Theory Calculation.[a] S.

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Expression, crystallization and preliminary X-ray analysis of McbB, a multifunctional enzyme involved in β-carboline skeleton biosynthesis

Cited by 2 publications

References 22 publications

The Pictet-Spengler Reaction Updates Its Habits

The Pictet-Spengler Reaction Updates Its Habits

Iodine‐DMSO‐Catalyzed Chemoselective Biomimetic Aromatization of Tetrahydro‐β‐carbolines‐3‐carboxylic Acid: Mechanism Study with DFT‐Calculation

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