First Asymmetric Reduction of Isatin by Marine-Derived Fungi

Birolli, Willian Garcia; Ferrreira, Irlon M.; Jimenez, David Esteban Quintero; Silva, Bianca N. M.; Silva, Bárbara V.; Pinto, Ângelo C.; Porto, André L. M.

doi:10.21577/0103-5053.20160256

Cited by 6 publications

(8 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To confirm the enhanced PET on the SiNW tip, two typical dyes, indigo and isatin, were used as the model molecules for LDI-MS detection. Both indigo and isatin molecules have a redox moiety, which can undergo multistep electron-transfer processes. , SiNWs-1, SiNWs-2, Si wafer, and their thermally oxidized counterparts were used as LDI substrates. To compare the energy- and electron-transfer abilities among these materials, the relative laser energy was manipulated from the lower level (e.g., 64% of maximum laser energy) to a higher degree (e.g., 88% of maximum laser energy).…”

Section: Results and Discussionmentioning

confidence: 99%

Tip-Enhanced Photoinduced Electron Transfer and Ionization on Vertical Silicon Nanowires

Chen

Wang

et al. 2018

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

Nanostructured semiconductors are one of the most potent candidates for matrix-free laser desorption/ionization mass spectrometric (LDI-MS) analysis of low-molecular-weight molecules. Herein, the enhanced photoinduced electron transfer and LDI on the tip of a vertical silicon nanowire (SiNW) array were investigated. Theoretical simulation and LDI detection of indigo and isatin molecules in negative ion mode revealed that the electric field can be enhanced on the tip end of SiNWs, thereby promoting the energy and electron transfer to the analytes adsorbed on the tip of SiNWs. On the basis of this finding, a tip-contact sampling method coupled with LDI-MS detection was established. In this strategy, the tip of SiNWs can be regarded as microextraction heads for the sampling of molecules when they come in contact with analytes. Impression of skin, tissue, and pericarp on the vertical SiNW array can effectively transfer endogenous metabolites or exogenous substances onto the tip. Upon laser irradiation, the adsorbed molecules on the SiNW tip can be efficiently ionized and detected in negative ion mode because of the tip-enhanced electron transfer and LDI effect. We believe this work may significantly expand the application of LDI-MS in various fields.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Tip-Enhanced Photoinduced Electron Transfer and Ionization on Vertical Silicon Nanowires

Chen

Wang

et al. 2018

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…Asymmetric reductions of isatins to 3-hydroxoxindoles have been reported that provide comparison compounds for chiroptical assignments of 17 and 18 . 29,30,31…”

Section: Resultsmentioning

confidence: 99%

“…Asymmetric reductions of isatins to 3-hydroxoxindoles have been reported that provide comparison compounds for chiroptical assignments of 17 and 18 . − For example, isatin undergoes enzyme-catalyzed reduction in the presence of a carbonyl reductase derived from Candida parapsilosis to give (+)-( R )-dioxindole in 21% ee . ( R )-5-Methyldioxindole ( 19 , 38.5% ee), prepared by Sonderegger and co-workers using partial asymmetric hydrogenation of 20 (H 2 , Pt supported on Al 2 O 3 -(−)-cinchonidine, Scheme ), exhibited an ECD spectrum dominated by a negative Cotton effect (CE) (λ 237 nm, −41, arbitrary units of ellipticity) and a second CE of opposite sign at longer wavelength (λ 264, +12.5) .…”

Section: Resultsmentioning

confidence: 99%

Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD

Salib

Molinski

2018

J. Org. Chem.

View full text Add to dashboard Cite

Six new cyclopenta[g]indoles were isolated from a West Australian sponge, Trikentrion flabelliforme Hentschel, 1912, and their structures elucidated by integrated spectroscopic analysis. The compounds are analogues of previously described trikentrins, herbindoles, and trikentramides from related Axinellid sponges. The assignment of absolute configuration of the new compounds was carried out largely by comparative analysis of specific rotation, calculated and measured ECD, and exploiting van't Hoff's principle of optical superposition. Five of the new compounds were chemically interconverted to establish their stereochemical relationships, leading to a simple chiroptical mnemonic for assignment of the this family of chiral indoles. The first biosynthetic hypothesis is advanced to explain the origin of the trikentrin-herbinole family and proposes a pyrrole-carboxylic thioester-initiated polyketide synthase mechanism.

show abstract

“…CBMAI 1679, and A. sydowii CBMAI 935). These experiments showed that the reduction of nitrogenated compounds, which are usually consumed as nutrient source in biocatalytic processes by whole cells, could be performed ( y = 26–37%, 18–66% ee S -enantiomer, phosphate buffer pH 7.0, 32°C, 130 rpm, 3–7 days) (Birolli et al, 2017).…”

Section: Whole-cell Processesmentioning

confidence: 99%

Applications of Marine-Derived Microorganisms and Their Enzymes in Biocatalysis and Biotransformation, the Underexplored Potentials

2019

View full text Add to dashboard Cite

Biodiversity has been explored in the search for novel enzymes, including forests, savannas, tundras, deserts, and finally the sea. Marine microorganisms and their enzymes are capable of being active in high-salt concentration, large range of temperature, and high incidence of light and pressure, constituting an important source of unique biocatalysts. This review presents studies employing whole-cell processes of marine bacteria and fungi, aiming for new catalysts for different reactions in organic synthesis, such as reduction, oxidation, hydroxylation, hydrolysis, elimination, and conjugation. Genomics and protein engineering studies were also approached, and reactions employing isolated enzymes from different classes (oxidoreductases, hydrolases, lyases, and ligases) were described and summarized. Future biotechnological studies and process development should focus on molecular biology for the obtention of enzymes with interesting, fascinating and enhanced properties, starting from the exploration of microorganisms from the marine environment. This review approaches the literature about the use of marine-derived bacteria, fungi, and their enzymes for biocatalytic reactions of organic compounds, promoting a discussion about the possibilities of these microorganisms in the synthesis of different substances.

show abstract

First Asymmetric Reduction of Isatin by Marine-Derived Fungi

Cited by 6 publications

References 15 publications

Tip-Enhanced Photoinduced Electron Transfer and Ionization on Vertical Silicon Nanowires

Tip-Enhanced Photoinduced Electron Transfer and Ionization on Vertical Silicon Nanowires

Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD

Applications of Marine-Derived Microorganisms and Their Enzymes in Biocatalysis and Biotransformation, the Underexplored Potentials

Contact Info

Product

Resources

About