Enantioselective ene‐reduction of <i>E</i>‐2‐cyano‐3‐(furan‐2‐yl) acrylamide by marine and terrestrial fungi and absolute configuration of (<i>R</i>)‐2‐cyano‐3‐(furan‐2‐yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra

Jimenez, David Esteban Quintero; Barreiro, Juliana Cristina; Santos, Fernando Martins dos; Vasconcellos, Suzan Pantaroto de; Porto, André L. M.; Batista, João M.

doi:10.1002/chir.23078

Cited by 11 publications

(3 citation statements)

References 35 publications

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“…ROA is advantageous because a wide range of molecules can be used as VCD, as it also observes vibrations and is sensitive to the chirality of the structure. Occurs in two different behaviors, the first aspect is incident circular polarization (ICP), where the light is circularly polarized in both directions, left or right, and the second is scattered circular polarization (SCP), where an incident light of fixed polarization is used to measuring the intensity of a circularly polarized component of scattered light [18].…”

Section: Raman Optical Activitymentioning

confidence: 99%

Absolute Configuration Determination of Sugar: A Review of the Different Methods

Filho,

Freitas,

Freitas

et al. 2024

IRJPAC

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Determination of the stereochemistry of the stereocenter from the aglyconic part of carbohydrates is always one of the most important tasks for chemistry carbohydrates researchers. The absolute configuration (AC), a challenge for synthetic chemists, has attracted much attention. During the past few decades, many techniques and approaches have been developed to determine the AC of carbohydrates, including methods of X-ray diffraction (XRD), electronic and vibrational circular dichroism (ECD and VCD), Raman optical activity (ROA), nuclear magnetic resonance (NMR) utilizing anisotropic effects of chiral derivatizing agents, and quantum chemical calculations. On the other hand, none of the currently applied techniques can dominate AC determination, since they each have their respective limitations corresponding to the different structural features. This review summarizes most of the techniques and methods commonly used in AC assignment of carbohydrates (but specifically glycosides), in the last decades (2000-2023). GRAPHICAL ABSTRACT

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Section: Raman Optical Activitymentioning

confidence: 99%

Absolute Configuration Determination of Sugar: A Review of the Different Methods

Filho,

Freitas,

Freitas

et al. 2024

IRJPAC

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“…Zhou et al reported that A. sydowii PT-2 isolated from Pu-erh tea degraded theobromine to 3-methylxanthine in a liquid culture through N-7 demethylation [ 124 ]. Also, Jimenez et al reported that A. sydowii CBMAI 935 associated with C. erecta sponge collected from Sao Sebastiao, São Paulo, Brazil, enantioselectively reduced ene of E-2-cyano-3-(furan-2-yl)acrylamide to (R)-2-cyano-3-(furan-2-yl)propanamide with a high yield [ 125 ]. In 2018, Morais et al studied the reduction of α-chloroacetophenones to (S)-alcohols using whole cells of marine-derived A. sydowii CBMAI 935 [ 126 ].…”

Section: Industrial and Biotechnological Applicationsmentioning

confidence: 99%

Secondary Metabolites, Biological Activities, and Industrial and Biotechnological Importance of Aspergillus sydowii

Ibrahim,

Mohamed,

Alsaadi

et al. 2023

Marine Drugs

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Marine-derived fungi are renowned as a source of astonishingly significant and synthetically appealing metabolites that are proven as new lead chemicals for chemical, pharmaceutical, and agricultural fields. Aspergillus sydowii is a saprotrophic, ubiquitous, and halophilic fungus that is commonly found in different marine ecosystems. This fungus can cause aspergillosis in sea fan corals leading to sea fan mortality with subsequent changes in coral community structure. Interestingly, A. sydowi is a prolific source of distinct and structurally varied metabolites such as alkaloids, xanthones, terpenes, anthraquinones, sterols, diphenyl ethers, pyrones, cyclopentenones, and polyketides with a range of bioactivities. A. sydowii has capacity to produce various enzymes with marked industrial and biotechnological potential, including α-amylases, lipases, xylanases, cellulases, keratinases, and tannases. Also, this fungus has the capacity for bioremediation as well as the biocatalysis of various chemical reactions. The current work aimed at focusing on the bright side of this fungus. In this review, published studies on isolated metabolites from A. sydowii, including their structures, biological functions, and biosynthesis, as well as the biotechnological and industrial significance of this fungus, were highlighted. More than 245 compounds were described in the current review with 134 references published within the period from 1975 to June 2023.

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“…Mucor circinelloides , Mucor plumbeus , and Gliomastix masseei were the most versatile strains, showing the highest conversions for all the analyzed substrates. Avoiding an extensive review here, several other works showed the chemoselective reduction of α,β-unsaturated compounds using marine-derived fungi [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

The Family Keeps on Growing: Four Novel Fungal OYEs Characterized

Robescu

Loprete

Gasparotto

et al. 2022

IJMS

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Aiming at expanding the portfolio of Old Yellow Enzymes (OYEs), which have been systematically studied to be employed in the chemical and pharmaceutical industries as useful biocatalysts, we decided to explore the immense reservoir of filamentous fungi. We drew from the genome of the two Ascomycetes Aspergillus niger and Botryotinia fuckeliana four new members of the OYE superfamily belonging to the classical and thermophilic-like subfamilies. The two BfOYEs show wider substrate spectra than the AnOYE homologues, which appear as more specialized biocatalysts. According to their mesophilic origins, the new enzymes neither show high thermostability nor extreme pH optimums. The crystal structures of BfOYE4 and AnOYE8 have been determined, revealing the conserved features of the thermophilic-like subclass as well as unique properties, such as a peculiar N-terminal loop involved in dimer surface interactions. For the classical representatives BfOYE1 and AnOYE2, model structures were built and analyzed, showing surprisingly wide open access to the active site cavities due to a shorter β6-loop and a disordered capping subdomain.

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Enantioselective ene‐reduction of E‐2‐cyano‐3‐(furan‐2‐yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra

Cited by 11 publications

References 35 publications

Absolute Configuration Determination of Sugar: A Review of the Different Methods

Absolute Configuration Determination of Sugar: A Review of the Different Methods

Secondary Metabolites, Biological Activities, and Industrial and Biotechnological Importance of Aspergillus sydowii

The Family Keeps on Growing: Four Novel Fungal OYEs Characterized

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