Natural product cercosporin as a bioinspired photocatalyst for the synthesis of peptides containing kynurenine <i>via</i> an energy transfer mechanism

Yuan, Zhenbo; Lu, Liushen; Liu, Meiling; Liu, Xuanzhong; Liu, Chang‐Mei; Yin, Dejing; Zhang, Yan; Rao, Yijian

doi:10.1039/d2gc00116k

Cited by 8 publications

(5 citation statements)

References 75 publications

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“…Moreover, photo-mediated reactions to synthesize non-proteinogenic amino acids and peptides, including the glycosylated amino acids and peptides, exhibit high competence, broad functional group tolerance and great energy-saving performance. [96][97][98] Goddard-Borger's group has developed a photo-mediated Ni-catalyzed cross-coupling reaction of 4-bromophenylalanine 36 or 2-bromotryptophan derivatives 39 with commercially available mannosyl bromide 37 in 72-78 % yields (Scheme 7a). [99] Although tertiary amine could be used as terminal reductant and base in the Ni/photoredox dual catalysis, [100][101] poor result was obtained here when DIPEA was added only.…”

Section: Visible Light-mediated Reductive Coupling Of Halogenated Ami...mentioning

confidence: 99%

“…Since visible light has been considered as one of the most green and renewable energies, photocatalysis has become an appealing noncanonical synthetic method widely applied in redox, [91–92] cross‐coupling, [93–94] and C−H functionalization reactions, [95] for the mild reaction conditions, simple operation, as well as the employment of sustainable light source. Moreover, photo‐mediated reactions to synthesize non‐proteinogenic amino acids and peptides, including the glycosylated amino acids and peptides, exhibit high competence, broad functional group tolerance and great energy‐saving performance [96–98] …”

Section: Multi‐step Glycosylation Of Amino Acidsmentioning

confidence: 99%

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Post‐Modification of Amino Acids and Peptides for the Rapid Synthesis of C‐Glycoamino Acids and C‐Glycopeptides

et al. 2022

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Glycoamino acids and glycoproteins, especially C-glycoamino acids and C-glycoproteins, attract tremendous interests in the realm of biology and chemistry due to their wide occurrence in natural products, excellent pharmacodynamic properties and dynamic stability. Compared with the traditional construction of the amino acid or the glycosyl moiety de novo, postmodification of amino acids and peptides through direct glycosylation reactions constitute a powerful synthetic approach to attaining C-glycoamino acids and C-glycopeptides rapidly on account of the high step-economy, broad functional group tolerance, and conservation of the chirality of the amino acid and glycosyl moieties. In this review, the recent developments in the synthesis of C-glycoamino acids and C-glycopeptides via the post-modification of amino acids and peptides are summarized. Additionally, the important and representative examples, synthetic applications, and crucial mechanism investigations of these glycosylation reactions are also highlighted.

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Section: Visible Light-mediated Reductive Coupling Of Halogenated Ami...mentioning

confidence: 99%

Section: Multi‐step Glycosylation Of Amino Acidsmentioning

confidence: 99%

Post‐Modification of Amino Acids and Peptides for the Rapid Synthesis of C‐Glycoamino Acids and C‐Glycopeptides

et al. 2022

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“…A synthetically useful example of a photooxidation reaction has recently been exemplified by Rao and colleagues [33b] for the synthesis of kynurenine (Kyn) derivatives.…”

Section: Oxidationsmentioning

confidence: 99%

Bioinspired Photocatalyzed Organic Synthetic Transformations. The Use of Natural Pigments and Vitamins in Photocatalysis

2022

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Due to the necessity for more environmentally benign processes in synthetic organic chemistry, and in particular in photocatalysis, a recourse to photocatalysts that are also found in nature and mimic natural processes to accomplish organic transformations is very appealing. Synthetic useful reactions such as oxidations, reductions, carbon-oxygen, carbon-carbon and carbon-sulfur bond formation reactions, and E-to-Z geo-metrical isomerization reactions photocatalyzed by biological natural pigments, vitamins, cofactors, and compounds with antiviral activity will be discussed in this account. Interestingly, due to the remarkable redox properties and triplet energies of some of these catalysts that are found in nature, both electron transfer (ET)-and energy transfer (EnT)-driven photocatalytic processes can be accomplished.

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“…For instance, the cercosporin-photocatalyzed sp 3 (C-H) activation reaction can be used to synthesize pyrrolo[3,4-c]quinolones, which are the backbone structures of various bioactive compounds, such as “A Disintegrin and Metalloproteinase with Thrombospondin Motif” (ADAMTS) inhibitors ( Li et al, 2019 ). The cercosporin-photocatalyzed oxidation reaction can be also employed to synthesize different kynurenine derivatives and the relevant peptides, which present the neuroprotective bioactivity ( Yuan et al, 2022 ). The great pharmacological value of cercosporin and its derivatives has stimulated their isolation from diverse microorganisms.…”

Section: Microbial Perylenequinones Structural Diversity and Bioactivitymentioning

confidence: 99%

Advances and perspectives on perylenequinone biosynthesis

et al. 2022

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Under illumination, the fungal secondary metabolites, perylenequinones (PQs) react with molecular oxygen to generate reactive oxygen species (ROS), which, in excess can damage cellular macromolecules and trigger apoptosis. Based on this property, PQs have been widely used as photosensitizers and applied in pharmaceuticals, which has stimulated research into the discovery of new PQs and the elucidation of their biosynthetic pathways. The PQs-associated literature covering from April 1967 to September 2022 is reviewed in three sections: (1) the sources, structural diversity, and biological activities of microbial PQs; (2) elucidation of PQ biosynthetic pathways, associated genes, and mechanisms of regulation; and (3) advances in pathway engineering and future potential strategies to modify cellular metabolism and improve PQ production.

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Natural product cercosporin as a bioinspired photocatalyst for the synthesis of peptides containing kynurenine via an energy transfer mechanism

Abstract: A cercosporin-catalyzed photo-mediated oxidation for the rapid and efficient synthesis of kynurenine (Kyn) derivatives as well as Kyn-contained peptides under mild conditions was developed, exhibiting great functional group tolerance and...

Cited by 8 publications

References 75 publications

Post‐Modification of Amino Acids and Peptides for the Rapid Synthesis of C‐Glycoamino Acids and C‐Glycopeptides

Post‐Modification of Amino Acids and Peptides for the Rapid Synthesis of C‐Glycoamino Acids and C‐Glycopeptides

Bioinspired Photocatalyzed Organic Synthetic Transformations. The Use of Natural Pigments and Vitamins in Photocatalysis

Advances and perspectives on perylenequinone biosynthesis

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