Structure of a new class of C-nucleoside antibiotic, showdomycin

Nakagawa, Yuzo; Kanō, Hideo; Tsukuda, Y.; Koyama, H.

doi:10.1016/s0040-4039(01)89700-8

Cited by 62 publications

(18 citation statements)

References 4 publications

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“…Showdomycin (SDM) was isolated from Streptomyces showdoensis ATCC 15227 ( S. showdoensis , likewise, other strains were abbreviated in this paper) in 1964 and was synthesized chemically in 1970 [ 13 – 15 ]. The structure of SDM is shown as 3-β- d -ribofuranosylmaleimide, which possesses a unique maleimide-type ring.…”

Section: Biosynthesis Of the Yein-like Type C -Nucleoside Antibioticsmentioning

confidence: 99%

Biosynthesis of C-nucleoside antibiotics in actinobacteria: recent advances and future developments

et al. 2022

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Epidemic diseases and antibiotic resistance are urgent threats to global health, and human is confronted with an unprecedented dilemma to conquer them by expediting development of new natural product related drugs. C-nucleoside antibiotics, a remarkable group of microbial natural products with diverse biological activities, feature a heterocycle base linked with a ribosyl moiety via an unusual C-glycosidic bond, and have played significant roles in healthcare and for plant protection. Elucidating how nature biosynthesizes such a group of antibiotics has provided the basis for engineered biosynthesis as well as targeted genome mining of more C-nucleoside antibiotics towards improved properties. In this review, we mainly summarize the recent advances on the biosynthesis of C-nucleoside antibiotics, and we also tentatively discuss the future developments on rationally accessing C-nucleoside diversities in a more efficient and economical way via synthetic biology strategies.

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Section: Biosynthesis Of the Yein-like Type C -Nucleoside Antibioticsmentioning

confidence: 99%

Biosynthesis of C-nucleoside antibiotics in actinobacteria: recent advances and future developments

et al. 2022

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“…The broad spectrum antibiotic showdomycin possesses an unusual Cnucleoside structure and is formulated as 3-P-~-ribofuranosylmaleimide on the basis of chemical evidence and X-ray analysis. 198 Methanolysis of aldgamycin E liberates the a and P-methylaldgarosides (1 39), which not only possess a rare branched chain octose structure but are the first naturally occurring sugars found to incorporate a cyclic ~a r b 0 n a t e . l ~~ Streptozotocin is an interesting antibacterial agent which liberates diazomethane on contact with alkali and its structure ( 140…”

Section: Me Mementioning

confidence: 99%

“…Photocyclisation of N-chloroacetyl-L-tryptophan provides an easy access to tricyclic indoles [e.g. (196)l. In contrast, N-chloroacetyl-0-methyl-L-tyrosine undergoes an unusual photolysis in water in which the aromatic ring is destroyed and the aza-azulene (198) is formed. The product may arise from the intermediate ( 197) by reverse aldolisation, transannular ring closure, and dehydrat i ~n . '…”

Section: Mementioning

confidence: 99%

Chapter 11. Heterocyclic chemistry

Stoodley¹

1967

Annu. Rep. Prog. Chem., Sect. B

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Reviews.-The chemistry of oxazirans,' tetrapyrroles? glycofuranosides: fur an^,^ 1,2-and 1,3-dithiolium ions,' indoxazenes,6 2-0xazolidones,~ and 1,3,4-oxadiazoles* has been reviewed. Further reviews cover quinacridones,' quinodimethane and its analogues,'O deoxy-sugars, ' ' monocyclic sulphurcontaining pyrones, ' the Hilbert-Johnson reaction of 2,4-dialkoxypyrimidines with halogenoses,' isoall~xazines,'~ pheno~azines,'~ and cephalosporins.'6 The benzene oxide-oxepin and related tautomeri~ms'~ and the chemistry of diazepines' have been considered. The value in heterocyclic syntheses of activated carbon-carbon triple bonds," cyanic esters,20 sulphenes,21 sulphur dioxide imides,22 of reactions of enamines with sulphur and carbon d i ~u l p h i d e ~~ and of ketones with sulphur and ammonia,24 and of cycloaddition reactions2' have been discussed. More general reviews have been concerned with the literature of heterocycles,26 their conf~rmational~' and mass spectral be-

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“…was unraveled later. Pseudouridine is the most abundant natural C -nucleoside present in most tRNA and rRNA structures [ 12 ], where it has been shown to stabilize RNA duplex [ 13 , 14 ]. Showdomycin [ 15 ] possesses well known antibiotic and cytotoxic properties, involving inhibition of nucleoside transport into the cell [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides

et al. 2015

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A novel series of C-nucleosides, featuring the presence of a 1,2,3-triazole ring linked to an isoxazolidine system, has been designed as mimetics of the pyrimidine nucleobases. An antiproliferative effect was observed for compounds 17a and 17b: the growth inhibitory effect reaches the 50% in HepG2 and HT-29 cells and increases up to 56% in the SH-SY5Y cell line after 72 h of incubation at a 100 µM concentration.

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Structure of a new class of C-nucleoside antibiotic, showdomycin

Cited by 62 publications

References 4 publications

Biosynthesis of C-nucleoside antibiotics in actinobacteria: recent advances and future developments

Biosynthesis of C-nucleoside antibiotics in actinobacteria: recent advances and future developments

Chapter 11. Heterocyclic chemistry

Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides

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