16755-07-0

Basic information

• Product Name: 3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE
• Synonyms: SHOWDOMYCIN;2-beta-d-ribofuranosyl-maleimid;2-beta-d-ribofuranosylmaleimide;3-beta-d-ribofuranosyl-1h-pyrrole-2,5-dione;3-beta-d-ribofuranosyl-1h-pyrrole-5-dione;d-(+)-showdomycin;d-showdomycin;3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE
• CAS NO: 16755-07-0
• Molecular Formula: C9H11NO6
• Molecular Weight: 229.19
• Mol File: 16755-07-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 153-154°
• Boiling Point: 371.08°C (rough estimate)
• Flash Point: 293.9°C
• Appearance: /
• Density: 1.4278 (rough estimate)
• Vapor Pressure: 5.47E-15mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• PKA: 8.08±0.40(Predicted)
• CAS DataBase Reference: 3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE(16755-07-0)
• EPA Substance Registry System: 3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE(16755-07-0)

Safety Data

• Hazardous Substances Data: 16755-07-0(Hazardous Substances Data)

Usage

Description

3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE, also known as 2-β-D-Ribofuranosyl-maleimide, is a chemical compound with a unique structure that features a ribofuranosyl group attached to a pyrrole-2,5-dione ring. 3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE has been found to possess various biological activities, making it a valuable compound for research and potential applications in different industries.

Uses

Used in Pharmaceutical Industry:
3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE is used as an active pharmaceutical ingredient for its antibacterial properties. It demonstrates the ability to inhibit the growth of various bacteria, making it a promising candidate for the development of new antibiotics to combat bacterial infections.
Used in Chemical Research:
In the field of chemical research, 3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE serves as a valuable chemical reagent due to its unique structure and properties. Researchers can utilize this compound in the synthesis of other complex molecules or to study its interactions with various biological targets.
Used in Material Science:
The unique structure of 3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE may also find applications in material science, where it could be used to develop new materials with specific properties, such as improved stability or enhanced biological activity.

InChI:InChI=1/C9H11NO6/c11-2-4-6(13)7(14)8(16-4)3-1-5(12)10-9(3)15/h1,4,6-8,11,13-14H,2H2,(H,10,12,15)

Upstream product

• 54503-64-9 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose 
• 66149-72-2 3-[O⁵-(tert-butyl-dimethyl-silanyl)-O²,O³-isopropylidene-β-D-ribofuranosyl]-pyrrole-2,5-dione 
• 75467-21-9 methyl 2-(2',3'-di-O-methoxymethyl-5'-O-tert-butyldimethylsilyl-β-D,L-arabinofuranosyl) glyoxylate 
• 75467-16-2 methyl 2-(2',3'-di-O-methoxymethyl-5'-O-tert-butyldimethylsilyl-β-D,L-arabinofuranosyl) glycolate 
• 75467-14-0 methyl 2-(2',3'-di-O-methoxymethyl-β-D,L-arabinofuranosyl) glycolate 
• 75467-23-1 2-(2',3'-di-O-methoxymethyl-5'-O-tert-butyldimethylsilyl-β-D,L-arabinofuranosyl)maleimide 
• 66268-91-5 [(3aS,4S,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-oxo-acetic acid methyl ester 
• 75467-31-1 [(3aR,4R,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-hydroxy-acetic acid methyl ester 
• 75467-29-7 Hydroxy-((3aR,4R,6S,6aS)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester 
• 78442-65-6 2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester 
• 78442-66-7 3-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrolidine-2,5-dione 
• 78442-64-5 (3aS,4S,6S,6aS)-6-(2-Cyano-1-methoxycarbonyl-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 
• 78442-63-4 (1S,2S,6S,7S,8S)-8-Cyanomethyl-4,4-dimethyl-9-oxo-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid methyl ester 
• 78442-61-2 (1S,2S,6R,7R)-9-[1-Methoxycarbonyl-meth-(E)-ylidene]-4,4-dimethyl-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid methyl ester 

Downstream Products

• 69100-09-0 3-(5-iodo-β-D-5-deoxy-ribofuranosyl)-pyrrole-2,5-dione 

Relevant articles and documents

Showdomycin as a versatile chemical tool for the detection of pathogenesis-associated enzymes in bacteria

Showdomycin is a potent nucleoside antibiotic that displays a high structural similarity to uridine and pseudouridine. No detailed target analysis of this very unusual electrophilic natural product has been carried out so far. To unravel its biological function, we synthesized a showdomycin probe that can be appended with a fluorophor or a biotin marker via click chemistry and identified diverse enzymes which were important for either the viability or virulence of pathogenic bacteria. Our results indicate that the antibiotic effect of showdomycin against Staphylococcus aureus may be due to the inhibition of various essential enzymes, especially MurA1 and MurA2, which are required for cell wall biosynthesis. Although real-time polymerase chain reaction revealed that the MurA2 gene was expressed equally in four S. aureus strains, our probe studies showed that MurA2 was activated in only one multiresistant S. aureus strain, and only this strain was resistant to elevated concentrations of the MurA inhibitor fosfomycin, suggesting its potential role as an antibiotic bypass mechanism in the case of MurA1 inhibition. Moreover, we utilized this tool to compare enzyme profiles of different pathogenic strains, which provided unique insights in regulatory differences as well as strain-specific signatures.

Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis

Showdomycin is a C-nucleoside bearing an electrophilic maleimide base. Herein, the biosynthetic pathway of showdomycin is presented. The initial stages of the pathway involve non-ribosomal peptide synthetase (NRPS) mediated assembly of a 2-amino-1H-pyrrole-5-carboxylic acid intermediate. This intermediate is prone to air oxidation whereupon it undergoes oxidative decarboxylation to yield an imine of maleimide, which in turn yields the maleimide upon acidification. It is also shown that this pyrrole intermediate serves as the substrate for the C-glycosidase SdmA in the pathway. After coupling with ribose 5-phosphate, the resulting C-nucleoside undergoes a similar sequence of oxidation, decarboxylation and deamination to afford showdomcyin after exposure to air. These results suggest that showdomycin could be an artifact due to aerobic isolation; however, the autoxidation may also serve to convert an otherwise inert product of the biosynthetic pathway to an electrophilic C-nucleotide thereby endowing showdomycin with its observed bioactivities.

Chirally Selective Synthesis of Sugar Moiety of Nucleosides by Chemicoenzymatic Approach: L- and D-Riboses, Showdomycin, and Cordycepin

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Subclass-specific labeling of protein-reactive natural products with customized nucleophilic probes

Natural products represent a rich source of bioactive compounds that constitute a large fraction of approved drugs. Among those are molecules with electrophilic scaffolds, such as Michael acceptors, b-lactams, and epoxides that irreversibly inhibit essent

TOTAL SYNTHESIS OF D-(+)-SHOWDOMYCIN FROM SYN-2,5-DISUBSTITUTED TETRAHYDROFURAN

D-(+)-Showdomycin, first isolated from Streptomyces showdoensis, has been synthesized starting from syn-2,5-disubstituted dihydrofuran 3.The key conversion was the functionalization of 2-thiophenylfuranyl group in 13 into maleic acid moiety in 12.