24259-59-4

Basic information

• Product Name: Ribose
• Synonyms: (2S,3S,4S)-2,3,4,5-Tetrahydroxypentanal;L-Ribose ,98%;L-(+)-Ribos;l-[1-13C]ribose;l-[UL-13C5]ribose;aldehydo-L-ribose;L-(+)-RIBOSE;L-RIBOSE
• CAS NO: 24259-59-4
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• EINECS: 246-110-4
• Product Categories: Monosaccharides;MonosaccharideSpecialty Synthesis;CARBOHYDRATE;Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Nucleosides, Nucleotides & Related Reagents;Ribose;Riboses and 2'-Deoxyriboses;Sugars;Carbohydrates & Derivatives;Carbohydrate Synthesis;Carbohydrates;Carbohydrates A to;Carbohydrates P-ZBiochemicals and Reagents
• Mol File: 24259-59-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 81-82 °C(lit.)
• Boiling Point: 191.65°C (rough estimate)
• Flash Point: 219.2 °C
• Appearance: white crystals or powder
• Density: 1.1897 (rough estimate)
• Vapor Pressure: 3.6E-07mmHg at 25°C
• Refractive Index: 20 ° (C=1, H2O)
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 12.22(at 25℃)
• Water Solubility: Soluble in water (100 mg/ml).
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1723084
• CAS DataBase Reference: Ribose(CAS DataBase Reference)
• NIST Chemistry Reference: Ribose(24259-59-4)
• EPA Substance Registry System: Ribose(24259-59-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-37-36-36/38
• Safety Statements: 24/25-36-26-37/39
• WGK Germany: 3
• RTECS: 246-110-4
• F: 3-10
• Hazardous Substances Data: 24259-59-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical and Biotechnology Industry:
Ribose is used as a key component in the synthesis of RNA and DNA for various applications in the pharmaceutical and biotechnology industries. It plays a vital role in the development of drugs targeting genetic disorders and the study of genetic mechanisms.
2. Used in Organic Synthesis:
L-[1-13C]ribose is a compound used in organic synthesis, which is essential for the development of new chemical compounds and materials with specific properties and applications.
3. Used in Research and Diagnostics:
Ribose is utilized in research and diagnostics, particularly in the study of RNA and DNA structures, functions, and interactions. It is also used in the development of diagnostic tools and techniques for genetic and molecular biology research.
4. Used in Nutritional Supplements:
Ribose is used as an ingredient in nutritional supplements, particularly for athletes and individuals recovering from intense physical activity. It aids in the production of adenosine triphosphate (ATP), which is essential for energy production in cells.
5. Used in Food Industry:
Ribose is employed in the food industry as a natural flavor enhancer and sweetener due to its sugar-like properties.
6. Produced by Microorganism Fermentation:
Ribose is produced through the fermentation of glucose by microorganisms in a fermentation culture medium without the addition of calcium carbonate. This method is used to obtain ribose for various industrial applications.

InChI:InChI=1/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5+/m0/s1

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 152202-52-3 L-arabinal 
• 5328-37-0 L-arabinose 
• 50-00-0 formaldehyd 
• 608-66-2 D-galactitol 
• 7732-18-5 water 
• 96-26-4 dihydroxyacetone 
• 141-46-8 Glycolaldehyde 
• 56-82-6 Glyceraldehyde 
• 1949-78-6 L-lyxose 
• 1114-34-7 D-lyxose 
• 2595-05-3 Diacetone D-glucose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 

Downstream Products

• 50-69-1 rac-Ribose 
• 488-81-3 Adonitol 
• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 206269-25-2 methyl 2,3,5-tri-O-acetyl-β-L-ribofuranoside 
• 13501-95-6 Acetic acid 2,3-diacetoxy-1-((S)-acetoxy-cyano-methyl)-propyl ester 
• 525596-18-3 4-N-benzoyl-1-(2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl)cytosine 
• 525596-17-2 1-(2-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl)uracil 
• 525596-16-1 4-N-benzoyl-1-[5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl]cytosine 
• 525596-15-0 1-(5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl)uracil 

Relevant articles and documents

A new oleanane-type triterpenoidal saponin from Pulsatilla chinensis

A new oleanane-type triterpenoidal saponin, 3-O-β-d-glucopyranosyl- hederagenin 23-O-α-d-ribofuranoside (1), was isolated from the roots of Pulsatilla chinensis, and its structure was established on the basis of the spectral data. Compounds 2, 7 and 8 showed moderate cytotoxic activity by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazoliumbromide assay. 2013

Directed evolution toward improved production of L-ribose from ribitol

Improvement of the one-step production of L-ribose from ribitol using a recombinant Escherichia coli is described. The gene encoding the enzyme mannitol-1-dehydrogenase (MDH) from Apium graveolens has previously been codon-optimized, cloned into the constitutive pZuc10 vector, and expressed in E. coli. This MDH catalyzes the NADdependent conversion of mannitol to D-mannose and has the ability to convert several polyols to their L-sugar counterparts, including ribitol to L-ribose. Here, three rounds of directed evolution using libraries generated through errorprone PCR and screened using a dinitrosalicylate reagent. Mutants were selected for improved conversion of L-ribose, and the best mutant was isolated by combining two round 2 mutations. Libraries were also selected for thermal stability and screened at increasingly higher temperatures with each round of mutagenesis. An overall 19.2-fold improvement was observed with a final conversion of 46.6 ± 1.7% and a productivity of 3.88 ± 0.14 gL-1d-1 in 50 mL shaken flasks at 34 °C. Further characterization of the mutants suggests that increased enzyme thermal stability and expression are responsible for the increase in L-ribose production. The mutant E. coli production strain isolated represents an improved system for largescale production of L-ribose.

NAD(P)H oxidase v from Lactobacillus plantarum (NoxV) displays enhanced operational stability even in absence of reducing agents

Active pharmaceutical ingredients (APIs) such as l-sugars and keto acids are favorably accessed through selective oxidation of sugar alcohols and amino acids, respectively, catalyzed by NAD(P)-dependent dehydrogenases. Cofactor regeneration from NAD(P)H conveniently is achieved via water-forming NAD(P)H oxidases (nox2), which only need molecular oxygen as co-substrate. Turnover-dependent overoxidation of the conserved cysteine residue in the active site of water-forming NADH oxidases is the presumed cause of the limited nox2 stability. We present a novel NAD(P)H oxidase, NoxV from Lactobacillus plantarum, with specific activity of 167 U/mg and apparent kinetic constants at air saturation and 25 °C of kcat,app = 212 s-1 and KM,app = 50.2 μM in the broad pH optimum from 5.5 to 8.0. The enzyme features a higher stability than other NAD(P)H oxidases against overoxidation, as is evidenced by a higher total turnover number, in the presence (168,000) and, most importantly, also in the absence (128,000) of exogenously added reducing agents. While the native enzyme shows exclusively activity on NADH, we engineered the substrate binding pocket to generate variants, G178K,R and L179K,R,H that accommodate and oxidize both NADH and NADPH as substrates.

Catalytic consequences of borate complexation and pH on the epimerization of l-arabinose to l-ribose in water catalyzed by Sn-Beta zeolite with borate salts

Sn-Beta zeolite with sodium tetraborate cooperatively catalyzes the epimerization of aldoses via an intramolecular 1,2 carbon-shift mechanism. l-Arabinose is one of the seven common sugars and its epimer, l-ribose, is a valuable rare sugar with applications in antiviral and anticancer agents. Here, a full factorial experimental design is performed to demonstrate the catalytic consequences of varying key reaction parameters such as pH, borate to sugar ratio, and reaction time. Reactivity data revealed that isomerization is favored under acidic pH conditions (pH 7.8). Using a 5 wt% arabinose feed and 100:1 sugar-metal ratios at 343 K, conversions ranging from 20% to 30% were obtained with selectivities of 75%, 84%, and 91% for boron-sugar ratios of 0.2:1, 0.5:1, and 1:1, respectively. The predominance of epimerization over isomerization products with substoichiometric borate suggests that one borate can influence the reactivity of several sugar molecules and may influence the Sn active site directly. Reaction data obtained under differential conditions revealed that the epimerization reaction follows first order kinetics over a wide temperature range with an apparent activation energy of 98 kJ/mol and pre-exponential factor of 1.9 × 1014 L mol Sn-1 s-1.

A heterogeneous Pd-Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars

A critical step in the synthesis of the rare sugars, l-lyxose and l-ribose, from the corresponding d-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5:1 atomic ratio of Pd:Bi. The overall yields of the five-step procedure to l-ribose and l-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.

L-Ribose: An easily prepared rare sugar

A method to synthesize L-ribose was described by molybdate-catalyzed epimerization of the readily available L-arabinose. The synthesis is one-step and except for a catalytic amount of molybdic acid do not require any expensive reagents, while the solvents used are water and a small amount of methanol. The process can be carried out in 2-3 days. Although the yield of L-ribose is only 20%, being in equilibrium with arabinose, most of the unreacted arabinose is recoverable and can be used again.

Separation process

The invention relates to a process of recovering arabinose and optionally other monosaccharides from vegetable fiber rich in heteropolymeric arabinose, such as gum arabic. Said other monosaccharides are typically selected from galactose and rhamnose. The process of the invention comprises controlled hydrolysis of the arabinose-rich vegetable fiber and fractionation of the hydrolysis product to obtain a fraction enriched in arabinose and optionally other product fractions followed by crystallization of arabinose. The invention also relates to a novel method of crystallizing arabinose from biomass-derived material. Furthermore, the invention relates to novel crystalline L-arabinose.

Process for preparation of L-ribose using 1,4-lactone

The present invention relates to a process for effectively preparing L-ribose, which is recognized as being highly important in relation to the development of new antiviral medicines, from 1,4-lactone compound.

Synthesis of racemic ribose from D-glucose

Racemic ribose is a valuable starting material for investigations of the origins of biomolecular homochirality. It can be synthesized in seven steps starting from D-glucose.

Intermediates for preparing optically active carboxylic acids

A process is described for preparing optically active alpha-arylalkanoic acids consisting of rearranging an optically active ketal of formula STR1 in which the substituents have the meaning given in the description of the invention.