533-67-5 Usage
Description
2-Deoxy-D-ribose, also known as a deoxypentose, is a reducing sugar that plays a crucial role in various biological processes. It is formed as a degradation product during the metabolism of thymidine by thymidine phosphorylase. This sugar has a significant impact on cellular functions and is involved in the synthesis of deoxyribonucleic acid (DNA). It is also found as a metabolite in humans, Saccharomyces cerevisiae, and mice.
Uses
Used in Pharmaceutical Applications:
2-Deoxy-D-ribose is used as a precursor to deoxyribonucleic acid (DNA), which is essential for the storage and transmission of genetic information in living organisms. It is also employed in inducing apoptosis by inhibiting the synthesis and increasing the efflux of glutathione, a tripeptide acting as a coenzyme and antioxidant in cells.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Deoxy-D-ribose is used for the synthesis of optically active dipyrrolyl alkanols from pyrroles on the surface of montmorillonite KSF clay. This application highlights its versatility in creating complex organic compounds.
Used in Medical Research:
2-Deoxy-D-ribose (10 μM) has been shown to induce tubulogenesis and migration of bovine aortic endothelial (BAE) cells, which can be significant in understanding and treating various vascular-related conditions.
Used in Wound Healing Applications:
Topical administration of 2-deoxy-D-ribose increases blood vessel formation and accelerates wound healing in a rat full-thickness cutaneous wound model. This application demonstrates its potential in the development of wound care products and therapies.
Chemical Properties:
2-Deoxy-D-ribose is a white powder with reducing sugar properties. It is a deoxypentose in which the hydroxy group at position C-2 is replaced by hydrogen, making it functionally related to D-ribose.
Purification Methods
Dissolve 2-deoxy--D-ribose in a little H2O, evaporate to a syrup (in a vacuum), and seed to crystallise. Triturate the crystals with a little EtOAc containing 5% MeOH, decant and dry in vacuum over P2O5. It is best purified via the anilide which separates from a mixture of the ribose (100-125g) in MeOH (100mL) and redistilled aniline (40mL) in a few minutes. After standing for 20hours at room temperature, it is cooled to 0o, filtered, washed with 50% aqueous MeOH and Et2O followed by recrystallisation from ethylene glycol monomethyl ether. The anilide has m 172-173o, [ ] D 25 +46o (equilibrium in pyridine). The anilide (5g), benzaldehyde (5mL) and benzoic acid (0.5g) in H2O (150mL) are shaken mechanically for 2024hours. The aqueous phase is extracted with Et2O (3x), decolourised with a little charcoal and evaporated in a vacuum to a syrup. This is dried over P2O5 in high vacuum. The syrupy sugar weighs 3.1g and crystallises in a few days, but more rapidly on seeding. Triturate it with a little EtOAc containing 5% MeOH, decant and dry it over P2O5. At this stage it has m 78-82o, [ ] D 25 -57o (c 1, H2O final). This is a mixture of and anomers. Pure -anomer is obtained by recrystallisation from EtOAc The -anomer when recrystallised from EtOAc and isoPrOH has m 96-98o, [ ] D 25 -55o (c 0.5, H2O final). [Sowden Biochemical Preparations 5 75 1957.] The mutarotation is as follows: [] D 20.5 +96.3o(0minutes), -76o(33minutes), -56o (24hours) (c 5.8 MeOH). It is moderately hygroscopic and should be kept in a well stoppered bottle. It also crystallises from diethyl ether. [Deriaz et al. J Chem Soc 1879 1949, Beilstein 1 IV 4181, Hauske & Rapoport J Org Chem 4 4 2472 1979.]
Check Digit Verification of cas no
The CAS Registry Mumber 533-67-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 3 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 533-67:
(5*5)+(4*3)+(3*3)+(2*6)+(1*7)=65
65 % 10 = 5
So 533-67-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O4/c6-2-4-3(7)1-5(8)9-4/h3-8H,1-2H2/t3-,4+,5-/m0/s1
533-67-5Relevant articles and documents
Wong,M.Y.,Gray,G.R.
, p. 3548 (1978)
Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles
Steer, Andrew M.,Bia, Nicolas,Smith, David K.,Clarke, Paul A.
supporting information, p. 10362 - 10365 (2017/09/25)
Understanding the prebiotic genesis of 2-deoxy-d-ribose, which forms the backbone of DNA, is of crucial importance to unravelling the origins of life, yet remains open to debate. Here we demonstrate that 20 mol% of proteinogenic amino esters promote the selective formation of 2-deoxy-d-ribose over 2-deoxy-d-threopentose in combined yields of ≥4%. We also demonstrate the first aldol reaction promoted by prebiotically-relevant proteinogenic amino nitriles (20 mol%) for the enantioselective synthesis of d-glyceraldehyde with 6% ee, and its subsequent conversion into 2-deoxy-d-ribose in yields of ≥ 5%. Finally, we explore the combination of these two steps in a one-pot process using 20 mol% of an amino ester or amino nitrile promoter. It is hence demonstrated that three interstellar starting materials, when mixed together with an appropriate promoter, can directly lead to the formation of a mixture of higher carbohydrates, including 2-deoxy-d-ribose.
Biosynthesis of anti-HCV compounds using thermophilic microorganisms
Rivero, Cintia W.,De Benedetti, Eliana C.,Sambeth, Jorge E.,Lozano, Mario E.,Trelles, Jorge A.
, p. 6059 - 6062 (2012/10/29)
This work describes the application of thermophilic microorganisms for obtaining 6-halogenated purine nucleosides. Biosynthesis of 6-chloropurine- 2′-deoxyriboside and 6-chloropurine riboside was achieved by Geobacillus stearothermophilus CECT 43 with a conversion of 90% and 68%, respectively. Furthermore, the selected microorganism was satisfactorily stabilized by immobilization in an agarose matrix. This biocatalyst can be reused at least 70 times without significant loss of activity, obtaining 379 mg/L of 6-chloropurine-2′-deoxyriboside. The obtained compounds can be used as antiviral agents.
PROCESS FOR PRODUCING 2-DEOXYALDOSE COMPOUND
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Page/Page column 11, (2008/06/13)
An object of the present invention is to provide a method for preparing 2-deoxyaldoses on industrial scale in which the yield or the volumetric efficiency is excellent and the operation is simple, as compared to the conventionally known preparation method.A compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by the catalytic hydrogenation method using a metal such as palladium or the like, or a compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by using a hydride reducing agent in a solvent of not more than 30 weight times the amount of the above compound, for synthesizing 2-keto-3-deoxyaldonic acid. The 2-keto-deoxyaldonic acid was decarboxylated to obtain 2-deoxyaldoses.The method of the present invention is economical and efficiently excellent.
