533-67-5

Basic information

• Product Name: 2-Deoxy-D-ribose
• Synonyms: D-.alpha.-Ribodesose;Deoxyribose;D-Ribose, 2-deoxy-;Ribose, 2-deoxy-, D-;2-DEOXYRIBOSE;2-DESOXY-D-RIBOSE;2'-DEOXY-D-RIBOSE;2-DEOXY-D-RIBOSE
• CAS NO: 533-67-5
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.13
• EINECS: 208-573-0
• Product Categories: Pharmaceutical Raw Materials;FINE Chemical & INTERMEDIATES;13C & 2H Sugars;Riboses and 2'-Deoxyriboses;Biochemistry;Deoxysugars;Nucleosides, Nucleotides & Related Reagents;Ribose;Sugars;Dextrins、Sugar & Carbohydrates;aldehydes;Carbohydrates & Derivatives;nucleoside
• Mol File: 533-67-5.mol

Chemical Properties

• Melting Point: 89-90 °C(lit.)
• Boiling Point: 167.23°C (rough estimate)
• Flash Point: 197.601 °C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.0590 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -56 ° (C=1, H2O)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• PKA: 12.61(at 25℃)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• Merck: 14,2908
• BRN: 1721978
• CAS DataBase Reference: 2-Deoxy-D-ribose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-D-ribose(533-67-5)
• EPA Substance Registry System: 2-Deoxy-D-ribose(533-67-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-37/39-36-26
• WGK Germany: 3
• RTECS: SB7230000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 533-67-5(Hazardous Substances Data)

Usage

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.]

InChI:InChI=1/C5H10O4/c6-2-4-3(7)1-5(8)9-4/h3-8H,1-2H2/t3-,4+,5-/m0/s1

Synthetic route

sodium 3-deoxy-D-mannonate (93857-40-0) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water pH=5; Stage #2: With sodium hypochlorite; acetic acid In water at 40 - 45℃; for 2h; pH=5 - 6;	95%
Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water pH=5; Stage #2: With hydrogenchloride; sodium hypochlorite; acetaldehyde In water at 40 - 45℃; for 2h; pH=5 - 6;	94%
Stage #1: sodium 3-deoxy-D-mannonate With hydrogenchloride In water pH=5; Stage #2: With hydrogenchloride; sodium hypochlorite; formaldehyd In water at 40 - 45℃; for 2h; pH=5 - 6;	94%

D-arabino-3-deoxy-hexonic acid (1518-59-8) + 3-deoxy-D-arabino-hexono-1,4-lactone (50480-80-3) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Stage #1: D-arabino-3-deoxy-hexonic acid; 3-deoxy-D-arabino-hexono-1,4-lactone With sodium carbonate In water at 20℃; pH=8.8; Stage #2: With sodium hypochlorite In water for 1 - 4h; pH=4.5 - 5.0; Stage #3: With sodium sulfite In water	93%

(S)-2-Amino-6-{3-[(E)-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-methyl-acryloyl]-ureido}-hexanoic acid (87616-31-7) → 2-Deoxy-D-ribose (533-67-5) + (2S)-amino-6-(1-thyminyl)hexanoic acid (76945-38-5)

Conditions	Yield
With pH 10.5 In water at 90℃;	A n/a B 90%

4,5,6-trihydroxy-2-oxohexanoic acid (17510-99-5) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With cerium(IV) sulphate; sulfuric acid; palladium 10% on activated carbon In water at 37℃;	51%

potassium 2-dehydro-3-deoxy-D-gluconate → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Stage #1: potassium 2-dehydro-3-deoxy-D-gluconate With sulfuric acid; hydrogen; palladium 10% on activated carbon In water at 50℃; Stage #2: With calcium carbonate In water Stage #3: With calcium hydroxide; carbon dioxide; dihydrogen peroxide; copper diacetate; iron(II) sulfate more than 3 stages;	47%

6,6-bis-ethanesulfonyl-L-erythro-hex-5-ene-1,2,3-triol → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With ammonium hydroxide

3-deoxy-D-glucose (2490-91-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With sodium periodate; water und anschliessend mit wss.Ammoniak;

D-glucose (50-99-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With calcium hydroxide; water at 120℃; und Behandeln der vom Calciumhydroxid befreiten, mit Eisen(III)-sulfat und Bariumacetat versetzen Loesung des Reaktionsprodukts mit wss.Wasserstoffperoxid;

3-O-methyl-D-glucose (146-72-5, 2922-60-3, 4682-46-6, 5153-62-8, 32166-87-3, 38088-21-0, 62396-68-3, 65725-72-6, 90364-89-9, 126874-17-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With calcium hydroxide; water Erwaermen des Reaktionsprodukts mit Eisen(III)-sulfat,Bariumacetat und wss.Wasserstoffperoxid;

O3-(toluene-4-sulfonyl)-D-glucose (50705-39-0) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With calcium hydroxide; water

D-erythro-[2]pentulose-(2-nitro-phenylhydrazone) (91338-48-6, 91338-49-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With water; nickel Hydrogenation.Behandlung des Reaktionsprodukts mit wss.Essigsaeure und Natriumnitrit;

2-deoxy-α-D-erythro-pentofuranose (36792-87-7) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With diclazuril In water-d2 at 43.3℃; Equilibrium constant; Rate constant;

[R-(R*,R*)]-5-Hexene-1,2,3-triol (89534-51-0) → D-threo-2-deoxy-pentose (5284-18-4) + 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With ozone In methanol at -78℃; for 0.75h; Title compound not separated from byproducts;

2-deoxy-D-ribose (36792-88-8) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With diclazuril In water-d2 at 43.3℃; Equilibrium constant; Rate constant;

2'-Deoxyguanosine (961-07-9) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With water; potassium bromide; dinitrogen monoxide Mechanism; Irradiation; G value of product; other reagent - N2/O2 instead of N2O;

4,4-dimethyl-3-<(trimethylsilyl)oxy>pentan-2-one (88264-38-4) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → D-threo-2-deoxy-pentose (5284-18-4) + 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propionaldehyde (74310-52-4) → D-threo-2-deoxy-pentose (5284-18-4) + 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With acetic acid for 12h; Ambient temperature; Title compound not separated from byproducts;

((4R,5S)-5-[1,3]Dioxolan-2-ylmethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With acid

(S)-5-Guanidino-2-{3-[(E)-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-methyl-acryloyl]-ureido}-pentanoic acid (87616-32-8) → 2-Deoxy-D-ribose (533-67-5) + (S)-5-Guanidino-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentanoic acid (87616-33-9)

Conditions	Yield
In water Heating;

1-(β-D-erythro-3-deoxy-pentofuranosyl)-4-methoxy-1H-pyrimidin-2-one (37117-02-5) → 2-Deoxy-D-ribose (533-67-5) + O2-methyluracil (25902-86-7)

Conditions	Yield
With hydrogenchloride In water at 32℃; Rate constant; pH dependence;

1-(2-deoxy-β-D-erythro-pentofuranosyl)-2-methoxy-5-methyl-4(1H)-pyrimidinone (37085-48-6) → 2-Deoxy-D-ribose (533-67-5) + 2-Methoxy-5-methyl-1H-pyrimidin-4-one (25902-91-4)

Conditions	Yield
With hydrogenchloride In water at 32℃; Rate constant; pH dependence;

2'-deoxy-D-adenosine (958-09-8) → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With water; potassium bromide; dinitrogen monoxide Mechanism; Irradiation; G value of product; other reagent - N2/O2 instead of N2O;

(3R)-3,4-dihydro-2H-pyran-3r,4c-diol → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With sulfuric acid

deoxyribonucleic acid substances from the roe of fish → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
Hydrolysis.durch enzymatische Hydrolyse und anschliessende Hydrolyse mit Hilfe eines sauren und eines schwach basischen Ionenaustauschers;

D-erythro-3,4,5-triacetoxy-1-nitro-pent-1-ene → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With ethanol; palladium Hydrogenation.und Behandlung des Reaktionsprodukts mit wss.-aethanol.Natronlauge und anschliessend mit wss.Schwefelsaeure;

methyl- → 2-Deoxy-D-ribose (533-67-5)

Conditions	Yield
With methanol; sodium methylate Erhitzen des Reaktionsprodukts mit wss.Essigsaeure;

methanol (67-56-1) + 2-Deoxy-D-ribose (533-67-5) → 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5, 51255-18-6, 60134-26-1, 89577-26-4, 96038-80-1, 96039-31-5, 144301-84-8, 144301-85-9)

Conditions	Yield
With hydrogenchloride	100%
With hydrogenchloride	100%
With hydrogenchloride at 0 - 20℃;	98%

methanol (67-56-1) + 2-Deoxy-D-ribose (533-67-5) → 1-O-methyl-α-2-deoxy-D-erythro-pentofuranose (51255-17-5)

Conditions	Yield
With hydrogenchloride at 25℃; for 0.666667h;	99.6%

2-Deoxy-D-ribose (533-67-5) + (2,5-dichlorophenyl)hydrazine (305-15-7) → 2-deoxyribose (2,5-dichlorophenyl)hydrazone

Conditions	Yield
In methanol Heating;	99%

2-Deoxy-D-ribose (533-67-5) + 1-Aminopiperidine (2213-43-6) → (2R,3S)-5-(piperidin-1-ylimino)pentane-1,2,3-triol

Conditions	Yield
In methanol for 1h; Reflux;	98%

2-Deoxy-D-ribose (533-67-5) + 1,1-Diphenylhydrazine (530-50-7) → (R,S,E)-5-[(N,N-diphenyl)hydrazono]pentane-1,2,3-triol

Conditions	Yield
With acetic acid In methanol at 20℃; for 1h;	98%

2-Deoxy-D-ribose (533-67-5) + acetic anhydride (108-24-7) → (3,4,5-triacetoxy)pentanenitrile (49560-18-1)

Conditions	Yield
With ammonium hydroxide; N-Bromosuccinimide at 0℃; for 0.25h;	97%

1.3-propanedithiol (109-80-8) + 2-Deoxy-D-ribose (533-67-5) → 2-deoxy-D-erythro-pentose cyclic 1,3-propanediyl mercaptal (50907-65-8)

Conditions	Yield
With hydrogenchloride; water In chloroform at 20℃;	90%
With hydrogenchloride In chloroform; water at 0 - 20℃; Inert atmosphere;	75%

2-Deoxy-D-ribose (533-67-5) → 2-deoxy-D-ribonolactone (34371-14-7)

Conditions	Yield
With bromine In water at 25℃; for 120h;	88%
With bromine In water at 20℃; for 120h;	78%
With bromine; potassium carbonate In water at 20℃; for 8h;	70%
With bromine In water at 20℃; for 120h; Sealed tube;
With bromine In water at 20℃; for 120h; Sealed tube;

2-Deoxy-D-ribose (533-67-5) + N-aminopyrrolidine (16596-41-1) → (2R,3S)-5-(pyrrolidin-1-ylimino)pentane-1,2,3-triol

Conditions	Yield
In methanol for 1.5h; Reflux;	88%

methanol (67-56-1) + 2-Deoxy-D-ribose (533-67-5) → methyl-2-deoxyribopyranoside (863396-35-4)

Conditions	Yield
With hydrogenchloride	85%

2-Deoxy-D-ribose (533-67-5) + Methyltriphenylphosphonium bromide (1779-49-3) → (2R,3S)-hex-5-ene-1,2,3-triol (79364-36-6)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-Deoxy-D-ribose In tetrahydrofuran at 0 - 40℃; for 24h; Wittig Olefination;	85%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-Deoxy-D-ribose In tetrahydrofuran at 35℃; for 24h; Wittig reaction;	75%

2-Deoxy-D-ribose (533-67-5) + ethanethiol (75-08-1) → 2-deoxy-D-erythro-pentose diethyl dithioacetal (115214-11-4)

Conditions	Yield
With hydrogenchloride at 0℃; for 1h; Inert atmosphere;	83%
With hydrogenchloride at 20℃; for 3h;	71%
With hydrogenchloride
With hydrogenchloride

2-Deoxy-D-ribose (533-67-5) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate (78606-78-7)

Conditions	Yield
benzoic acid In 1,2-dimethoxyethane for 5h; Heating;	82%

2-Deoxy-D-ribose (533-67-5) → lithium 2-deoxy-D-erythro-pentonate (78096-97-6)

Conditions	Yield
With potassium hydroxide; lithium hydroxide; dihydrogen peroxide; magnesium oxide 1.) 2 h, RT, 2.) 18 h, 40 deg C;	80%

2-Deoxy-D-ribose (533-67-5) + dibenzylamine (103-49-1) → (2R,3S)-5-(dibenzylamino)pentane-1,2,3-triol (910658-48-9)

Conditions	Yield
Stage #1: 2-Deoxy-D-ribose; dibenzylamine In dichloromethane for 24h; Stage #2: With sodium tetrahydroborate In dichloromethane at 0 - 20℃; for 3h;	78%

2-Deoxy-D-ribose (533-67-5) + benzyl alcohol (100-51-6) → (3R,4S)-6-Benzyloxy-tetrahydro-pyran-3,4-diol (418760-06-2)

Conditions	Yield
With dimethylsilicon dichloride at 25℃;	76%

2-Deoxy-D-ribose (533-67-5) + tetraallyl tin (7393-43-3) → (2R,3S)-Oct-7-ene-1,2,3,5-tetraol (195196-44-2)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In ethanol; water; toluene at 70℃; for 5h;	75%

2-Deoxy-D-ribose (533-67-5) + 1-azepanylamine (5906-35-4) → (2R,3S)-5-(azepan-1-ylimino)pentane-1,2,3-triol

Conditions	Yield
In methanol for 0.75h; Reflux;	73%

2-Deoxy-D-ribose (533-67-5) → (2R,3S)-5-aminopentane-1,2,3-triol (64869-48-3)

Conditions	Yield
With ammonium hydroxide; ammonium acetate; sodium cyanoborohydride In ethanol Reflux;	73%
With transaminase biocatalyst ATA256; isopropylamine for 48h; Reagent/catalyst; Enzymatic reaction;	69%

2-Deoxy-D-ribose (533-67-5) + 2,2-dimethoxy-propane (77-76-9) → 3,4-O-isopropylidene-2-deoxy-d-ribose (65236-75-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 0℃;	72%

2-Deoxy-D-ribose (533-67-5) + ethane-1,2-dithiol (540-63-6) → 2-Deoxy-D-ribose Ethylene Mercaptal (43179-62-0)

Conditions	Yield
With hydrogenchloride 1.) 5 deg C, 10 min 2.) 1 h, room temp.;	71%
With hydrogenchloride

Upstream product

• 2490-91-7 3-deoxy-D-glucose 
• 50-99-7 D-glucose 
• 146-72-5 3-O-methyl-D-glucose 
• 50705-39-0 O³-(toluene-4-sulfonyl)-D-glucose 
• 91338-48-6 D-erythro-[2]pentulose-(2-nitro-phenylhydrazone) 
• 36792-87-7 2-deoxy-α-D-erythro-pentofuranose 
• 22900-10-3 2-deoxy-β-D-erythro-pentopyranose 
• 36792-85-5 2-deoxy-α-D-erythro-pentopyranose 
• 79364-36-6 (2R,3S)-hex-5-ene-1,2,3-triol 
• 89534-51-0 [R-(R*,R*)]-5-Hexene-1,2,3-triol 
• 36792-88-8 2-deoxy-D-ribose 
• 961-07-9 2'-Deoxyguanosine 
• 88264-38-4 4,4-dimethyl-3-<(trimethylsilyl)oxy>pentan-2-one 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 

Downstream Products

• 7284-15-3 2-deoxy-D-ribonic acid 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 17685-02-8 1,3,5-tri-O-benzoyl-2-deoxy-β-D-ribopyranosa 
• 17685-01-7 tri-O-benzoyl-α-D-erythro-2-deoxy-pentopyranose 
• 43179-62-0 2-Deoxy-D-ribose Ethylene Mercaptal 
• 525-79-1 kinetin 
• 6301-46-8 D-erythro-2-deoxy-pentose-diisopropyldithioacetal 
• 3945-25-3 N-phenyl-α-D-erythro-2-deoxy-pentopyranosylamine 
• 176214-54-3 2-deoxy-D-ribose dibenzyldithioacetal 
• 109285-84-9 toluene-4-sulfonic acid-(D-erythro-2-deoxy-pentitol-1-ylidenehydrazide) 
• 1518-59-8 D-arabino-3-deoxy-hexonic acid 
• 129815-29-8 (E)-(5S,6R)-5,6,7-Trihydroxy-hept-2-enoic acid benzyl ester 
• 36792-87-7 2-deoxy-α-D-erythro-pentofuranose 
• 22900-10-3 2-deoxy-β-D-erythro-pentopyranose 

Relevant articles and documents

Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles

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.

Method for preparing 2-deoxy-D-ribose

The invention provides a method for preparing 2-deoxy-D-ribose, and belongs to the technical field of organic synthesis.The method includes the following steps that A, 3,4-O-diacetyl-D-arabinal is dissolved into organic solvents, lithium bromide or lithium chloride, strong acid cation exchange resin and water are added, and the mixture is reacted to obtain 3,4-O-diacetyl-deoxy-D-ribose; B, the 3,4-O-diacetyl-deoxy-D-ribose is subjected to hydrolysis reaction to obtain the 2-deoxy-D-ribose.According to the method for preparing the 2-deoxy-D-ribose, due to the effect of the lithium bromide, the strong acid cation exchange resin and the water, the yield of the 2-deoxy-D-ribose is increased, postprocessing is simple and convenient, production cost is reduced, and therefore the method can be widely applied to industrial production.

Biosynthesis of anti-HCV compounds using thermophilic microorganisms

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.

The 1H NMR method for the determination of the absolute configuration of 1,2,3-prim,sec,sec-triols

The absolute configuration of 1,2,3-prim,sec,sec-triols can be assigned by comparison of the 1H NMR spectra of the tris-(R)- and the tris-(S)-MPA ester derivatives. An experimental demonstration of this correlation with 24 triols of known absolute configuration and a protocol using two parameters-ΔδRS(H3) and the difference between ΔδRS(H2) and ΔδRS(H3) = |Δ(ΔδRS)|-for its application to the determination of the absolute configuration of other triols are presented.

Novel gluconate dehydratase

A novel gluconate dehydratase derived from Achromobacter xylosoxidans and a gene encoding the gluconate dehydratase are provided. By reacting the gluconate dehydratase or a transformed cell containing the gene with an aldonic acid, the corresponding 2-keto-3-deoxyaldonic acid can be efficiently produced.

PROCESS FOR PRODUCING 2-DEOXYALDOSE COMPOUND

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.

Production of aldoses

An aldose having n-1 carbon atoms is produced from an aldonic acid having n carbon atoms using hypochlorous acid or a hypochlorite in a high yield at low cost with safety, by treating the reaction mixture with a compound having reactivity with the hypochlorous acid or hypochlorite higher than that with the produced aldose.

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.

SUBSTRATE SPECIFICITY AND ENANTIOSELECTIVITY OF PENICILLINACYLASE CATALYZED HYDROLYSIS OF PHENACETYL ESTERS OF SYNTHETICALLY USEFUL CARBINOLS

Penicillinacylase from E. coli, immobilized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23 deg C, of a set of O-phenylacetate esters of primary carbinols.The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework.Minor modifications of this basic structure are not altering the acceptability by the enzyme, but significantly decrease the enantioselectivity of the hydrolysis, as does the use of benzene as solvent and Sepharose-bound enzyme.