3083-77-0

Basic information

• Product Name: Spongouridine
• Synonyms: 1-beta-d-arabinofuranosyl-uraci;1-[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;1-beta-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione;Spongouridine;Uridine;1--D-Arabinofuranosyl-2,4(1H,3H)-pyrimidinedione;NSC 68928;1-(β-D-Arabinopyranosyl)uracil
• CAS NO: 3083-77-0
• Molecular Formula: C₉H₁₂N₂O₆
• Molecular Weight: 244.2
• EINECS: 221-386-9
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 3083-77-0.mol
• Article Data: 42

Chemical Properties

• Melting Point: 220-222°C
• Appearance: White to Off-white/Powder
• Density: 1.674 g/cm³
• Refractive Index: 1.643
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: pK1:9.30 (25°C)
• BRN: 28749
• CAS DataBase Reference: Spongouridine(CAS DataBase Reference)
• NIST Chemistry Reference: Spongouridine(3083-77-0)
• EPA Substance Registry System: Spongouridine(3083-77-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: YQ8818000
• F: 3
• Hazardous Substances Data: 3083-77-0(Hazardous Substances Data)

Usage

Description

1-β-D-Arabinofuranosyluracil (ara-U) is an inactive metabolite of cytarabine . Ara-U is formed when cytarabine undergoes deamination by cytidine deaminase.

Chemical Properties

White to Off-White Solid

Uses

Antiviral agent.1-β-D-Arabinofuranosyluracil is used for the treatment of severe acute respiratory syndrome (SARS).

Definition

ChEBI: A natural product found in Lepisorus contortus.

InChI:InChI=1/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7+,8-/m1/s1

Synthetic route

1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil (14057-18-2) → araU (3083-77-0)

Conditions	Yield
With keratinase from Paecilomyces marquandii for 216h; pH=8; aq. phosphate buffer; Enzymatic reaction;	100%

arabinosyl cytosine (147-94-4) → araU (3083-77-0)

Conditions	Yield
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction;	99%
cytidine deaminase ( EC 3.5.4.5 ) at 37℃; for 48h; pH=6.8 with acetic acid;
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products;

2,2'-Anhydrouridine (3736-77-4) → araU (3083-77-0)

Conditions	Yield
With trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 10h;	95%
With trifluoroacetic acid In N,N-dimethyl-formamide at 80℃;	95%
Stage #1: 2,2'-Anhydrouridine With sodium hydroxide; water at 20℃; for 18 - 20h; Stage #2: With hydrogenchloride; water pH=~ 6.5;	88%

2,2'-Anhydrouridine 3'-carbamate (87186-13-8) → araU (3083-77-0)

Conditions	Yield
With water; triethylamine at 60℃; for 48h;	90%

2,2''-anhydro-1-(3'',5''-di-O-acetyl-β-D-arabinofuranosyl)uracil (28309-53-7) → araU (3083-77-0)

Conditions	Yield
With sodium hydroxide for 4h; Ambient temperature;	68%

1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one (847650-91-3) → araU (3083-77-0)

Conditions	Yield
Stage #1: 1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one With hydrogenchloride; water at 80℃; for 2h; Stage #2: With sodium hydroxide pH=Ca. 7;	68%

uridine (58-96-8) → araU (3083-77-0)

Conditions	Yield
With bis(phenyl) carbonate; copper; sodium hydrogencarbonate In N,N-dimethyl-formamide at 140 - 150℃; for 45h;	58.5%
Multi-step reaction with 2 steps 1: 80 percent / diphenyl carbonate; NaHCO3 / dimethylformamide / 1.67 h / 140 °C 2: 95 percent / TFA / dimethylformamide / 10 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 79 percent / (C6H5O)2CO / dimethylformamide 2: 61 percent / LiOH View Scheme

diiminosuccinonitrile (28321-79-1) + uridine (58-96-8) → 2,2'-Anhydrouridine (3736-77-4) + araU (3083-77-0) + 2,2'-Anhydrouridine 3'-carbamate (87186-13-8) + 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione (6195-72-8)

Conditions	Yield
With diiminosuccinonitrile; Imidazole-HCl buffer at 2℃; for 96h; Further byproducts given;	A 10% B n/a C 54% D 5%

C15H24N2O6 → araU (3083-77-0)

Conditions	Yield
Stage #1: C15H24N2O6 With diethylamino-sulfur trifluoride In dichloromethane Stage #2: With hydrogenchloride In methanol; water	53%

bromocyane (506-68-3) + uridine (58-96-8) → 2,2'-Anhydrouridine (3736-77-4) + araU (3083-77-0) + 2,2'-Anhydrouridine 3'-carbamate (87186-13-8) + Uridine 3'-carbamate (89998-90-3)

Conditions	Yield
With triethylamine In water at 2℃; for 0.75h; Further byproducts given;	A 4% B 13% C 37% D 27%

bromocyane (506-68-3) + uridine (58-96-8) → 2,2'-Anhydrouridine (3736-77-4) + araU (3083-77-0) + 2,2'-Anhydrouridine 3'-carbamate (87186-13-8) + Uridine 3'-carbamate (89998-90-3) + 2'-O-carbamoyluridine (89998-91-4) + 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione (6195-72-8)

Conditions	Yield
With triethylamine In water at 2℃; for 0.75h; or with diiminosuccinonitrile;	A 2% B 13% C 37% D 27% E 2% F 4%

bromocyane (506-68-3) + uridine (58-96-8) → araU (3083-77-0) + 2,2'-Anhydrouridine 3'-carbamate (87186-13-8) + Uridine 3'-carbamate (89998-90-3) + 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione (6195-72-8)

Conditions	Yield
With triethylamine In water at 2℃; for 0.75h; Further byproducts given;	A 13% B 37% C 27% D 4%

uridine (58-96-8) → araU (3083-77-0) + 2,2'-Anhydrouridine 3'-carbamate (87186-13-8) + Uridine 3'-carbamate (89998-90-3) + 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione (6195-72-8)

Conditions	Yield
With bromocyane; triethylamine In water at 2℃; for 45h; Further byproducts given;	A 13% B 37% C 27% D 4%

uridine (58-96-8) → 2,2'-Anhydrouridine (3736-77-4) + araU (3083-77-0)

Conditions	Yield
With bis(phenyl) carbonate; copper; sodium hydrogencarbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 150℃; for 20h;	A 30% B 35%

diiminosuccinonitrile (28321-79-1) + uridine-5'-monophosphate sodium (3106-18-1) → 2,2'-Anhydrouridine (3736-77-4) + araU (3083-77-0) + 2,2'-Anhydrouridine 3'-carbamate (87186-13-8) + Uridine 3'-carbamate (89998-90-3)

Conditions	Yield
With Imidazole hydrochloride at 2℃; for 72h; Further byproducts given;	A 21% B 6% C 32% D 8%

diiminosuccinonitrile (28321-79-1) + uridine-5'-monophosphate sodium (3106-18-1) → 2,2'-Anhydrouridine (3736-77-4) + araU (3083-77-0) + 2,2'-Anhydrouridine 3'-carbamate (87186-13-8) + Uridine 3'-carbamate (89998-90-3) + 2'-O-carbamoyluridine (89998-91-4) + 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione (6195-72-8)

Conditions	Yield
With bovine alkaline phosphatase or with BrCN;	A 21% B 6% C 32% D 8% E 2% F 3%

5-iodouridine (1024-99-3) → araU (3083-77-0) + 1-β-D-arabinofuranosyl-5-iodouracil (3052-06-0)

Conditions	Yield
With bis(phenyl) carbonate; copper; sodium hydrogencarbonate In N,N-dimethyl-formamide at 140 - 150℃;

ara-UpUpU (112475-38-4) → araU (3083-77-0)

Conditions	Yield
With snake venom diasterease Product distribution;

O2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil (292037-79-7) → araU (3083-77-0)

Conditions	Yield
With sodium hydroxide In water Ambient temperature;

arabinosyl cytosine (147-94-4) → araU (3083-77-0) + uracil (66-22-8)

Conditions	Yield
With water at 90℃; Rate constant; pH 3.63;

ara-UpU (52769-97-8) → araU (3083-77-0)

Conditions	Yield
With snake venom diasterease Product distribution;

1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannyl pyrimidine-2,4(3H)-dione → 1-(β-D-arabinofuranosyl)-5-[125I]iodopyrimidin-2,4(3H)-dione + araU (3083-77-0)

Conditions	Yield
Stage #1: 1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannyl pyrimidine-2,4(3H)-dione With hexamethyldistannane; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 100℃; for 2h; Stage #2: With sodium methylate In methanol at 0℃; for 7h; Stage #3: With sodium hydroxide; sodium (¹²⁵I)iodide; acetic acid; dihydrogen peroxide In chloroform for 0.0166667h; Further stages.;

1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannyl pyrimidine-2,4(3H)-dione → araU (3083-77-0)

Conditions	Yield
With sodium methylate In methanol at 0℃; for 7h;

2',3'-O-isopropylidene-O2,5'-cyclouridine (3868-21-1) → araU (3083-77-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH, H2(17)O (54.75percent) / dimethylformamide 2: CF3COOH (90percent) 3: 79 percent / (C6H5O)2CO / dimethylformamide 4: 61 percent / LiOH View Scheme

2',3'-O-isopropylideneuridine (362-43-6) → araU (3083-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: CF3COOH (90percent) 2: 79 percent / (C6H5O)2CO / dimethylformamide 3: 61 percent / LiOH View Scheme
Multi-step reaction with 5 steps 1: pyridine 2: aqueous acetic acid 3: pyridine 4: methanol. NH3 5: aqueous H2SO4 View Scheme

tribenzoyl uridine (1748-04-5) → araU (3083-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / Et3N / methanol; H2O 2: 79 percent / (C6H5O)2CO / dimethylformamide 3: 61 percent / LiOH View Scheme

1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-chloro-2(1H)-pyrimidinone (4418-14-8) → araU (3083-77-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2(17)O (54.75percent) / CHCl3 2: 83 percent / Et3N / methanol; H2O 3: 79 percent / (C6H5O)2CO / dimethylformamide 4: 61 percent / LiOH View Scheme

ancitabine hydrochloride (10212-25-6) → araU (3083-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 M KOH / H2O / 0.33 h / Ambient temperature; pH=10.3 2: cytidine deaminase ( EC 3.5.4.5 ) / 48 h / 37 °C / pH=6.8 with acetic acid View Scheme

uridine-5'-monophosphate sodium (3106-18-1) → araU (3083-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / H2O / 1.33 h / 2 °C 2: 90 percent / H2O, triethylamine / 48 h / 60 °C View Scheme

araU (3083-77-0) + acetic anhydride (108-24-7) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil (14057-18-2)

Conditions	Yield
With dmap	100%
With dmap; triethylamine In acetonitrile at 20℃;	96%
With pyridine at 4℃; for 24h;	91%

araU (3083-77-0) + 2-Chloroadenosine (146-77-0) → 2-chloro-9-(β-D-arabinofuranosyl)adenine (10147-12-3)

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase for 48h; Enzymatic reaction;	99%

araU (3083-77-0) + inosine (58-63-9) → 9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one (7013-16-3)

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase for 48h; Enzymatic reaction;	98%

araU (3083-77-0) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-[(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (82845-94-1)

Conditions	Yield
With silver nitrate; triethylamine In 1,2-dimethoxyethane for 5h; Ambient temperature;	96%
With triethylamine; silver nitrate In 1,2-dimethoxyethane for 5h;	96%

araU (3083-77-0) → α-D-arabinofuranosyl-1-phosphate barium salt + uracil (66-22-8)

Conditions	Yield
Stage #1: araU With magnesium(II) chloride hexahydrate; recombinant E. coli uridine phosphorylase In aq. phosphate buffer at 40℃; for 72h; pH=7.0; Stage #2: With ammonium hydroxide; barium(II) acetate In aq. phosphate buffer at 4℃; pH=8.0;	A 96% B n/a

benzoyl cyanide (613-90-1) + araU (3083-77-0) → 1-(tri-O-benzoyl-β-D-arabinofuranosyl)-1H-pyrimidine-2,4-dione (4348-69-0)

Conditions	Yield
With triethylamine In acetonitrile for 2h; Ambient temperature;	95%

para-chlorotoluene (106-43-4) + araU (3083-77-0) → 1-(2,3,5-tri-O-p-toluyl-β-D-arabinofuranosyl)uracil (81777-54-0)

Conditions	Yield
In pyridine 1.) 0 degC to R.T., 2.) 50 degC, 2 h;	95%

araU (3083-77-0) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>-uracil (82845-98-5)

Conditions	Yield
With 3-picoline-N-oxide; silver nitrate In tetrahydrofuran for 2h; Ambient temperature;	95%
With 3-picoline-N-oxide; silver nitrate In tetrahydrofuran for 1.5h;	95%

araU (3083-77-0) → aBrUra (957-75-5, 3266-88-4, 3370-69-2, 38953-77-4, 82950-04-7)

Conditions	Yield
With N-Bromosuccinimide; sodium azide In 1,2-dimethoxyethane; water at 25℃; for 24h;	95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at 25℃; for 1h;	65%
With N-Bromosuccinimide In ethanol; chloroform; N,N-dimethyl-formamide

araU (3083-77-0) + 6-O-methylguanosine (7803-88-5) → 9-(β-D-Arabinofuranosyl)-2-amino-6-methoxy-9H-purine

Conditions	Yield
With potassium dihydrogenphosphate; uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase In aq. phosphate buffer at 52 - 55℃; for 168h; pH=7; Enzymatic reaction;	95%

araU (3083-77-0) + adenosine (58-61-7) → arabinosyl adenine (5536-17-4)

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase In aq. phosphate buffer at 52℃; for 16h; pH=7; Enzymatic reaction;	93%

araU (3083-77-0) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → arabinosyl adenine (5536-17-4)

Conditions	Yield
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0; several purine bases also investigated;	92%
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0;	92%
With potassium dihydrogenphosphate at 60℃; for 15h; Enterobacter aerogenes AJ 11125, pH 7.0;	87%

araU (3083-77-0) + 2-fluoroadenosine (146-78-1) → Fludarabine (146-78-1, 19768-92-4, 21679-14-1, 21679-15-2)

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase In aq. phosphate buffer at 52℃; pH=7; Enzymatic reaction;	92%

4,4'-dimethoxytrityl chloride (40615-36-9) + araU (3083-77-0) → 1-{(2R,3S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione (82854-27-1)

Conditions	Yield
With pyridine at -5℃; for 1h;	90%

araU (3083-77-0) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>-uracil (82845-98-5) + 1-[(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (82845-94-1) + 1-[(2R,3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (87418-77-7)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 40h; Product distribution; further solvents, reaction times, reagents, reagents and catalyst concentration,;	A 6% B 2% C 90%
With 1H-imidazole In N,N-dimethyl-formamide for 40h;	A 6% B 2% C 90%

araU (3083-77-0) + mono-4-methoxytrityl chloride (14470-28-1) → 5'-O-monomethoxytritylarabinouridine (87418-73-3)

Conditions	Yield
With pyridine at 50℃;	90%

araU (3083-77-0) → 1-(β-D-arabinofuranosyl)-5,6-dihydrouracil (30100-83-5)

Conditions	Yield
With hydrogen; Rh on carbon In water under 2400.2 Torr; for 16h; Ambient temperature;	90%

araU (3083-77-0) → 1-β-D-arabinofuranosyl-5-iodouracil (3052-06-0)

Conditions	Yield
With sodium azide; Iodine monochloride In acetonitrile at 25℃; for 36h;	90%
With ammonium cerium (IV) nitrate; iodine; acetic acid at 80℃; for 1h;	82%
With iodine; nitric acid In chloroform	62%
Multi-step reaction with 3 steps 1: 89 percent / pyridine / 0.5 h / 20 °C 2: 70 percent / I2; ceric(IV) ammonium nitrate / acetonitrile / 1 h / 80 °C 3: 80 percent / NaOMe / methanol / 0.5 h / 20 °C View Scheme
With iodine; nitric acid In chloroform

araU (3083-77-0) + propargyl bromide (106-96-7) → 1-(β-D-arabinofuranosyl)-3-(prop-2-yn-1-yl)uracil

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	90%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + araU (3083-77-0) → 5',3'-O-(tetraisopropyldisiloxane-1,3-di-yl)-1-β-D-arabinofuranosyl-uracil (104477-70-5)

Conditions	Yield
With pyridine at 0 - 20℃;	89%
With pyridine at 5 - 22℃; under 24 Torr; for 3h; regioselective reaction;	86%
With pyridine at 0 - 20℃;	60.3%
With pyridine
With pyridine

araU (3083-77-0) + acetic anhydride (108-24-7) → 1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-iodo-pyrimidine-2,4(3H)-dione (84500-33-4)

Conditions	Yield
Stage #1: araU; acetic anhydride With pyridine Stage #2: With ammonium cerium(IV) nitrate; iodine In acetonitrile	88%

araU (3083-77-0) + 2,6-diaminopurine (1904-98-9) → 2,6-diamino-9-(β-D-arabinofuranosyl)-purine (34079-68-0)

Conditions	Yield
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0;	83%
With dipotassium hydrogenphosphate; sodium azide; purine nucleoside phodphorylase ( EC 2.4.2.1 ); uridine phosphorylase ( EC 2.4.2.3 ) at 37℃; for 288h; pH=7.1; Yield given;
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Thermus thermophilus pyrimidine nucleoside phosphorylase In water at 70℃; for 3h; pH=7; Enzymatic reaction;

araU (3083-77-0) + propan-2-one O-butyryl oxime (133360-56-2) → 1-(5-O-butanoyl-β-D-arabinofuranosyl)uracil

Conditions	Yield
In tetrahydrofuran at 60℃; for 7h; lipase from Candida antarctica (CAL SP435L);	81%

N-Acetylimidazole (2466-76-4) + araU (3083-77-0) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil (14057-18-2)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 4h; pH=8;	78%

n-hexanoic anhydride (2051-49-2) + araU (3083-77-0) → 1-(5-O-hexanoyl-β-D-arabinofuranosyl)uracil + Hexanoic acid (2R,3S,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester

Conditions	Yield
In 1,4-dioxane for 3h; Ambient temperature; Lipase SP435;	A 77% B 3%

Upstream product

• 147-94-4 arabinosyl cytosine 
• 52769-97-8 ara-UpU 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 847650-91-3 1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one 
• 14057-18-2 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil 
• 56287-17-3 2'-deoxy-2'-fluorouridine 
• 31615-98-2 1-(3,5-Di-O-benzoyl-β-L-arabinofuranosyl)uracil 
• 1092978-60-3 Toluene-4-sulfonic acid (3R,4R,5R)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester 
• 58-96-8 uridine 
• 31615-96-0 3',5'-di-O-benzoyl-2,2'-anhydro-L-uridine 
• 35939-60-7 2-amino-β-L-arabinofurano[1',2':4,5]oxazoline 
• 31501-46-9 (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 95058-81-4 gemcitabine 
• 5536-17-4 arabinosyl adenine 

Downstream Products

• 1748-04-5 2',3',5'-tri-O-benzoyl-ara-L-uridine 
• 65-46-3 1-β-L-arabinofuranosyl cytosine 
• 1187056-79-6 1-(5-O-acetyl-β-D-arabinofuranosyl)uracil 
• 25383-79-3 1-(3,5-di-O-acetyl-β-D-arabinofuranosyl)uracil 
• 1228437-56-6 arabinouridine-5'-[phenyl-(benzoxy-D-alaninyl)]-phosphate 
• 1228437-59-9 arabinouridine-5'-[phenyl-(benzoxy-glycinyl)]-phosphate 
• 1228437-57-7 arabinouridine-5'-[phenyl-(benzoxy-L-alaninyl)]-phosphate 
• 13491-41-3 1-(β-D-Arabinofuranosyl)-4-hydroxylamino-2(1H)-pyrimidinon 
• 66-22-8 uracil 
• 6742-07-0 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine 
• 99519-13-8 Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-p-tolylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 82855-68-3 4-(p-tolylthio)-1-(β-D-arabinofuranosyl)pyrimidin-2(1H)-one 
• 82855-66-1 4-anilino-1-(β-D-arabinofuranosyl)pyrimidin-2(1H)-one 
• 82855-65-0 4-morpholino-1-(β-D-arabinofuranosyl)pyrimidin-2(1H)-one 

Relevant articles and documents

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Characterization of a novel resistance-related deoxycytidine deaminase from Brassica oleracea var. capitata

Brassica oleracea deoxycytidine deaminase (BoDCD), a deoxycytidine deaminase (DCD, EC 3.5.4.14) enzyme, is known to play an important role in the Trichoderma harzianum ETS 323 mediated resistance mechanism in young leaves of B. oleracea var. capitata during Rhizoctonia solani infection. BoDCD potentially neutralizes cytotoxic products of host lipoxygenase activity, and thereby BoDCD restricts the hypersensitivity-related programmed cell death induced in plants during the initial stages of infection. To determine the biochemical characteristics and to partially elucidate the designated functional properties of BoDCD, the enzyme was cloned into an Escherichia coli expression system, and its potential to neutralize the toxic analogues of 2′-deoxycytidine (dC) was examined. BoDCD transformants of E. coli cells were found to be resistant to 2′-deoxycytidine analogues at all of the concentrations tested. The BoDCD enzyme was also overexpressed as a histidine-tagged protein and purified using nickel chelating affinity chromatography. The molecular weight of BoDCD was determined to be 20.8 kDa as visualized by SDS-PAGE. The substrate specificity and other kinetic properties show that BoDCD is more active in neutralizing cytotoxic cytosine β-d-arabinofuranoside than in deaminating 2′-deoxycytinde to 2′-deoxyuridine in nucleic acids or in metabolizing cytidine to uridine. The optimal temperature and pH of the enzyme were 27 C and 7.5. The Km and Vmax values of BoDCD were, respectively, 91.3 μM and 1.475 mM for its natural substrate 2′-deoxycytidine and 63 μM and 2.072 mM for cytosine β-d-arabinofuranoside. The phenomenon of neutralization of cytotoxic dC analogues by BoDCD is discussed in detail on the basis of enzyme biochemical properties.

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METHODS AND REAGENTS FOR SYNTHESIZING NUCLEOSIDES AND ANALOGUES THEREOF

The present invention relates to methods and intermediates for the synthesis of nucleosides and nucleoside analogues (NAs). More specifically, the present invention relates to methods of synthesizing nucleosides and NAs, using simple achiral materials by a 'one-pot' proline-catalyzed halogenation of a heteroaryl-substituted acetaldehyde together with a tandem enantioselective aldol reaction followed by a reduction or organometallic addition and cyclization (annulation) reaction involving halide displacement.

MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF

The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside.

DEAMINATION OF ORGANOPHOSPHORUS-NUCLEOSIDES

The invention relates to a new synthethic process for obtaining compounds of formula (I) from compounds of formula (II) by means of cytidine deaminase enzymes.