50-89-5

Basic information

• Product Name: Thymidine
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-5-methyl-;2-Desoxy-thymidine;5-Methyldeoxyurindine;beta-D-Ribofuranoside, thymine-1 2-deoxy-;Deoxythymidin;Deoxythymidine;Desoxy-thymidin;Dthyd
• CAS NO: 50-89-5
• Molecular Formula: C₁₀H₁₄N₂O₅
• Molecular Weight: 242.23
• EINECS: 200-070-4
• Product Categories: FINE Chemical & INTERMEDIATES;Pyridines, Pyrimidines, Purines and Pteredines;chiral;API intermediates;Zidovudine;Stavudine;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Anti-virals;Bases & Related Reagents;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Miscellaneous Specialties;Pyrimidine purine;nucleoside
• Mol File: 50-89-5.mol
• Article Data: 197

Chemical Properties

• Melting Point: 186-188 °C(lit.)
• Boiling Point: 385.05°C (rough estimate)
• Appearance: White to almost white/Crystalline Powder
• Density: 1.3129 (rough estimate)
• Refractive Index: 33 ° (C=1, 1mol/L NaOH)
• Storage Temp.: 0-6°C
• Solubility: Acetone, DMSO (Slightly), Ethanol, Ethyl Acetate, Methanol (Slightly, Heated), P
• PKA: pK1:9.79;pK2:12.85 (25°C)
• Water Solubility: SOLUBLE
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9397
• BRN: 89285
• CAS DataBase Reference: Thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine(50-89-5)
• EPA Substance Registry System: Thymidine(50-89-5)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-40-36/37/38-68
• Safety Statements: 22-24/25-37/39-26-36/37/39
• WGK Germany: 3
• RTECS: XP2071000
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 50-89-5(Hazardous Substances Data)

Usage

Description

Thymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. In cell biology it is used to synchronize the cells in G1/early S phase.

Chemical Properties

White crystalline powder

Uses

Different sources of media describe the Uses of 50-89-5 differently. You can refer to the following data:
1. Constituent of deoxyribonucleic acid
2. Used for e.g. syntheses of zidovudine. Attributes For further information please contact us Contact
3. Thymidine is used in the syntheses of active pharmaceutical ingredient such as zidovudine. It also pairs with deoxyadenosine in double-stranded deoxyribonucleic acid. It is used to synchronize the cells in G1/early S phase in cell biology.

Definition

Different sources of media describe the Definition of 50-89-5 differently. You can refer to the following data:
1. The nucleoside (deoxyriboside) of thymine. Occurs in DNA.
2. The NUCLEOSIDE formed when thymine is linked to D-ribose by a β-glycosidic bond.
3. thymidine: A nucleoside consistingof one thymine molecule linked to ad-doxyribose sugar molecule.

General Description

Thymidine is also referred to as pyrimidine deoxynucleoside. Deoxythymidine is a nucleoside present in DNA. In a DNA double stranded structure, thymidine pairs with deoxyadeninosine.

Biochem/physiol Actions

Thymidine is useful in cell synchronization during S-phase. In the salvage pathway of pyrimidines, pyrimidine phosphorylase reversibly converts thymine to thymidine.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise -thymidine from ethyl acetate, MeOH/Et2O (m 188o) or H2O (as 2H2O m 189o). It is soluble in water and hot organic solvents. The picrate has m 230o (from EtOH).

InChI:InChI=1/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7-,8+/m1/s1

Synthetic route

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → thymidine (50-89-5)

Conditions	Yield
With zinc dibromide In nitromethane for 0.0166667h; Ambient temperature;	100%
With zinc dibromide In nitromethane Kinetics; Ambient temperature; in various solvent:CH2Cl2, THF, Acetone, Dioxane; other 5'-deoxytritylnucleosides;	100%
With β-naphthol In dichloromethane for 0.166667h; Product distribution / selectivity; Irradiation with mercury arc lamp;	97%

5'-O-tritylthymidine (7791-71-1) → thymidine (50-89-5)

Conditions	Yield
With silica gel; trifluoroacetic acid In methanol; chloroform	100%
Stage #1: 5'-O-tritylthymidine With carbon tetrabromide In methanol for 0.5h; Irradiation; Stage #2: In methanol at 20℃; for 12.5h;	97%
With carbon tetrabromide In methanol at 20℃; for 13h; Irradiation;	97%

1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[2-(4-hydroxyphenyl)-2-oxoethoxy]tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione (1335224-06-0) → thymidine (50-89-5)

Conditions	Yield
In methanol; water for 0.00416667h; Photolysis;	100%

3',5'-diacetylthymidine (6979-97-1, 97834-40-7, 142405-86-5) → thymidine (50-89-5)

Conditions	Yield
With lipase A from Aspergillus niger In aq. phosphate buffer; acetonitrile at 25℃; for 2h; pH=7; Enzymatic reaction;	99%
With ammonium hydroxide at 20℃; Inert atmosphere;
With methanol; sodium methylate at 44℃; under 760.051 Torr; for 1h; Large scale reaction;	295.6 g
With methanol; sodium methylate for 1h; Reflux;

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → thymidine (50-89-5)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide for 1h; Ambient temperature;	98%
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;	95%
With acetyl chloride In methanol for 2.5h;	90%

thymidine 5'-(3'',5''-dimethoxybenzoin)carbonate (167872-02-8) → thymidine (50-89-5)

Conditions	Yield
In benzene for 1h; Irradiation;	98%

5'-O-(9-phenylthioxanthyl)-2'-deoxythimidine (82161-35-1) → thymidine (50-89-5)

Conditions	Yield
In water; acetonitrile Hydrolysis; Irradiation;	97%

3',5'-diacetylthymidine (6979-97-1, 97834-40-7, 142405-86-5) + p2(Ac-Cys-(Asp)4-Asp-COOH)-modified immobilized BTL*S196C enzyme → 5'-O-acetylthymidine (35898-31-8) + thymidine (50-89-5)

Conditions	Yield
With sodium acetate In acetonitrile at 25℃; for 100h; pH=5; pH-value; Time; Reagent/catalyst; regioselective reaction;	A 97% B 3%

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) → thymidine (50-89-5)

Conditions	Yield
With Decaborane In tetrahydrofuran; methanol at 20℃; for 6h;	96%
With iodine(I) bromide In methanol; dichloromethane for 2h; Ambient temperature;	95%
With potassium tert-butylate In N,N-dimethyl-formamide for 24h; Ambient temperature;	92%

C23H31BN2O7 → thymidine (50-89-5)

Conditions	Yield
With dihydrogen peroxide In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 0.333333h; pH=7.2; Reagent/catalyst;	96%

3-methylthymidine (958-74-7) → thymidine (50-89-5)

Conditions	Yield
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction;	94%

5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)thymidine (166758-13-0) → thymidine (50-89-5)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide for 1.5h; Ambient temperature;	93%

5'-O-trityl-3'-O-tert-butyldimethylsilyl thymidine (213552-25-1) → thymidine (50-89-5)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide for 1h; Ambient temperature;	93%

Carbonic acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-trimethylsilanyl-ethyl ester (78687-52-2) → ethene (74-85-1) + trimethylsilyl fluoride (420-56-4) + thymidine (50-89-5)

Conditions	Yield
zinc dibromide In tetrahydrofuran at 20℃; for 0.166667h; deprotection of TMSEC derivat with various catalyst;	A n/a B n/a C 92%

5'-O-(4-monomethoxytrityl)-2'-deoxythymidine (42926-80-7) → thymidine (50-89-5)

Conditions	Yield
With cerium(IV) triflate; water In acetonitrile at 25℃; for 0.5h;	92%
With zinc dibromide In nitromethane Kinetics; Ambient temperature;
Multi-step reaction with 7 steps 1: 82 percent / 1.)collidine 2.)I2, H2O / tetrahydrofuran 2: 91 percent 3: 25 percent / 1.)Dowex(Py+) 2.)Ph3P-CCl4 4: 76 percent / NaH/CS2 / dimethylformamide 5: 80 percent / 80percent acetic acid 6: ClCN/H2O/collidine / tetrahydrofuran 7: snake venom phosphodiesterase View Scheme

phenacyl 5'-thymidine carbonate (252979-74-1) → thymidine (50-89-5)

Conditions	Yield
With 9,10-dimethylanthracene In acetonitrile for 4h; UV-irradiation;	91%
With N-methylcarbazole In acetonitrile for 4h; UV-irradiation;	81%
In acetonitrile for 3h; UV-irradiation;

3',5'-diacetylthymidine (6979-97-1, 97834-40-7, 142405-86-5) + BTL*-A193C enzyme → 3'-O-acetylthymidine (21090-30-2) + 5'-O-acetylthymidine (35898-31-8) + thymidine (50-89-5)

Conditions	Yield
With sodium acetate In acetonitrile at 25℃; for 72h; pH=5; regioselective reaction;	A 91% B 3% C 6%

2'-bromo-2'-deoxy-5-methyluridine → thymidine (50-89-5)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol; toluene at 45℃; under 2068.65 Torr; for 6h;	90.9%

2'-chlorothymidine (54898-34-9) → thymidine (50-89-5)

Conditions	Yield
With hydrogen; nickel In aq. phosphate buffer at 40℃; under 760.051 Torr; for 8h; pH=7.2; Reagent/catalyst; Temperature; pH-value; Green chemistry;	90.3%

2'-bromothymidine (95585-76-5) → thymidine (50-89-5)

Conditions	Yield
With hydrogen; nickel In methanol under 2327.2 Torr;	90%
With hydrogen; nickel In aq. phosphate buffer at 10 - 20℃; under 760.051 Torr; for 10h; pH=7.4; Green chemistry;	38.6g

3',5'-bis-O-(tert-butyldiphenylsilyl)-thymidine (118068-35-2) → thymidine (50-89-5)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide for 1h; Ambient temperature;	89%

5-(benzyloxy)methyl-2′-deoxyuridine (19083-35-3) → thymidine (50-89-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 0.5h; Inert atmosphere;	88%

3',5'-di-O-levulinylthymidine (440327-37-7) → 3'-O-levulinoylthymidine (78635-98-0) + thymidine (50-89-5)

Conditions	Yield
With Candida antarctica lipase B; phosphate buffer In 1,4-dioxane at 40℃; for 24h; pH=7;	A 85% B n/a

5-Methyluridine (1463-10-1) → thymidine (50-89-5)

Conditions	Yield
With bis(phenyl) carbonate; sodium hydrogencarbonate In water; ethyl acetate; N,N-dimethyl-formamide for 1h; Heating / reflux;	85%
With hydrogenchloride; hydrogen; nickel; carbonic acid dimethyl ester; sodium hydroxide In methanol; N,N-dimethyl acetamide at 50 - 110℃; under 4500.45 Torr; for 28h; Solvent; Reagent/catalyst; Temperature; Pressure; Industrial scale;
Multi-step reaction with 3 steps 1: sodium hydroxide; Diethyl carbonate / N,N-dimethyl-formamide / 8 h / 120 °C 2: hydrogen bromide / N,N-dimethyl-formamide / 4 h / 40 °C 3: hydrogen; nickel / aq. phosphate buffer / 10 h / 10 - 20 °C / 760.05 Torr / pH 7.4 / Green chemistry View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide; Diethyl carbonate / N,N-dimethyl-formamide / 8 h / 120 °C 2: hydrogenchloride / N,N-dimethyl acetamide / 5 h / 60 °C 3: hydrogen; nickel / aq. phosphate buffer / 8 h / 40 °C / 760.05 Torr / pH 7.2 / Green chemistry View Scheme

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 3'-O-(t-butyldimethylsilyl)thymidine (40733-27-5) + thymidine (50-89-5)

Conditions	Yield
With phosphomolybdic acid In methanol at 20℃; for 3h; Solvent; Reagent/catalyst; regioselective reaction;	A 85% B 9%

3',5'-di-O-methoxyacetylthymidine (92447-12-6) → thymidine (50-89-5)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;	84%

N3-benzoyl thymidine (94189-75-0) → thymidine (50-89-5)

Conditions	Yield
With benzyl alcohol at 90℃; for 30h;	82%
With ammonium hydroxide for 1h; Ambient temperature;

3',5'-diacetylthymidine (6979-97-1, 97834-40-7, 142405-86-5) + p6(Ac-Cys-(Phe-Gly)2-Asp-Asp-CONH2)-modified immobilized BTL*-S196C enzyme → 3'-O-acetylthymidine (21090-30-2) + 5'-O-acetylthymidine (35898-31-8) + thymidine (50-89-5)

Conditions	Yield
With sodium acetate In acetonitrile at 25℃; for 48h; pH=5; regioselective reaction;	A 2% B 82% C 16%

C31H33N3O5 (1220688-60-7) → thymidine (50-89-5)

Conditions	Yield
With methanol for 1h; UV-irradiation;	81%

acetic anhydride (108-24-7) + thymidine (50-89-5) → 3',5'-diacetylthymidine (6979-97-1, 97834-40-7, 142405-86-5)

Conditions	Yield
With pyridine for 2h;	100%
With pyridine at 20℃;	99%
With dmap	98%

chloro-trimethyl-silane (75-77-4) + thymidine (50-89-5) → 3',5'-O-bis-(trimethylsilyl)-thymidine (10457-18-8)

Conditions	Yield
With pyridine; N-ethyl-N,N-diisopropylamine at 20℃; for 0.5h;	100%
With N-ethyl-N,N-diisopropylamine In pyridine for 0.5h; Ambient temperature;
With pyridine at 20℃;

Isopropenyl acetate (108-22-5) + thymidine (50-89-5) → 5'-O-acetylthymidine (35898-31-8)

Conditions	Yield
With subtilisin 8350 In N,N-dimethyl-formamide at 45℃; for 36h;	100%

tert-butyldimethylsilyl chloride (18162-48-6) + thymidine (50-89-5) → 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 5h;	100%
With silver nitrate In tetrahydrofuran	98%
With dmap In pyridine at 20℃; for 10h;	97%

tert-butyldimethylsilyl chloride (18162-48-6) + thymidine (50-89-5) → 3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 25℃;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	100%
With pyridine; 1H-imidazole Inert atmosphere;	100%

tert-butylchlorodiphenylsilane (58479-61-1) + thymidine (50-89-5) → 5'-O-tert-butyldiphenylsilylthymidine (101527-40-6)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at -50 - 20℃; for 4h;	100%
With pyridine; dmap for 6h; Ambient temperature;	95%
With dmap In pyridine for 48h; Ambient temperature;	93%

4-bromo-1-fluorobutane (462-72-6) + thymidine (50-89-5) → N-3-(4-fluoro-n-butyl)thymidine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 20℃; for 72h;	100%

mono-4-methoxytrityl chloride (14470-28-1) + thymidine (50-89-5) → 5'-O-(4-monomethoxytrityl)-2'-deoxythymidine (42926-80-7)

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 3.5h;	99%
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	97%
With pyridine	94%

thymidine (50-89-5) → 2'-deoxy-5-(trideuteriomethyl)uridine (74848-84-3)

Conditions	Yield
With d(4)-methanol; palladium on activated charcoal; hydrogen at 160℃; for 24h;	99%
With deuterium; platinum(IV) oxide In water-d2 at 75 - 80℃; for 72h;	85%
With hydrogen; water-d2; platinum(IV) oxide at 50 - 60℃; for 192h;	75%

thymidine (50-89-5) → 5’-bromo-5’-deoxythymidine (25905-51-5)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In N,N-dimethyl acetamide at 20℃; for 5.5h; Appel Halogenation; Inert atmosphere;	99%
With carbon tetrabromide; triphenylphosphine In pyridine for 1h;	66%

triisopropylsilyl chloride (13154-24-0) + thymidine (50-89-5) → (+)-5-methyl-1-((2R,4S,5R)-4-((triisopropylsilyl)oxy)-5-(((triisopropyl-silyl)oxy)methyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione (54925-58-5)

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 50℃; for 16h;	99%

methanesulfonyl chloride (124-63-0) + thymidine (50-89-5) → 3',5'-dimethanesulfonylthymidine

Conditions	Yield
With pyridine In water	98.6%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + thymidine (50-89-5) → 1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]thymine (97626-18-1)

Conditions	Yield
With pyridine at 20℃; for 24h;	98%
With pyridine at 20℃; for 4h; Inert atmosphere;	95%
With pyridine for 0.333333h; Ambient temperature;	85%
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 0℃; for 4h;	49.9 g
With pyridine at 20℃; for 40h; Inert atmosphere;

thymidine (50-89-5) → 5,6-dihydrothymidine (5627-00-9)

Conditions	Yield
With Rh/Al2O3; hydrogen In methanol; water for 168h;	98%
With hydrogen; Rh/Al2O3 In methanol; water under 2585.7 Torr; for 48h;	96%
With Rh/Al2O3; hydrogen In water at 20℃; under 22502.3 Torr;	85%

2,2-dimethylpropanoic anhydride (1538-75-6) + thymidine (50-89-5) → 3',5'-O-bis(trimethylacetyl)thymidine

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In dichloromethane; water at 25℃; for 24h;	98%

vinyl benzoate (769-78-8) + thymidine (50-89-5) → 5'-benzoylthymidine (35898-29-4, 65475-51-6)

Conditions	Yield
With Candida antarctica lipase B In tetrahydrofuran at 60℃; for 63h;	98%
With Candida antarctica lipase B In tetrahydrofuran at 60℃; for 116h; Inert atmosphere; Enzymatic reaction; regioselective reaction;	93%

thymidine (50-89-5) + 5-((tert-butoxycarbonyl)amino)-4-oxopentanoic acid (72072-06-1) → 3',5'-di-O-(Boc-ALA)thymidine (1131245-46-9)

Conditions	Yield
With dmap; triethylamine; dicyclohexyl-carbodiimide In 1,4-dioxane; dichloromethane at 0 - 20℃;	98%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + thymidine (50-89-5) → 5-methyl-1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

Conditions	Yield
In pyridine at 20℃; for 24h;	98%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + thymidine (50-89-5) → 1-[(6aS,8R,9aR)-2,2,4,4-tetraisopropyl-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methylpyrimidine-2,4-dione (137174-38-0)

Conditions	Yield
With pyridine at 20℃; for 24h;	98%

trityl chloride (76-83-5) + thymidine (50-89-5) → 5'-O-tritylthymidine (7791-71-1)

Conditions	Yield
With pyridine at 20℃; for 21.5h;	97.1%
In pyridine at 20℃; for 48h;	92%
With pyridine at 100℃; for 0.5h;	91%

4,4'-dimethoxytrityl chloride (40615-36-9) + thymidine (50-89-5) → 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2)

Conditions	Yield
With pyridine; dmap at 20℃; for 5h;	97%
With pyridine; dmap at 20℃; for 24h;	96%
With pyridine at 20℃; for 12h;	96%

4-methyl-benzoyl chloride (874-60-2) + thymidine (50-89-5) → 3',5'-di-O-toluoylthymidine (4449-39-2)

Conditions	Yield
With pyridine for 3h; Ambient temperature;	97%
With pyridine at 20℃; for 1h;	96%
at 0 - 55℃;
With dmap In dichloromethane

3,4,5,6-tetrachlorophthalimide (1571-13-7) + thymidine (50-89-5) → 4,5,6,7-Tetrachloro-2-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-isoindole-1,3-dione (210490-66-7)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Mitsunobu reaction;	97%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran	97%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran	97%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 0.25h;

Upstream product

• 102198-09-4 Hexanoic acid (2R,3S,5R)-2-hexanoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 43179-29-9 (5R,6R)-trans-(+)-5-bromo-6-hydroxy-5,6-dihydrothymidine 
• 364776-73-8 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]thymidine 
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• 153-18-4 rutin 
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• 855743-26-9 5'-O-({[2-(2-nitrophenyl)-5-(9-oxo-9H-thioxanthen-2-yl)pentyl]oxy}carbonyl)thymidine 
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• 179691-39-5 5'-O-(2-(2-chloro-6-nitrophenyl)ethoxycarbonyl)thymidine 

Downstream Products

• 111160-28-2 1-(5-chloro-2,5-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one 
• 109389-25-5 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one 
• 90029-85-9 3-(3-oxoprop-1-enyl)thymidine 
• 61552-42-9 Thiamiprine 2'-deoxyriboside 
• 452-51-7 D-2-deoxyribose 
• 76945-38-5 (2S)-amino-6-(1-thyminyl)hexanoic acid 
• 102093-86-7 O⁴-(4-nitrophenylsulfonylethyl)thymidine 
• 124656-50-4 3,5-Dinitro-benzoic acid (1R,9R,10R)-4-methyl-5-oxo-8,11-dioxa-2,6-diaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-10-ylmethyl ester 
• 97626-18-1 1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]thymine 
• 92220-88-7 thymidine 5'- 
• 138395-79-6 5'-O-deoxythymidine 
• 63914-08-9 3',5'-bis-O-(p-tolylsulfonyl)thymidine 
• 92220-87-6 thymidine 5'- 
• 17331-53-2 3'-O-benzoylthymidine 

Relevant articles and documents

An Improved Approach for Practical Synthesis of 5-Hydroxymethyl-2′-deoxycytidine (5hmdC) Phosphoramidite and Triphosphate

5-Hydroxymethyl-2′-deoxycytidine (5hmdC) phosphoramidite and triphosphate are important building blocks in 5hmdC-containing DNA synthesis for epigenetic studies. However, efficient and practical methods for the synthesis of these compounds are

Biochemical characterization of a recombinant acid phosphatase from Acinetobacter baumannii

Genomic sequence analysis of Acinetobacter baumannii revealed the presence of a putative Acid Phosphatase (AcpA; EC 3.1.3.2). A plasmid construct was made, and recombinant protein (rAcpA) was expressed in E. coli. PAGE analysis (carried out under denaturing/ reducing conditions) of nickel-affinity purified protein revealed the presence of a nearhomogeneous band of approximately 37 kDa. The identity of the 37 kDa species was verified as rAcpA by proteomic analysis with a molecular mass of 34.6 kDa from the deduced sequence. The dependence of substrate hydrolysis on pH was broad with an optimum observed at 6.0. Kinetic analysis revealed relatively high affinity for PNPP (Km = 90 μM) with Vmax, kcat, and Kcat/Km values of 19.2 pmoles s-1, 4.80 s-1(calculated on the basis of 37 kDa), and 5.30 × 104 M-1s-1, respectively. Sensitivity to a variety of reagents, i.e., detergents, reducing, and chelating agents as well as classic acid phosphatase inhibitors was examined in addition to assessment of hydrolysis of a number of phosphorylated compounds. Removal of phosphate from different phosphorylated compounds is supportive of broad, i.e., 'nonspecific' substrate specificity; although, the enzyme appears to prefer phosphotyrosine and/or peptides containing phosphotyrosine in comparison to serine and threonine. Examination of the primary sequence indicated the absence of signature sequences characteristic of Type A, B, and C nonspecific bacterial acid phosphatases.

Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine

Despite its importance in the design of photocaged molecules, less attention is focused on linker chemistry than the cage itself. Here, we describe unique uncaging properties displayed by two coumarin-caged thymidine compounds, each conjugated with (2) or without (1) an extended, self-immolative spacer. Photolysis of 1 using long-wavelength UVA (365 nm) or visible (420, 455 nm) light led to the release of free thymidine along with the competitive generation of a thymidine-bearing recombination product. The occurrence of this undesired side reaction, which is previously unreported, was not present with the photolysis of 2, which released thymidine exclusively with higher quantum efficiency. We propose that the spatial separation between the cage and the substrate molecule conferred by the extended linker can play a critical role in circumventing this unproductive reaction. This report reinforces the importance of linker selection in the design of coumarin-caged oligonucleosides and other conjugates.