Genetic information is stored in DNA as combinatorial codes held in nucleosides and nucleotides, in which form it is passed from parents to their offspring. Analogs of nucleosides and nucleotides are used clinically as medicinal agents such as reverse transcriptase inhibitors. Therefore, the preparation and development of these species as effective, selective and nontoxic antiviral and antitumor agents has been the subject of intense research.¹⁾
In addition to this, the development of Polymerase Chain Reaction (PCR) methodology has brought a dramatic change and rapid development in studies of DNA. At the current time the draft version in decoding and mapping human genome has been almost completed, and the functional analyses of genome and analyses of “Single Nucleotide Polymorphism” (SNP) are being vigorously pursued. Discovery of the RNAi process has facilitated the fast progression of studies of RNA. At the same time, chemically synthesized oligoDNA and oligoRNA have been studied as potential antisense DNAs, siRNAs and DNA aptamers; as oligonucleotide therapeutic agents, primers for PCR method, and elements of DNA computers.

Nucleosides and their analogs

Nucleotides and their analogs

Nucleobases and their analogs

Riboses and 2’-Deoxyriboses

Chemical Reagents for Pharmacology Research

Protecting Agents, Phosphorylating Agents & Condensing Agents

Enzymes and Coenzymes in Nucleic Acids

Nucleosides and their analogs

　Nucleosides are glycosylamines made by attaching a nucleobase to a ribose or 2’-deoxyribose ring, which can be phosphorylated producing nucleotides. Nucleosides analogues are an established class of clinically useful medicinal agents possessing a wide range of antiviral and anticancer activities. Consequently, extensive modifications have been made to both the heterocyclic base and the sugar moiety. Some representative examples of these are 9-[(2-Hydroxyethoxy)methyl]guanine (Acyclovir) developed by Elion in 1977, which shows antiviral activity; 3'-Azido-3'-deoxythymidine (AZT) discovered by Mitsuya et al. in 1985 and used for the treatment of HIV infection; and Cytosine β-D-arabinofuranoside (Cytarabine) approved by the FDA in 1969 and which has been shown to display a range anti-cancer activities. In addition, modified nucleosides such as 2’-Deoxy-5-methylcytidine are ubiquitous in living systems, and their functions have received due attention from the scientific community.
Protected nucleosides, in which reactive amino and hydroxyl groups have been masked, e.g. N⁶-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (Bz-DMT-dA), have been used for chemical synthesis of DNA and RNA.

B3404	A2073	T2690
T2691	T2692	T2549
D3580	D3065	D3581
D3066	I0702	I0703
I0704	D3614	D3615
D3642	D2235	D3610
D0046	D3583	D0048
D0052	D3584	D0060
C2207	C2208	A2054
A2135	C2192	F0656
I0759	A2052	D3579
D3566	A2033	B1575
B0666	F0635	F0534
F0636	I0258	M1931
M1405	A0559	C2206
H1290	A1915	A0152
C2035	C0522	C0525
G0171	I0037	L0217
I0700	I0697	I0699
B3102	B3087	B3094
B3101	B3103	B3093
B3460	R0077	T0233
T2511	U0020	V0098
X0008

B3404	(E)-5-(2-Bromovinyl)-2'-deoxyuridine
A2073	1-(3,5-Anhydro-2-deoxy-beta-D-threo-pentofuranosyl)thymine
T2690	2',3',5'-Tri-O-acetyl-2-amino-6-chloropurine Riboside
T2691	2',3',5'-Tri-O-acetyl-6-chloro-2-iodopurine Riboside
T2692	2',3',5'-Tri-O-acetylguanosine
T2549	2',3',5'-Tri-O-acetyluridine
D3580	2',3'-Didehydro-3'-deoxythymidine
D3065	2',3'-Dideoxyadenosine
D3581	2',3'-Dideoxycytidine
D3066	2',3'-Dideoxyinosine
I0702	2',3'-O-Isopropylideneadenosine
I0703	2',3'-O-Isopropylideneguanosine
I0704	2',3'-O-Isopropylideneinosine
D3614	2'-Deoxy-2'-fluorocytidine Hydrate
D3615	2'-Deoxy-2'-fluorouridine
D3642	2'-Deoxy-5-fluorocytidine
D2235	2'-Deoxy-5-fluorouridine
D3610	2'-Deoxy-5-methylcytidine
D0046	2'-Deoxyadenosine Monohydrate
D3583	2'-Deoxycytidine
D0048	2'-Deoxycytidine Hydrochloride
D0052	2'-Deoxyguanosine Hydrate
D3584	2'-Deoxyinosine
D0060	2'-Deoxyuridine
C2207	2,2'-O-Cyclocytidine Hydrochloride
C2208	2,2'-O-Cyclouridine
A2054	2-Amino-6-chloropurine Riboside
A2135	2-Aminoadenosine
C2192	2-Chloroadenosine Hydrate
F0656	2-Fluoroadenosine
I0759	2-Iodoadenosine
A2052	3'-Azido-3'-deoxythymidine
D3579	5'-Deoxy-5-fluorouridine
D3566	5'-O-(4,4'-Dimethoxytrityl)thymidine
A2033	5-Azacytidine
B1575	5-Bromo-2'-deoxyuridine
B0666	5-Bromouridine
F0635	5-Fluoro-1-(tetrahydro-2-furfuryl)uracil
F0534	5-Fluorocytidine
F0636	5-Fluorouridine
I0258	5-Iodo-2'-deoxyuridine
M1931	5-Methylcytidine
M1405	5-Methyluridine
A0559	6-Azauridine
C2206	6-Chloropurine Riboside
H1290	9-(2-Hydroxyethyl)adenine
A1915	Acyclovir
A0152	Adenosine
C2035	Cytarabine
C0522	Cytidine
C0525	Cytidine Sulfate
G0171	Guanosine
I0037	Inosine
L0217	Lamivudine
I0700	N2-Isobutyryl-2'-deoxyguanosine
I0697	N2-Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine
I0699	N2-Isobutyrylguanosine Monohydrate
B3102	N4-Benzoyl-2'-deoxycytidine
B3087	N4-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine
B3094	N4-Benzoylcytidine
B3101	N6-Benzoyl-2'-deoxyadenosine Hydrate
B3103	N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
B3093	N6-Benzoyladenosine
B3460	N6-Dibenzoyladenosine 2',3'-Dibenzoate
R0077	Ribavirin
T0233	Thymidine
T2511	Trifluorothymidine
U0020	Uridine
V0098	Vidarabine Monohydrate
X0008	Xanthosine Dihydrate

Nucleotides and their analogs

Nucleotides are formed from the condensation of nucleoside and a phosphate group. The　nucleosides themselves are formed from a nucleobase (see below) and a sugar moiety which is either ribose (RNA) or 2’-deoxyribose (DNA). Nucleotides are the minimum structural units of DNA and RNA, and serve as important cofactors in metabolism.

D3673	A0158	A2112
A2113	A0626	A0157
A0159	C0521	C0523
C1675	C0524	G0172
G0173	I0039	I0036
I0038	T0845	U0021
U0022	U0016

D3673	2'-Deoxycytidine 5'-Monophosphate Hydrate
A0158	5'-Adenylic Acid
A2112	Adenosine 3',5'-Cyclic Monophosphate Sodium Salt Hydrate
A2113	Adenosine 3'-Monophosphate Hydrate
A0626	Adenosine 5'-Diphosphate Disodium Salt Hydrate
A0157	Adenosine 5'-Triphosphate Disodium Salt Hydrate
A0159	Adenylic Acid Hydrate (2'- and 3'- mixture) from Yeast
C0521	Cytidine 3'-Monophosphate
C0523	Cytidine 5'-Diphosphate Trisodium Salt Hydrate
C1675	Cytidine 5'-Monophosphate
C0524	Cytidine-5'-monophosphate Disodium Salt
G0172	Guanosine 5'-Monophosphate Disodium Salt Hydrate
G0173	Guanylic Acid Sodium Salt (2'-,3'- mixture) from Yeast
I0039	Inosine 5'-Monophosphate Barium Salt Hydrate
I0036	Inosine 5'-Monophosphate Disodium Salt Hydrate
I0038	Inosine 5'-Triphosphate Trisodium Salt Hydrate
T0845	Thymidine 5'-Monophosphate Disodium Salt Hydrate
U0021	Uridine 5'-Monophosphate Disodium Salt Hydrate
U0022	Uridine 5'-Triphosphate Trisodium Salt
U0016	Uridylic Acid (2'- and 3'- mixture)

Nucleobases and their analogs

Nucleobases, usually simply called “bases”, are a vital sense component of DNA and RNA. The bases can be divided into two groups based on the structure: purines such as Adenine, Guanine; and pyrimidines such as Cytosine, Thymine, Uracil. Other nucleobases can be created by the modification of these basic structures. For example, Hypoxanthine and Xanthine are generated in living systems through deamination of Adenine and Guanine, respectively. Futhermore, nucleobase analogue 5-Fluorouracil (5-FU) is used as anticancer agents. Derivatives of 2-Fluoroadenine have been widely reported as prodrug forms of anti-cancer agents.

D1619	D1625	D2470
A1248	A1918	A1407
A1111	F0647	T0225
M2073	A2125	A2136
A0947	B0665	C0969
E0807	F0321	F0382
F0151	I0531	I0219
M0204	D3894	A0558
B3355	C2221	C2300
C2306	C0278	C2093
M0063	M1925	P0236
T0212	A0625	A0555
B3456	C0293	H1290
A0149	A0150	A0151
A0907	A2069	C0528
G0169	G0170	G0168
H0311	I0370	K0009
D3604	A2089	B3169
B3344	B1088	O0065
T0179	T0234	U0013
X0004

D1619	1,3-Dimethyl-6-chlorouracil
D1625	2,6-Diaminopurine Hydrate
D2470	2,6-Dichloropurine
A1248	2-Acetamido-6-hydroxypurine
A1918	2-Amino-5-chloropyrimidine
A1407	2-Amino-6-chloropurine
A1111	2-Aminopurine
F0647	2-Fluoroadenine
T0225	2-Thioxanthine
M2073	3-Methylxanthine
A2125	4-Amino-5-fluoro-2-methoxypyrimidine
A2136	4-Amino-6-chloropyrimidine
A0947	5-Aminoorotic Acid
B0665	5-Bromouracil
C0969	5-Chlorouracil
E0807	5-Ethyluracil
F0321	5-Fluorocytosine
F0382	5-Fluoroorotic Acid Monohydrate
F0151	5-Fluorouracil
I0531	5-Iodo-2,4-dimethoxypyrimidine
I0219	5-Iodouracil
M0204	5-Methylcytosine Hydrochloride
D3894	6-(Dimethylamino)purine
A0558	6-Azauracil
B3355	6-Benzyloxypurine
C2221	6-Chloro-2-fluoropurine
C2300	6-Chloro-3-methyluracil
C2306	6-Chloro-7-deazapurine
C0278	6-Chloropurine
C2093	6-Chlorouracil
M0063	6-Mercaptopurine Monohydrate
M1925	6-Methoxypurine
P0236	6-Phenyl-2-thiouracil
T0212	6-Thioguanine
A0625	8-Azaguanine
A0555	8-Azahypoxanthine
B3456	8-Bromotheophylline
C0293	8-Chlorotheophylline
H1290	9-(2-Hydroxyethyl)adenine
A0149	Adenine
A0150	Adenine Hydrochloride Hemihydrate
A0151	Adenine Sulfate Dihydrate
A0907	Allopurinol
A2069	Azathioprine
C0528	Cytosine
G0169	Guanine
G0170	Guanine Hydrochloride Hydrate
G0168	Guanine Sulfate Dihydrate
H0311	Hypoxanthine
I0370	Isoguanine
K0009	Kinetin
D3604	N2,9-Diacetylguanine
A2089	N4-Acetylcytosine
B3169	N4-Benzoylcytosine
B3344	N6-Benzoyladenine
B1088	N6-Benzyladenine
O0065	Orotic Acid Monohydrate
T0179	Theophylline
T0234	Thymine
U0013	Uracil
X0004	Xanthine

Riboses and 2’-Deoxyriboses

D and L Riboses and 2’-Deoxyriboses, and reagents for their protection are shown below.

T2607	T2641	D0059
R0082	R0067	R0083
R0080	R0025	R0068
M1965	R0026	R0066

T2607	1,2,3-Tri-O-acetyl-5-deoxy-beta-D-ribofuranose
T2641	1,3,5-Tri-O-benzoyl-alpha-D-ribofuranose
D0059	2-Deoxy-D-ribose
R0082	alpha-D-Ribose 1,5-Bis(phosphate) Tetrasodium Salt
R0067	beta-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate
R0083	beta-D-Ribose 1,5-Bis(phosphate) Tetrasodium Salt
R0080	beta-L-Ribofuranose 1-Acetate 2,3,5-Tribenzoate
R0025	D-(-)-Ribose
R0068	L-Ribose
M1965	Methyl beta-D-Ribofuranoside
R0026	Ribose-5-phosphate Barium Salt Hydrate
R0066	Tetra-O-acetyl-beta-D-ribofuranose

Chemical Reagents for Pharmacology Research

Typical nucleoside and nucleobase reagents used in pharmacology research are shown below.

B3404	D3580	D3065
D3581	D3066	D2235
A2052	D3579	A2033
B1575	F0635	F0321
F0151	F0636	I0258
M0063	T0212	A1915
A0907	A2069	C2035
K0009	L0217	R0077
T2511	V0098

B3404	(E)-5-(2-Bromovinyl)-2'-deoxyuridine
D3580	2',3'-Didehydro-3'-deoxythymidine
D3065	2',3'-Dideoxyadenosine
D3581	2',3'-Dideoxycytidine
D3066	2',3'-Dideoxyinosine
D2235	2'-Deoxy-5-fluorouridine
A2052	3'-Azido-3'-deoxythymidine
D3579	5'-Deoxy-5-fluorouridine
A2033	5-Azacytidine
B1575	5-Bromo-2'-deoxyuridine
F0635	5-Fluoro-1-(tetrahydro-2-furfuryl)uracil
F0321	5-Fluorocytosine
F0151	5-Fluorouracil
F0636	5-Fluorouridine
I0258	5-Iodo-2'-deoxyuridine
M0063	6-Mercaptopurine Monohydrate
T0212	6-Thioguanine
A1915	Acyclovir
A0907	Allopurinol
A2069	Azathioprine
C2035	Cytarabine
K0009	Kinetin
L0217	Lamivudine
R0077	Ribavirin
T2511	Trifluorothymidine
V0098	Vidarabine Monohydrate

Protecting Agents, Phosphorylating Agents & Condensing Agents

Silylation converts insoluble nucleobases into lipophilic trimethylsilyl compounds, which are readily soluble in organic solvents, permitting homogenous chemical reactions. The trimethylsilylated nucleobases react with protected sugars to afford nucleosides. The procedure is commonly referred to as the Hilbert-Johnson reaction modified by Vorbruggen et al.
Phosphorylating and phosphorothioating agents, condensing agents and protecting agents for hydroxyl group are of importance in the synthesis of DNA and RNA chains. Active research on chemical synthesis of DNA and RNA is being conducted, and a variety of synthetic methods using their agents are being developed. The dicyclohexylcarbodiimide (DCC) method exemplified by the Khorana group, the phosphotriester method and phosphitetriester method by the team of Letsinger and the phoshoramidite method by the Caruthers group are examples of the various synthetic methods. The corresponding and suitable agents have been developed and utilized. Condensing agents, 1,2,4-Triazole and 1H-Tetrazole, are also used for chemically conversion of Uridines into Cytidines.
Chemically synthesized DNA is becoming important as a primer for the PCR method, an antisense molecule or an element of the DNA computer.

Protecting Agents for Hydroxyl and Amino Groups

H0089	B1151	D1608
D2334	D2504	N0404
T1526	T1071	D1612
C0832	M0721	M0790
A0082	B0078	B0105
C0306	D2469	D3135
I0115	D1293	B0511
P0113	B0995	B1223
T0871	T0512	C0308

H0089	1,1,1,3,3,3-Hexamethyldisilazane
B1151	1,3-Benzodithiolylium Tetrafluoroborate [Hydroxyl-Protecting Agent]
D1608	1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane [Hydroxyl Protecting Agent]
D2334	1,3-Dichloro-1,1,3,3-tetramethyldisiloxane
D2504	2-Chlorotrityl Chloride
N0404	2-Nitrobenzyl Bromide
T1526	4,4',4''-Tris(4,5-dichlorophthalimido)trityl Bromide [Protecting Reagent for Primary Alcohol]
T1071	4,4',4''-Tris(benzoyloxy)trityl Bromide [Hydroxyl Protecting Agent]
D1612	4,4'-Dimethoxytrityl Chloride [Hydroxyl Protecting Agent]
C0832	4-Chlorophenoxyacetyl Chloride
M0721	4-Methoxybenzoyl Chloride
M0790	4-Methoxytrityl Chloride [Hydroxyl Protecting Agent]
A0082	Acetyl Chloride
B0078	Benzoic Anhydride
B0105	Benzoyl Chloride
C0306	Chlorotrimethylsilane
D2469	Di-tert-butyldichlorosilane
D3135	Di-tert-butylsilyl Bis(trifluoromethanesulfonate)
I0115	Isobutyryl Chloride
D1293	N,N-Dimethylformamide Dimethyl Acetal
B0511	N,O-Bis(trimethylsilyl)acetamide
P0113	Phenoxyacetyl Chloride
B0995	tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]
B1223	tert-Butyldiphenylchlorosilane
T0871	Trimethylsilyl Trifluoromethanesulfonate [Trimethylsilylating Agent]
T0512	Trityl Bromide
C0308	Trityl Chloride

Phosphorylating and Phosphorothioating Agents

C1215	C1250	C1210
C0976	C2228	B3125
C0977	C0978	D2624
D0624	D0764	D1059
M0905	M0904	P0209
P1223

C1215	2-Chloro-1,3,2-dioxaphospholane
C1250	2-Chloro-2-oxo-1,3,2-dioxaphospholane
C1210	2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one
C0976	2-Chlorophenyl Phosphorodichloridate [Phosphorylating Agent]
C2228	2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite
B3125	3H-1,2-Benzodithiol-3-one 1,1-Dioxide
C0977	4-Chlorophenyl Phosphorodichloridate [Phosphorylating Agent]
C0978	Barium 2-Cyanoethylphosphate Hydrate [Phosphorylating Agent]
D2624	Dibenzyl N,N-Diisopropylphosphoramidite
D0624	Diethyl Chlorothiophosphate
D0764	Dimethyl Chlorothiophosphate
D1059	Diphenyl Chlorophosphate
M0905	Methyl Dichlorophosphite [Phosphitylating Agent]
M0904	Methyl Phosphorodichloridate
P0209	Phenyl Dichlorophosphate
P1223	Tetrabenzyl Pyrophosphate

Condensing Agents

C2325	T0340	T1410
N0604	T1985	T1562
T0459	M1186	M0071
N0477	D2026	B3020
E0670	M0625	D3792
D0436

C2325	1,1'-Carbonyldi(1,2,4-triazole)
T0340	1,2,4-Triazole
T1410	1-(2,4,6-Triisopropylbenzenesulfonyl)imidazole
N0604	1-(4-Nitrobenzenesulfonyl)-1H-1,2,4-triazole
T1985	1-(p-Toluenesulfonyl)imidazole
T1562	2,4,5,6-Tetramethylbenzenedisulfonyl Dichloride
T0459	2,4,6-Triisopropylbenzenesulfonyl Chloride
M1186	2,4-Mesitylenedisulfonyl Dichloride
M0071	2-Mesitylenesulfonyl Chloride
N0477	3-Nitro-1,2,4-triazole [Coupling Agent]
D2026	4,5-Dicyanoimidazole
B3020	5-(Benzylthio)-1H-tetrazole
E0670	5-(Ethylthio)-1H-tetrazole
M0625	Mesitylenesulfonylimidazole
D3792	N,N'-Dicyclohexyl-4-morpholinecarboxamidine
D0436	N,N'-Dicyclohexylcarbodiimide [for Peptide Synthesis]

Enzymes and Coenzymes in Nucleic Acids

D0919	beta-Nicotinamide Adenine Dinucleotide Hydrate, oxidized form
D0920	beta-Nicotinamide Adenine Dinucleotide Disodium Salt Hydrate, reduced form
C0379	beta-Nicotinamide Adenine Dinucleotide Phosphate Sodium Salt Hydrate, oxidized form
T0521	beta-Nicotinamide Adenine Dinucleotide Phosphate Tetrasodium Salt reduced form
P0251	Phosphatase, Acid from Wheat Germ