DNA / RNA Synthesis

Studies on DNA have made great strides since Watson and Crick proposed the double helix structure of DNA in 1953.1) Studies on genes have achieved rapid progress with dramatic developments in genetic engineering represented by genetic modification and cloning. In line with these trends, vigorous research on chemical synthesis of DNA is being conducted, and a variety of synthetic methods are being developed. The dicyclohexylcarbodiimide (DCC) method2) by Khorana group, the phosphotriester method3) and phosphite-triester method4) by Letsinger group and the phoshoramidite method5) by Caruthers group are examples of the various synthetic methods. The corresponding, suitable protecting agents, phosphorylating agents, condensing agent, and deprotecting agents have been developed and utilized.
In 1983 Mullis devised the Polymerase Chain Reaction (PCR) method6) making the replication reaction process of DNA much easier. This PCR method brought a dramatic change and rapid development in the studies of DNA. Today 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 performed. Genomic drug discovery, gene test, tailor made therapy, are being advanced.
Chemically synthesized DNA is becoming important as a primer for the PCR method, an antisense molecule or an element of the DNA computer.

Nucleotides

Nucleosides

Bases

Phosphorylating Agents

Condensing Agents

Protecting Agents for hydroxyl group

Nucleotides

D3673 D3673 A0158 A0158 T0844 T0844
A2112 A2112 A2113 A2113 A0157 A0157
A0626 A0626 C0521 C0521 C0523 C0523
C1675 C1675 C0524 C0524 G0172 G0172
I0036 I0036 I0038 I0038 T0845 T0845
U0021 U0021 U0022 U0022
D3673 2'-Deoxycytidine 5'-Monophosphate Hydrate
A0158 5'-Adenylic Acid
T0844 5'-Thymidylic Acid Calcium Salt
A2112 Adenosine 3',5'-Cyclic Monophosphate Sodium Salt Hydrate
A2113 Adenosine 3'-Monophosphate Hydrate
A0157 Adenosine 5'-Triphosphate Disodium Salt Hydrate
A0626 Adenosine-5'-diphosphate Disodium Salt Hydrate
A0159 Adenylic Acid Hydrate (2'- and 3'- mixture) from Yeast
C0521 Cytidine 3'-Monophosphate
C0523 Cytidine 5'-Diphosphate Trisodium Salt
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) (Yeast)
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)
Page Top

Nucleosides

D3580 D3580 D3065 D3065 D3581 D3581
D3066 D3066 I0702 I0702 I0703 I0703
I0704 I0704 D3614 D3614 D3615 D3615
D3642 D3642 D2235 D2235 D3610 D3610
D0046 D0046 D3583 D3583 D0048 D0048
D0052 D0052 D3584 D3584 D0060 D0060
C2207 C2207 C2208 C2208 A2054 A2054
A2135 A2135 C2192 C2192 F0656 F0656
A2052 A2052 D3579 D3579 D3566 D3566
A2033 A2033 B1575 B1575 B0666 B0666
F0635 F0635 F0534 F0534 F0636 F0636
I0258 I0258 M1931 M1931 M1405 M1405
A0559 A0559 C2206 C2206 A1915 A1915
A0152 A0152 C2035 C2035 C0522 C0522
C0525 C0525 G0171 G0171 I0037 I0037
L0217 L0217 I0700 I0700 I0697 I0697
I0699 I0699 B3102 B3102 B3087 B3087
B3094 B3094 B3101 B3101 B3103 B3103
B3093 B3093 R0077 R0077 T0233 T0233
T2511 T2511 U0020 U0020 V0098 V0098
X0008 X0008
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
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
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
R0077 Ribavirin
T0233 Thymidine
T2511 Trifluorothymidine
U0020 Uridine
V0098 Vidarabine Monohydrate
X0008 Xanthosine
Page Top

Bases

D1619 D1619 D2470 D2470 A1407 A1407
A1111 A1111 F0647 F0647 T0225 T0225
A0947 A0947 B0665 B0665 C0969 C0969
F0321 F0321 F0382 F0382 F0151 F0151
I0531 I0531 I0219 I0219 M0204 M0204
A0558 A0558 C2221 C2221 C0278 C0278
C2093 C2093 M0063 M0063 M1925 M1925
P0236 P0236 T0212 T0212 A0625 A0625
A0555 A0555 A0149 A0149 A0150 A0150
A0151 A0151 A0907 A0907 A2069 A2069
C0528 C0528 G0169 G0169 G0170 G0170
G0168 G0168 H0311 H0311 I0370 I0370
K0009 K0009 B1088 B1088 D3604 D3604
A2089 A2089 O0065 O0065 T0234 T0234
U0013 U0013 X0004 X0004
D1619 1,3-Dimethyl-6-chlorouracil
D2470 2,6-Dichloropurine
A1407 2-Amino-6-chloropurine
A1111 2-Aminopurine
F0647 2-Fluoroadenine
T0225 2-Thioxanthine
A0947 5-Aminoorotic Acid
B0665 5-Bromouracil
C0969 5-Chlorouracil
F0321 5-Fluorocytosine
F0382 5-Fluoroorotic Acid Monohydrate
F0151 5-Fluorouracil
I0531 5-Iodo-2,4-dimethoxypyrimidine
I0219 5-Iodouracil
M0204 5-Methylcytosine Hydrochloride
A0558 6-Azauracil
C2221 6-Chloro-2-fluoropurine
C0278 6-Chloropurine
C2093 6-Chlorouracil
M0063 6-Mercaptopurine Hydrate
M1925 6-Methoxypurine
P0236 6-Phenyl-2-thiouracil
T0212 6-Thioguanine
A0625 8-Azaguanine
A0555 8-Azahypoxanthine
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
H0311 Hypoxanthine
I0370 Isoguanine
K0009 Kinetin
B1088 N-6-Benzyladenine
D3604 N2,9-Diacetylguanine
A2089 N4-Acetylcytosine
O0065 Orotic Acid Monohydrate
T0234 Thymine
U0013 Uracil
X0004 Xanthine
Page Top

Phosphorylating Agents

C1215 C1215 C1250 C1250 C1210 C1210
C0976 C0976 C2228 C2228 B3125 B3125
C0977 C0977 C0978 C0978 D2624 D2624
D1059 D1059 M0905 M0905 M0904 M0904
P0209 P0209 P1223 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 [Phosphorylating Agent]
D2624 Dibenzyl N,N-Diisopropylphosphoramidite
D1059 Diphenyl Chlorophosphate
M0905 Methyl Dichlorophosphite [Phosphitylating Agent]
M0904 Methyl Phosphorodichloridate
P0209 Phenyl Dichlorophosphate
P1223 Tetrabenzyl Pyrophosphate
Page Top

Condensing Agents

T0340 T0340 T1410 T1410 N0604 N0604
T1985 T1985 T1562 T1562 T0459 T0459
M1186 M1186 M0071 M0071 N0477 N0477
M0625 M0625 D0436 D0436
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]
M0625 Mesitylenesulfonylimidazole
D0436 N,N'-Dicyclohexylcarbodiimide [for Peptide Synthesis]
Page Top

Protecting Agents for hydroxyl group

H0089 H0089 B1151 B1151 D1608 D1608
D2504 D2504 N0404 N0404 T1526 T1526
T1071 T1071 D1612 D1612 C0832 C0832
M0721 M0721 M0790 M0790 A0082 A0082
B0078 B0078 B0105 B0105 C0306 C0306
D2469 D2469 I0115 I0115 D1293 D1293
B0511 B0511 P0113 P0113 B0995 B0995
B1223 B1223 T0871 T0871 T0512 T0512
C0308 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]
D2504 2-Chlorophenyldiphenylmethyl 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
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 Triphenylmethyl Bromide
C0308 Triphenylmethyl Chloride
Page Top

Literature

1) J. D. Watson, F. H. C. Crick, Nature, 1953, 171, 737.
2) H. G. Khorana, Pure Appl. Chem., 1968, 17, 349.
3) R. L. Letsinger, K. K. Ogilvie, J. Am. Chem. Soc., 1967, 89, 4801.
4) R. L. Letsinger, W. B. Lundsford, J. Am. Chem. Soc., 1976, 98, 3655.
5) L. J. McBride, M. H. Caruthers, Tetrahedron Lett., 1983, 24, 245.
6) R. K. Saiki, T. L. Bugawan, G. T. Horn, K. B. Mullis, H. A. Erlich, Nature, 1986, 324, 163.

Page Top
kdjoad0000003wjb