Nucleosides, Nucleotides, Nucleic Acids and Related Reagents

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Genetic information is stored in DNA as combinatorial codes Nucleosides and Their Analogs held in nucleosides and nucleotides, in which form it is passed Nucleosides are glycosylamines made by attaching a from parents to their offspring. Analogs of nucleosides and nucleobase to a ribose or 2’-deoxyribose, which can be nucleotides are used clinically as medicinal agents such as phosphorylated producing nucleotides. Nucleoside analogs reverse transcriptase inhibitors. Therefore, the preparation and are an established class of clinically useful medicinal agents development of these species as effective, selective and possessing a wide range of antiviral and anticancer activities. nontoxic antiviral and antitumor agents has been the subject Consequently, extensive modifications have been made to of intense research.1) both the heterocyclic base and the sugar moiety. Some In addition to this, the development of Polymerase Chain representative examples of these are 9-[(2-hydroxyethoxy) Reaction (PCR) methodology has brought a dramatic change methyl]guanine (acyclovir) developed by Elion in 1977, which and rapid development in studies of DNA. At the current time shows antiviral activity; 3'-azido-3'-deoxythymidine (AZT) the draft version in decoding and mapping human genome discovered by Mitsuya et al. in 1985 and used for the treatment has been almost completed, and the functional analyses of of HIV infection; and cytosine β-D-arabinofuranoside genome and analyses of “Single Nucleotide Polymorphism” (cytarabine) approved by the FDA in 1969 and which has been (SNP) are being vigorously pursued. Discovery of the RNAi shown to display a range anticancer activities. In addition, process has facilitated the fast progression of studies of RNA. modified nucleosides such as 2’-deoxy-5-methylcytidine are At the same time, chemically synthesized oligoDNA and ubiquitous in living systems, and their functions have received oligoRNA have been studied as potential antisense DNAs, due attention from the scientific community.2) siRNAs and DNA aptamers, as oligonucleotide therapeutic Protected nucleosides, in which reactive amino and hydroxyl agents, primers for PCR method, and elements of DNA groups have been masked, e.g. N6-benzoyl-5'-O-(4,4'- computers. dimethoxytrityl)-2'-deoxyadenosine (Bz-DMT-dA), have been used for chemical synthesis of DNA and RNA.

Z0022 200mg 1g D3583 1g 5g

Nucleosides and Pyrimidine HO O N Their Analogs Nucleosides O OH OH Zebularine 2'-Deoxycytidine CAS RN: 3690-10-6 CAS RN: 951-77-9 D0048 5g 25g D0060 1g 5g 25g C0522 1g 5g 25g D3614 1g U0020 5g 25g

2'-Deoxycytidine Hydrochloride 2'-Deoxyuridine Cytidine 2'-Deoxy-2'-fluorocytidine Hydrate Uridine CAS RN: 3992-42-5 CAS RN: 951-78-0 CAS RN: 65-46-3 CAS RN: 10212-20-1 CAS RN: 58-96-8 P2396 50mg A0559 10mg M2290 1g 5g M2317 200mg 1g A2942 25mg 100mg O O O NH2

HN NH HN N HN

HO O HO O N HO O N HO O N O O O O

OH N OH OH OH OCH3 OH OCH3 3 Pseudouridine 6-Azauridine 2'-O-Methyluridine 2'-O-Methylcytidine 2'-Azido-2'-deoxyuridine CAS RN: 1445-07-4 CAS RN: 54-25-1 CAS RN: 2140-76-3 CAS RN: 2140-72-9 CAS RN: 26929-65-7

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D3615 1g 5g T2549 5g 25g A2232 20mg 100mg A2033 100mg 1g D3610 100mg 500mg 5g

NH2

N N

HO O N O

OH 2'-Deoxy-2'-fluorouridine 2',3',5'-Tri-O-acetyluridine 5-Aza-2'-deoxycytidine 5-Azacytidine 2'-Deoxy-5-methylcytidine CAS RN: 784-71-4 CAS RN: 4105-38-8 CAS RN: 2353-33-5 CAS RN: 320-67-2 CAS RN: 838-07-3 D3642 1g 5g D4220 50mg 200mg I0882 1g D3580 1g 5g F0635 5g 25g

NH2 NH2 CH2OH N I N HO O N HO O N O O

OH 2'-Deoxy-5-(hydroxymethyl)- OH 2'-Deoxy-5-fluorocytidine cytidine 5-Iodo-2'-deoxycytidine Stavudine Tegafur CAS RN: 10356-76-0 CAS RN: 7226-77-9 CAS RN: 611-53-0 CAS RN: 3056-17-5 CAS RN: 17902-23-7 B1575 1g 5g T0233 1g 5g 25g T2511 100mg 1g A2052 1g 5g D2235 100mg 500mg 1g

5-Bromo-2'-deoxyuridine Thymidine Trifluorothymidine Azidothymidine 2'-Deoxy-5-fluorouridine CAS RN: 59-14-3 CAS RN: 50-89-5 CAS RN: 70-00-8 CAS RN: 30516-87-1 CAS RN: 50-91-9 I0258 1g 5g 25g E1057 50mg 200mg E1093 50mg 200mg B0666 100mg 1g M1405 1g 5g 25g

O NH2 C CH C CH HN N

HO O N HO O N O O

OH OH Idoxuridine 5-Ethynyl-2'-deoxyuridine 5-Ethynyl-2'-deoxycytidine 5-Bromouridine 5-Methyluridine CAS RN: 54-42-2 CAS RN: 61135-33-9 CAS RN: 69075-47-4 CAS RN: 957-75-5 CAS RN: 1463-10-1 M1931 1g F0534 1g 5g D4342 1g 5g F0636 1g 5g D3579 1g 5g

NH2 F N

H3C O N O

OH OH 5-Methylcytidine 5-Fluorocytidine 5'-Deoxy-5-fluorocytidine 5-Fluorouridine 5'-Deoxy-5-fluorouridine CAS RN: 2140-61-6 CAS RN: 2341-22-2 CAS RN: 66335-38-4 CAS RN: 316-46-1 CAS RN: 3094-09-5 A2073 5g 25g A2356 1g 5g M3153 250mg 1g C2035 1g 5g D4200 10mg O O I HN HN

O N HO HO O N H3C F O O

1-(3,5-Anhydro-2-deoxy-β-D- OH OH OH threo-pentofuranosyl)thymine 1-β-D-Arabinofuranosyluracil 2'-C-Methyluridine Cytarabine Fialuridine CAS RN: 7481-90-5 CAS RN: 3083-77-0 CAS RN: 31448-54-1 CAS RN: 147-94-4 CAS RN: 69123-98-4 G0367 100mg 1g D4823 200mg 1g C2208 5g 25g C2207 1g 5g A2431 1g O

HO O N H3C O

OH F (2'R)-2'-Deoxy-2'-fluoro- 2,2'-O-Anhydro- Gemcitabine Hydrochloride 2'-methyluridine 2,2'-O-Cyclouridine 2,2'-O-Cyclocytidine Hydrochloride 5-methyluridine CAS RN: 122111- 03-9 CAS RN: 863329-66-2 CAS RN: 3736-77-4 CAS RN: 10212-25-6 CAS RN: 22423-26-3 R0077 100mg 500mg A2528 50mg M2399 50mg 250mg B3094 1g 5g B3102 100mg 1g O O NH C NH2 C 2 N N

HO N NH2 HO N OH O O

OH OH OH OH Ribavirin Acadesine Mizoribine N4-Benzoylcytidine N4-Benzoyl-2'-deoxycytidine CAS RN: 36791-04-5 CAS RN: 2627-69-2 CAS RN: 50924-49-7 CAS RN: 13089-48-0 CAS RN: 4836-13-9

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B3404 100mg B3631 1g 5g L0217 100mg 1g C0525 100mg 1g C2878 1g 5g O NH C O(CH2)4CH3 F N

H3C O N O N4-Benzoyl-3',5'-O- (1,1,3,3-tetraisopropyl-1,3- OH OH Brivudine disiloxanediyl)cytidine Lamivudine Cytidine Sulfate Capecitabine CAS RN: 69304-47-8 CAS RN: 69304-43-4 CAS RN: 134678-17-4 CAS RN: 32747-18-5 CAS RN: 154361-50-9 D3566 5g 25g B3087 1g 5g F0842 500mg 5g H1290 5g 25g

N N Purine O H2N N N CH2O C CH3 CH2CH2CH Nucleosides CH2O C CH3 5'-O-(4,4'-Dimethoxytrityl)- N4-Benzoyl-5'-O-(4,4'- O thymidine dimethoxytrityl)-2'-deoxycytidine Famciclovir 9-(2-Hydroxyethyl)adenine CAS RN: 40615-39-2 CAS RN: 67219-55-0 CAS RN: 104227-87-4 CAS RN: 707-99-3 H1291 1g 5g E0899 50mg 200mg A1915 1g 5g 25g P2164 200mg 1g G0315 5g 25g O NH2 O O HN N N N . H O HN N HN N . H N N N 2 xH2O N N 2 CH 2 H2N N N H2N N N CH3 CH2OH CH2OH CH CH CH 2 2 CH2OCH CH OH CH2OH 2 OH HO CH2OH (R)-9-(2-Hydroxypropyl)adenine Entecavir Monohydrate Acyclovir Penciclovir Ganciclovir Hydrate CAS RN: 14047-28-0 CAS RN: 209216-23-9 CAS RN: 59277-89-3 CAS RN: 39809-25-1 CAS RN: 82410-32-0 A3228 1g D4256 1g 5g A2414 100mg 1g V0111 100mg 1g D3065 100mg

NH2

O N N O CH N 3 O HN O N N O N OCH2CH3 CH3 N N H CH2CH2OCH2 P O CH3 OCH CH O 2 3 O Diethyl [[2-(6-Amino-9H-purin- Valacyclovir Hydrochloride Triacetylganciclovir 9-yl)ethoxy]methyl]phosphonate Adefovir Dipivoxil Hydrate 2',3'-Dideoxyadenosine CAS RN: 86357-14-4 CAS RN: 116384-53-3 CAS RN: 142340-99-6 CAS RN: 124832-27-5 CAS RN: 4097-22-7 D3066 100mg 500mg D0046 5g 25g C2815 25mg 100mg D4137 5g D3584 1g 5g

NH2

N N

HO N N O . xH2O OH Didanosine 2'-Deoxyadenosine Monohydrate Cordycepin Hydrate 2'-Deoxyadenosine Anhydrous 2'-Deoxyinosine CAS RN: 69655-05-6 CAS RN: 16373-93-6 CAS RN: 73-03-0 CAS RN: 958-09-8 CAS RN: 890-38-0 D4292 100mg 1g C2499 50mg B4001 200mg 1g D0052 1g 5g 25g N1144 25mg 100mg

Cl NH O OCH3 N 2 N N N N NH N HO N Cl HO N O HO N N Cl HO Br N N NH2 HO N NH2 O O O OH OH OH 5,6-Dichlorobenzimidazole OH OH 1-β-D-Ribofuranoside Cladribine 8-Bromo-2'-deoxyguanosine 2'-Deoxyguanosine Hydrate Nelarabine CAS RN: 53-85-0 CAS RN: 4291-63-8 CAS RN: 13389-03-2 CAS RN: 961-07-9 CAS RN: 121032-29-9 C2206 1g 5g A0152 5g 25g 100g M2291 1g I0037 25g 500g B3460 100mg 1g

NH2

N N

HO N N O

6 OH OCH3 N -Dibenzoyladenosine 6-Chloropurine Riboside Adenosine 2'-O-Methyladenosine Inosine 2',3'-Dibenzoate CAS RN: 5399-87-1 CAS RN: 58-61-7 CAS RN: 2140-79-6 CAS RN: 58-63-9 CAS RN: 58463-04-0 F0656 200mg 1g T2690 1g T2691 1g 5g T2692 1g 5g B4002 1g 5g O

N NH

HO Br N N NH2 O

. xH2O 2',3',5'-Tri-O-acetyl-2-amino- 2',3',5'-Tri-O-acetyl-6-chloro- OH OH 2-Fluoroadenosine 6-chloropurine Riboside 2-iodopurine Riboside 2',3',5'-Tri-O-acetylguanosine 8-Bromoguanosine Hydrate CAS RN: 146-78-1 CAS RN: 16321-99-6 CAS RN: 5987-76-8 CAS RN: 6979-94-8 CAS RN: 4016-63-1

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A2054 1g 5g C2192 100mg 1g A2135 5g 25g G0171 5g 25g 100g M2318 200mg 1g O

N NH

HO N N NH2 O

. xH2O OH OCH3 2-Amino-6-chloropurine Riboside 2-Chloroadenosine Hydrate 2-Aminoadenosine Guanosine 2'-O-Methylguanosine Hydrate CAS RN: 2004-07-1 CAS RN: 146-77-0 CAS RN: 2096-10-8 CAS RN: 118-00-3 CAS RN: 2140-71-8 X0008 100mg I0759 200mg 1g 5g C2500 20mg 100mg V0098 1g 5g A2739 10mg 50mg O

N NH

HO N N NH HO 2 O

. xH O OH 2 9-β-D-Arabinofuranosylguanine Xanthosine Dihydrate 2-Iodoadenosine Clofarabine Vidarabine Monohydrate Hydrate CAS RN: 146-80-5 CAS RN: 35109-88-7 CAS RN: 123318-82-1 CAS RN: 24356-66-9 CAS RN: 38819-10-2 O0401 200mg 1g I0700 100mg 1g I0699 100mg 1g I0702 5g 25g I0704 5g

NH2

HN N

HO O N N O

OH OH 8-Oxoadenosine N2-Isobutyryl-2'-deoxyguanosine N2-Isobutyrylguanosine Monohydrate 2',3'-O-Isopropylideneadenosine 2',3'-O-Isopropylideneinosine CAS RN: 29851-57-8 CAS RN: 68892-42-2 CAS RN: 64350-24-9 CAS RN: 362-75-4 CAS RN: 2140-11-6 I0703 5g B3093 1g 5g B3101 100mg 1g D4228 25mg P2311 25mg

O CH3 CH3 N HN CH3 N N N N HO N N O N N O O CH3O NH2 NH OH O P O O CH3 6 ONa . 2HCl N -Benzoyl-2'- O O 2',3'-O-Isopropylideneguanosine N6-Benzoyladenosine Hydrate deoxyadenosine Hydrate Dibutyryl cAMP Sodium Salt Puromycin Dihydrochloride CAS RN: 362-76-5 CAS RN: 4546-55-8 CAS RN: 206752-42-3 CAS RN: 16980-89-5 CAS RN: 58-58-2 B3103 100mg 1g I0697 1g 5g

N6-Benzoyl-5'-O-(4,4'- N2-Isobutyryl-5'-O-(4,4'- dimethoxytrityl)-2'-deoxyadenosine dimethoxytrityl)-2'-deoxyguanosine CAS RN: 64325-78-6 CAS RN: 68892-41-1

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

C0524 1g 5g C1675 1g 5g

Nucleotides and Pyrimidine Their Analogs Nucleotides Cytidine 5'-Monophosphate Disodium Salt Hydrate Cytidine 5'-Monophosphate CAS RN: 6757-06-8 CAS RN: 63-37-6

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D3673 100mg 1g T0845 100mg U0021 5g 25g C0523 10mg 100mg 1g U0022 100mg

2'-Deoxycytidine Thymidine 5'-Monophosphate Uridine 5'-Monophosphate Cytidine 5'-Diphosphate Uridine 5'-Triphosphate 5'-Monophosphate Hydrate Disodium Salt Hydrate Disodium Salt Hydrate Trisodium Salt Hydrate Trisodium Salt Hydrate CAS RN: 1032-65-1 CAS RN: 33430-62-5 CAS RN: 3387-36-8 CAS RN: 34393-59-4 CAS RN: 19817-92-6 A0158 1g 5g 25g I0036 1g 5g 25g A0626 100mg 1g A0157 1g 5g 25g

Purine Nucleotides Inosine 5'-Monophosphate Adenosine 5'-Diphosphate Adenosine 5'-Triphosphate 5'-Adenylic Acid Disodium Salt Hydrate Disodium Salt Hydrate Disodium Salt Hydrate CAS RN: 61-19-8 CAS RN: 4691-65-0 CAS RN: 16178-48-6 CAS RN: 34369-07-8 A2112 100mg 1g A2381 1g 5g I0039 100mg F0913 25mg 100mg G0172 25g 100g

NH2

N N O HO P O N N F HO OH O

Adenosine 3',5'-Cyclic Adenosine 3',5'-Cyclic Inosine 5'-Monophosphate OH Guanosine 5'-Monophosphate Monophosphate Sodium Salt Hydrate Monophosphate Hydrate Barium Salt Hydrate Fludarabine Monophosphate Disodium Salt Hydrate CAS RN: 37839-81-9 CAS RN: 60-92-4 CAS RN: 3249-92-1 CAS RN: 75607-67-9 CAS RN: 5550-12-9 I0038 100mg

Inosine 5'-Triphosphate Trisodium Salt Hydrate CAS RN: 35908-31-7 D3545 5g 25g R0022 25g R0024 25g Deoxyribonucleic Acid Ribonucleic Acid Ribonucleic Acid Sodium Sodium Salt from Salmon Milt from Yeast Salt from Yeast CAS RN: 9007-49-2 Nucleic Acids

D0920 100mg 1g 5g N0943 100mg C0379 100mg 1g β-NADH Disodium Salt β-NADP β-NADP Sodium Salt Hydrate, reduced form Hydrate, oxidized form Enzymes and Coenzymes CAS RN: 606-68-8 CAS RN: 53-59-8 CAS RN: 1184-16-3 related to Nucleic Acids P0251 100mg D0919 1g 5g T0521 100mg Phosphatase, Acid from β-NAD Hydrate, oxidized β-NADPH Tetrasodium Wheat Germ form Salt reduced form CAS RN: 9001-77-8 CAS RN: 53-84-9 CAS RN: 2646-71-1 T2980 100mg T2979 100mg Thionicotinamide Adenine Thionicotinamide Adenine Dinucleotide Disodium Dinucleotide oxidized form Salt reduced form CAS RN: 4090-29-3

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Nucleobases and Their Analogs of these basic structures. For example, hypoxanthine and Nucleobases, usually simply called “bases”, are a vital sense xanthine are generated in living systems through deamination component of DNA and RNA. The bases can be divided into of adenine and guanine, respectively. Furthermore, nucleobase two groups based on the structure: purines such as adenine analogue 5-fluorouracil (5-FU) is used as an anticancer agent. and guanine; and pyrimidines such as cytosine, thymine and Derivatives of 2-fluoroadenine have been widely reported as uracil. Other nucleobases can be created by the modification prodrug forms of anticancer agents.

M2355 1g 5g C0528 5g 25g 100g

Nucleobases and Pyrimidine N

Their Analogs Nucleobases N SCH3 2-Methylthio-4-pyrimidinol Cytosine CAS RN: 5751-20-2 CAS RN: 71-30-7 I0814 5g T2757 1g U0013 25g 100g 500g T0224 25g 250g A2089 5g 25g

O O

N NH

N NH2 N S H H Isocytosine 4-Thiouracil Uracil 2-Thiouracil N4-Acetylcytosine CAS RN: 108-53-2 CAS RN: 591-28-6 CAS RN: 66-22-8 CAS RN: 141-90-2 CAS RN: 14631-20-0 B3169 5g A0558 1g 5g A2136 1g 5g I0531 1g 5g A2125 5g

4-Amino-5-fluoro- N4-Benzoylcytosine 6-Azauracil 4-Amino-6-chloropyrimidine 5-Iodo-2,4-dimethoxypyrimidine 2-methoxypyrimidine CAS RN: 26661-13-2 CAS RN: 461-89-2 CAS RN: 5305-59-9 CAS RN: 52522-99-3 CAS RN: 1993-63-1 B0665 25g T1622 1g 5g C0969 5g 25g M0204 100mg 1g 5g T0234 5g 25g 100g

5-Bromouracil 5-(Trifluoromethyl)uracil 5-Chlorouracil 5-Methylcytosine Hydrochloride Thymine CAS RN: 51-20-7 CAS RN: 54-20-6 CAS RN: 1820-81-1 CAS RN: 58366-64-6 CAS RN: 65-71-4 M0994 10g 25g F0151 5g 25g F0321 1g 5g 25g A0898 5g 25g I0219 5g 25g

H2N NH

N O H 5-Methyl-2-thiouracil 5-Fluorouracil 5-Fluorocytosine 5-Aminouracil 5-Iodouracil CAS RN: 636-26-0 CAS RN: 51-21-8 CAS RN: 2022-85-7 CAS RN: 932-52-5 CAS RN: 696-07-1 N0281 5g 25g E0807 1g 5g E1096 200mg 1g A2670 1g 5g C2093 5g 25g

O O O O CH C O2N HC C 3 NH NH NH

N O N O N O H H H 5-Nitrouracil 5-Ethyluracil 5-Ethynyluracil 5-Acetyluracil 6-Chlorouracil CAS RN: 611-08-5 CAS RN: 4212-49-1 CAS RN: 59989-18-3 CAS RN: 6214-65-9 CAS RN: 4270-27-3 M0454 25g 500g M0443 25g 500g A0658 25g 250g C1057 5g 25g A2449 5g 25g

O O O O O

NH NH NH NH NH

CH3 N O CH3 N S H2N N O ClCH2 N O H2N N O H H H H CH3 6-Methyluracil 6-Methyl-2-thiouracil 6-Aminouracil 6-Chloromethyluracil 6-Amino-1-methyluracil CAS RN: 626-48-2 CAS RN: 56-04-2 CAS RN: 873-83-6 CAS RN: 18592-13-7 CAS RN: 2434-53-9

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P0533 25g O0065 25g 100g 500g P0236 1g 5g C2300 5g 25g M2506 1g 5g

O O

O2N NH NH

CH3CH2CH2 N S CH3 N O H H 6-Propyl-2-thiouracil Orotic Acid Monohydrate 6-Phenyl-2-thiouracil 6-Chloro-3-methyluracil 6-Methyl-5-nitrouracil CAS RN: 51-52-5 CAS RN: 50887-69-9 CAS RN: 36822-11-4 CAS RN: 4318-56-3 CAS RN: 16632-21-6 D1136 1g 5g F0382 100mg 1g A0947 25g D4324 1g

O O

CH3 NH Purine HN

CH3 N O N N H Nucleobases H 5,6-Dimethyluracil 5-Fluoroorotic Acid Monohydrate 5-Aminoorotic Acid 7-Deazahypoxanthine CAS RN: 26305-13-5 CAS RN: 703-95-7 CAS RN: 7164-43-4 CAS RN: 3680-71-5 C2306 1g 5g A0907 25g 250g A1041 100mg 1g 5g C0278 5g 25g H0311 5g 25g

NH2

N N N N H 6-Chloro-7-deazapurine Allopurinol 4-Aminopyrazolo[3,4-d]pyrimidine 6-Chloropurine Hypoxanthine CAS RN: 3680-69-1 CAS RN: 315-30-0 CAS RN: 2380-63-4 CAS RN: 87-42-3 CAS RN: 68-94-0 A0149 25g 250g M1925 1g 5g M0063 1g 5g A0150 5g 25g A0151 25g 100g

Adenine 6-Methoxypurine 6-Mercaptopurine Monohydrate Adenine Hydrochloride Hemihydrate Adenine Sulfate Dihydrate CAS RN: 73-24-5 CAS RN: 1074-89-1 CAS RN: 6112-76-1 CAS RN: 2922-28-3 CAS RN: 6509-19-9 D3894 1g 5g B3355 5g 25g B1088 5g 25g K0009 1g 5g B3344 5g 25g

6-(Dimethylamino)purine 6-Benzyloxypurine N6-Benzyladenine Kinetin N6-Benzoyladenine CAS RN: 938-55-6 CAS RN: 57500-07-9 CAS RN: 1214-39-7 CAS RN: 525-79-1 CAS RN: 4005-49-6 A0555 1g A2069 5g 25g A1111 200mg 1g M2518 200mg 1g H1290 5g 25g

NH2

N N

CH3 8-Azahypoxanthine Azathioprine 2-Aminopurine 3-Methyladenine 9-(2-Hydroxyethyl)adenine CAS RN: 2683-90-1 CAS RN: 446-86-6 CAS RN: 452-06-2 CAS RN: 5142-23-4 CAS RN: 707-99-3 C2845 200mg 1g C3130 1g 5g I0941 1g 5g D4284 1g 5g A2699 100mg Cl

NH2 N N Cl Cl NH2 I N N I N N N N N O N N N N N H Cl N N O N N H H H H 6-Chloro-9-(tetrahydropyran- 3-Iodo-1H-pyrazolo- 2-yl)purine 6-Chloro-7-iodo-7-deazapurine [3,4-d]pyrimidin-4-amine 2,6-Dichloro-7-deazapurine AHPP CAS RN: 7306-68-5 CAS RN: 123148-78-7 CAS RN: 151266-23-8 CAS RN: 90213-66-4 CAS RN: 5472-41-3 I0370 100mg F0647 200mg 1g G0169 1g 25g 250g T0212 1g 5g T0225 1g 5g

Isoguanine 2-Fluoroadenine Guanine 6-Thioguanine 2-Thioxanthine CAS RN: 3373-53-3 CAS RN: 700-49-2 CAS RN: 73-40-5 CAS RN: 154-42-7 CAS RN: 2487-40-3

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X0004 25g G0170 25g G0168 1g 25g D2470 1g 5g 25g C2221 1g

Xanthine Guanine Hydrochloride Hydrate Guanine Sulfate Dihydrate 2,6-Dichloropurine 6-Chloro-2-fluoropurine CAS RN: 69-89-6 CAS RN: 635-39-2 CAS RN: 10333-92-3 CAS RN: 5451-40-1 CAS RN: 1651-29-2 C2575 1g 5g D1625 5g 25g A1407 1g 5g A2068 5g 25g A1248 1g 5g

2-Chloroadenine 2,6-Diaminopurine Monohydrate 2-Amino-6-chloropurine 2-Amino-6-iodopurine 2-Acetamido-6hydroxypurine CAS RN: 1839-18-5 CAS RN: 1904-98-9 CAS RN: 10310-21-1 CAS RN: 19690-23-4 CAS RN: 19962-37-9 N0958 20mg 100mg D4295 1g 5g D3604 25g M2073 5g 25g M2432 50mg 200mg

OCH2 O Cl CH3 N N N N N . HCl H2N NN Cl N O N N H H H H 5,6-Dichlorobenzimidazole NU 2058 Hydrochloride N2,9-Diacetylguanine 3-Methylxanthine 1-Methylxanthine CAS RN: 161058-83-9 CAS RN: 1087737-96-9 CAS RN: 3056-33-5 CAS RN: 1076-22-8 CAS RN: 6136-37-4 A2805 25g 100g B4134 1g B4454 200mg 1g B3456 1g 5g C0293 25g 250g

O O O CH2 C C CH3 CH3 HN N N N HN N H2N NH2 O N N O N N Br H CH O N N Br 3 2 H CH3 CH3 8-Bromo-7-(2-butyn-1-yl)- Aminophylline 8-Bromo-3-methylxanthine 3-methylxanthine 8-Bromotheophylline 8-Chlorotheophylline CAS RN: 317-34-0 CAS RN: 93703-24-3 CAS RN: 666816-98-4 CAS RN: 10381-75-6 CAS RN: 85-18-7 D5146 1g 5g

Cl N

Cl N H

5,6-Dichlorobenzimidazol CAS RN: 6478-73-5

Pharmacologically-Active Nucleosides and Nucleobases research are shown below, and serve as important cofactors in for Research and Experimental Use metabolism. Typical nucleosides and nucleobases used in pharmacology

F0151 5g 25g F0321 1g 5g 25g R0077 100mg 500mg Pharmacologically-Active Nucleosides and Nucleobases for Research and 5-Fluorouracil 5-Fluorocytosine Ribavirin Experimental Use CAS RN: 51-21-8 CAS RN: 2022-85-7 CAS RN: 36791-04-5

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M2399 50mg 250mg A2528 50mg L0217 100mg 1g A2232 20mg 100mg C2035 1g 5g

O O NH2

C NH2 C NH2 N N N N

HO N OH HO N NH2 HO O N O O O

OH OH OH OH OH Mizoribine Acadesine Lamivudine Decitabine Cytarabine CAS RN: 50924-49-7 CAS RN: 2627-69-2 CAS RN: 134678-17-4 CAS RN: 2353-33-5 CAS RN: 147-94-4 A2033 100mg 1g D4823 200mg 1g G0367 100mg 1g F0635 5g 25g D3580 1g 5g O

HO O N H3C O

OH F 5-Azacytidine PSI-6206 Gemcitabine Hydrochloride Tegafur Stavudine CAS RN: 320-67-2 CAS RN: 863329-66-2 CAS RN: 122111- 03-9 CAS RN: 17902-23-7 CAS RN: 3056-17-5 A2052 1g 5g B1575 1g 5g T2511 100mg 1g D2235 100mg 500mg 1g I0258 1g 5g 25g

Azidothymidine 5-Bromo-2'-deoxyuridine Trifluorothymidine 2'-Deoxy-5-fluorouridine Idoxuridine CAS RN: 30516-87-1 CAS RN: 59-14-3 CAS RN: 70-00-8 CAS RN: 50-91-9 CAS RN: 54-42-2 B3404 100mg D3579 1g 5g F0636 1g 5g D4342 1g 5g C2878 1g 5g

NH2 O NH C O(CH ) CH F 2 4 3 N F N

H3C O N H C O N O 3 O

OH OH OH OH Brivudine Doxifluridine 5-Fluorouridine 5'-Deoxy-5-fluorocytidine Capecitabine CAS RN: 69304-47-8 CAS RN: 3094-09-5 CAS RN: 316-46-1 CAS RN: 66335-38-4 CAS RN: 154361-50-9 A0907 25g 250g M0063 1g 5g K0009 1g 5g A2069 5g 25g A2737 200mg 1g

NH2

N N N N

Allopurinol 6-Mercaptopurine Monohydrate Kinetin Azathioprine PP 3 CAS RN: 315-30-0 CAS RN: 6112-76-1 CAS RN: 525-79-1 CAS RN: 446-86-6 CAS RN: 5334-30-5 A2414 100mg 1g D3066 100mg 500mg D3065 100mg V0098 1g 5g C2689 25mg

NH2

N N

HO N N O

Cordycepin OH Adefovir Dipivoxil Didanosine 2',3'-Dideoxyadenosine Vidarabine Monohydrate from Cordyceps militaris CAS RN: 142340-99-6 CAS RN: 69655-05-6 CAS RN: 4097-22-7 CAS RN: 24356-66-9 CAS RN: 73-03-0 C2815 25mg 100mg D4228 25mg P2311 25mg D4292 100mg 1g H1542 1g 5g

O O CH3 CH3 O NH2 H2N N CH3CH3 O NH CH3 2 HN CH3 Cl O N N N H2N N N N N CH 3 Co NH N N H 2 O N O CH N CH 3 HO N N 3 HO N N O N N HO N Cl H2N CH3 O CH3 CH3 O O O CH3O O NH2 NH O CH3 O 2 NH N NH OH O . O P O O CH3 CH O P O HON CH3 xH2O 3 ONa . O 2HCl OH OH O OH O O HO Cordycepin Hydrate Dibutyryl cAMP Sodium Salt Puromycin Dihydrochloride DRB Hydroxocobalamin Acetate CAS RN: 73-03-0 CAS RN: 16980-89-5 CAS RN: 58-58-2 CAS RN: 53-85-0 CAS RN: 22465-48-1 M2742 1g C2499 50mg C2500 20mg 100mg F0913 25mg 100mg A2739 10mg 50mg O H N O O 2 CH NH2 NH2 CH3 3 O CH NH2 3 O H N 2 N CH3 N N N N N N NH CH3 Co NH H 2 O N N O CH3 H2N CH3 HO N N Cl HO N N NH CH CH3 HO P O N N F 2 O 3 HO NH2 HO O CH3 O NH N O OH O O N CH3 CH3 O P O HO O . . xH2O O xH2O OH HO OH OH Methylcobalamin Hydrate Cladribine Clofarabine Fludarabine Monophosphate Ara-G Hydrate CAS RN: 288315-09-3 CAS RN: 4291-63-8 CAS RN: 123318-82-1 CAS RN: 75607-67-9 CAS RN: 38819-10-2

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F0842 500mg 5g A2699 100mg T0212 1g 5g N0958 20mg 100mg T2744 500mg 5g

NH2 OCH2 N N O N N N H2N N N CH2O C CH3 N CH2CH2CH CH2O C CH3 O N N H N NN H H 2 O H Famciclovir AHPP 6-Thioguanine NU 2058 Temozolomide CAS RN: 104227-87-4 CAS RN: 5472-41-3 CAS RN: 154-42-7 CAS RN: 161058-83-9 CAS RN: 85622-93-1 A1915 1g 5g 25g P2164 200mg 1g G0315 5g 25g E0899 50mg 200mg V0111 100mg 1g O O O HN N . . H2O HN N HN N xH2O H2N N N

CH2 H2N N N H2N N N CH2OH CH OH CH CH CH 2 2 2 CH2OCH CH2OH CH2OH HO CH2OH Acyclovir Penciclovir Ganciclovir Hydrate Entecavir Monohydrate Valacyclovir Hydrochloride Hydrate CAS RN: 59277-89-3 CAS RN: 39809-25-1 CAS RN: 82410-32-0 CAS RN: 209216-23-9 CAS RN: 124832-27-5 V0158 250mg 1g A2694 1g 5g T0179 25g 100g 500g A2805 25g 100g H0402 25g 500g

NH CH O O 3

N . HCl N N CH3 O N N N N N H2N OH NH N NH H2N N N 2 H2N N 2 O N N N H H O CH3 CH3 N O CH3 2

O CH3 HO O CH2CH2OH Valganciclovir Hydrochloride Abacavir Theophylline Aminophylline Etofylline CAS RN: 175865-59-5 CAS RN: 136470-78-5 CAS RN: 58-55-9 CAS RN: 317-34-0 CAS RN: 519-37-9 C2042 25g 500g C2748 5g 25g H1430 5g 25g D3600 25g 500g T2941 25g

O O O O O OH O OH CH CH CH CH CH CH C OH CH3 CH3 CH3 CH2CH2Cl 3 2 3 CH3 CH2 CH CH2OH 3 2 N N N N N N N N N N

O N N O NN O N N O NN O N N CH3 CH 3 CH3 CH3 CH3 Caffeine 7-(2-Chloroethyl)theophylline Proxyphylline Diprophylline Theophylline-7-acetic Acid CAS RN: 58-08-2 CAS RN: 5878-61-5 CAS RN: 603-00-9 CAS RN: 479-18-5 CAS RN: 652-37-9 D4302 1g 25g

CH3 N N O O O N N

CH3 Doxofylline CAS RN: 69975-86-6

The dicyclohexylcarbodiimide (DCC) method exemplified by the Nucleic Acid Synthesis Agents Khorana group, the phosphotriester method and phosphitetriester Silylation converts insoluble nucleobases into lipophilic method by the team of Letsinger and the phosphoramidite method trimethylsilyled derivatives, which are readily soluble in organic by the Caruthers group are examples of the various synthetic solvents, permitting homogenous chemical reactions. The methods. Recently, the phosphoramidite method has been used trimethylsilylated nucleobases react with protected sugars to frequently in tandem with the penetration of DNA synthesizers, thus afford nucleosides. The procedure is commonly referred to as 2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite has been the Hilbert-Johnson reaction modified by Vorbrüggen et al. the reagent of frequent choice for the phosphitylation due to its ease Phosphorylating and phosphorothioating agents, condensing in handling and safety.3) 1,2,4-Triazole and 1H-tetrazole are also used agents and protecting agents for hydroxy and amino groups are of for chemical conversion of uridines into cytidines. importance in the synthesis of DNA and RNA chains. Active research Chemically synthesized DNA is becoming important as a on chemical synthesis of DNA and RNA is being conducted, and a primer for the PCR method, an antisense molecule, or an variety of synthetic methods using these agents are being developed. element of the DNA computer.

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A0082 100g 500g I0115 25g 100g 500g Protecting Nucleic Acid Synthesis Agents for Agents Hydroxy and Amino Groups Acetyl Chloride Isobutyryl Chloride CAS RN: 75-36-5 CAS RN: 79-30-1 P0677 25mL 500mL C0306 25mL 100mL 500mL D1293 25mL 100mL 500mL B0995 5g 25g 100g D2334 5g 25g

N,N-Dimethylformamide 1,3-Dichloro-1,1,3,3- Pivaloyl Chloride Chlorotrimethylsilane Dimethyl Acetal TBSCl tetramethyldisiloxane CAS RN: 3282-30-2 CAS RN: 75-77-4 CAS RN: 4637-24-5 CAS RN: 18162-48-6 CAS RN: 2401-73-2 H0089 10mL 25mL 100mL 500mL T0871 5g 25g 250g D1608 5g 25g D2469 5g D3135 1g 5g

Trimethylsilyl 1,3-Dichloro-1,1,3,3- Di-tert-butylsilyl HMDS Trifluoromethanesulfonate tetraisopropyldisiloxane Di-tert-butyldichlorosilane Bis(trifluoromethanesulfonate) CAS RN: 999-97-3 CAS RN: 27607-77-8 CAS RN: 69304-37-6 CAS RN: 18395-90-9 CAS RN: 85272-31-7 B0511 10mL 100mL P0113 25g 500g B0105 25mL 500mL M0721 25g 100g 500g N0404 5g 25g

BSA Phenoxyacetyl Chloride Benzoyl Chloride 4-Methoxybenzoyl Chloride 2-Nitrobenzyl Bromide CAS RN: 10416-59-8 CAS RN: 701-99-5 CAS RN: 98-88-4 CAS RN: 100-07-2 CAS RN: 3958-60-9 T0459 25g 500g B1151 5g C0832 25g 100g 500g B0078 25g 100g 500g T1071 5g 25g

2,4,6-Triisopropylbenzene- 1,3-Benzodithiolylium sulfonyl Chloride Tetrafluoroborate 4-Chlorophenoxyacetyl Chloride Benzoic Anhydride 4,4',4''-Tris(benzoyloxy)trityl Bromide CAS RN: 6553-96-4 CAS RN: 57842-27-0 CAS RN: 4122-68-3 CAS RN: 93-97-0 CAS RN: 86610-66-4 B1223 5mL 25mL 100mL C0308 25g 100g 500g T0512 25g 100g D2504 25g M0790 25g 250g

tert-Butyldiphenyl- chlorosilane Trityl Chloride Trityl Bromide 2-Chlorotrityl Chloride 4-Methoxytrityl Chloride CAS RN: 58479-61-1 CAS RN: 76-83-5 CAS RN: 596-43-0 CAS RN: 42074-68-0 CAS RN: 14470-28-1 D1612 5g 25g T1526 1g M0905 10g M0904 5g 25g 100g Phosphorylating and Phosphorothioating 4,4',4''-Tris(4,5-dichloro- 4,4'-Dimethoxytrityl Chloride phthalimido)trityl Bromide Agents Methyl Dichlorophosphite Methyl Phosphorodichloridate CAS RN: 40615-36-9 CAS RN: 91898-93-0 CAS RN: 3279-26-3 CAS RN: 677-24-7 D0764 25g T1895 25g D0624 25g 500g C0978 5g 25g D2883 25g

S Cl P Cl Cl Barium 2-Cyanoethylphosphate Dimethyl Chlorothiophosphate Thiophosphoryl Chloride Diethyl Chlorothiophosphate Hydrate Diphosphoryl Chloride CAS RN: 2524-03-0 CAS RN: 3982-91-0 CAS RN: 2524-04-1 CAS RN: 5015-38-3 CAS RN: 13498-14-1

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B5440 200mg 1g C2228 1g 5g D4211 1g 5g C1215 5g 25g C1250 5g 25g

O O CH3 CH3 O P O P O CH3 N CH3 OH OH P (CH3)3CO OC(CH3)3 2 (C4H9)4N Bis(tetrabutylammonium) 2-Cyanoethyl N,N,N',N'- Di-tert-butyl N,N- 2-Chloro-1,3,2-dioxa- 2-Chloro-2-oxo- Dihydrogen Pyrophosphate Tetraisopropylphosphordiamidite Diisopropylphosphoramidite phospholane 1,3,2-dioxaphospholane CAS RN: 857447-79-1 CAS RN: 102691-36-1 CAS RN: 137348-86-8 CAS RN: 822-39-9 CAS RN: 6609-64-9 P0209 25g 500g C0977 5g 25g C0976 5g 25g C1210 5g 25g C3326 200mg 1g

Cl O CH3 P O N CH3

CH3 CH3 4-Chlorophenyl 2-Chlorophenyl 2-Chloro-4H-1,3,2- 5-Chlorosaligenyl-N,N- Phenyl Dichlorophosphate Phosphorodichloridate Phosphorodichloridate benzodioxaphosphorin-4-one diisopropylphosphoramidite CAS RN: 770-12-7 CAS RN: 772-79-2 CAS RN: 15074-54-1 CAS RN: 5381-99-7 CAS RN: 1620086-77-2 B3125 1g 5g D1059 25g 100g 500g P1223 1g B3623 5g 25g D2624 5g

O S S O 3H-1,2-Benzodithiol-3-one Dibenzyl N,N-Diisopropyl- 1,1-Dioxide Diphenyl Chlorophosphate Tetrabenzyl Pyrophosphate Bis(phenylacetyl) Disulfide phosphoramidite CAS RN: 66304-01-6 CAS RN: 2524-64-3 CAS RN: 990-91-0 CAS RN: 15088-78-5 CAS RN: 108549-23-1 P0677 25mL 500mL T0340 25g 100g 500g T1017 5g 25g T1985 5g 25g

Condensing Agents 1-(p-Toluenesulfonyl)- Pivaloyl Chloride 1,2,4-Triazole 1H-Tetrazole imidazole CAS RN: 3282-30-2 CAS RN: 288-88-0 CAS RN: 288-94-8 CAS RN: 2232-08-8 N0477 1g 5g E0670 1g 5g B3020 25g D2026 25g 250g C2325 5g 25g

3-Nitro-1,2,4-triazole 5-(Ethylthio)-1H-tetrazole 5-(Benzylthio)-1H-tetrazole 4,5-Dicyanoimidazole 1,1'-Carbonyldi(1,2,4-triazole) CAS RN: 24807-55-4 CAS RN: 89797-68-2 CAS RN: 21871-47-6 CAS RN: 1122-28-7 CAS RN: 41864-22-6 D0436 25g 400g D3792 5g 25g C2421 5g M0071 25g 100g 500g T0459 25g 500g

N,N'-Dicyclohexylcarbodiimide N,N'-Dicyclohexyl-4- 1-(Cyanomethyl)- 2,4,6-Triisopropylbenzene- (= DCC) morpholinecarboxamidine piperidinium Tetrafluoroborate 2-Mesitylenesulfonyl Chloride sulfonyl Chloride CAS RN: 538-75-0 CAS RN: 4975-73-9 CAS RN: 434937-12-9 CAS RN: 773-64-8 CAS RN: 6553-96-4 T1410 5g 25g T2951 1g 5g M1186 5g 25g T1562 5g N N N

SO2 CH3 CH3 CH CH CH3 CH3 Sulfur-Transfer

CH3 CH CH3 Reagents 1-(2,4,6-Triisopropyl- 1-(2,4,6-Triisopropyl- 2,4,5,6-Tetramethylbenzene- benzenesulfonyl)imidazole benzenesulfonyl)-1,2,4-triazole 2,4-Mesitylenedisulfonyl Dichloride disulfonyl Dichloride CAS RN: 50257-40-4 CAS RN: 54230-60-3 CAS RN: 68985-08-0 CAS RN: 97997-76-7 B3125 1g 5g B3623 5g 25g X0001 25g 100g 500g D0059 5g 25g

O S N S Riboses and S S H N S O 2 2'-Deoxyriboses 3H-1,2-Benzodithiol-3-one 1,1-Dioxide Bis(phenylacetyl) Disulfide Xanthane Hydride 2-Deoxy-D-ribose CAS RN: 66304-01-6 CAS RN: 15088-78-5 CAS RN: 6846-35-1 CAS RN: 533-67-5

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T2607 5g 25g M1965 1g 5g R0066 5g 25g R0067 5g 25g T2641 5g 25g

1,2,3-Tri-O-acetyl-5-deoxy- β-D-Ribofuranose 1,3,5-Tri-O-benzoyl- β-D-ribofuranose Methyl β-D-Ribofuranoside Tetra-O-acetyl-β-D-ribofuranose 1-Acetate 2,3,5-Tribenzoate α-D-ribofuranose CAS RN: 62211-93-2 CAS RN: 7473-45-2 CAS RN: 13035-61-5 CAS RN: 6974-32-9 CAS RN: 22224-41-5 D4207 1g 5g D4594 1g 5g R0025 25g 250g R0068 1g 5g 25g R0080 1g BzO F BzO O O F O OBz F OBz 2-Deoxy-2,2-difluoro-D- OBz erythro-pentonic Acid 2-Deoxy-2-fluoro-1,3,5-tri-O- β-L-Ribofuranose 1-Acetate γ-Lactone 3,5-Dibenzoate benzoyl-α-D-arabinofuranose D-(-)-Ribose L-Ribose 2,3,5-Tribenzoate CAS RN: 122111- 01-7 CAS RN: 97614-43-2 CAS RN: 50-69-1 CAS RN: 24259-59-4 CAS RN: 3080-30-6

R0082 5mg R0026 100mg 1g R0083 Please contact us. C3326 200mg 1g

Cl 5'-O- O CH3 P Triphosphorylation O N CH3 CH3 CH3 α-D-Ribose 1,5-Bis(phosphate) Ribose-5-phosphate Reagents 5-Chlorosaligenyl-N,N- Tetrasodium Salt Barium Salt Hydrate β-D-Ribose 1,5-Bis(phosphate) diisopropylphosphoramidite CAS RN: 113599-17-0 CAS RN: 15673-79-7 Tetrasodium Salt CAS RN: 1620086-77-2 B5440 200mg 1g T0431 25g 100g 500g H0424 25g 100g 500g O O O P O P O O OH OH OH Deprotection

CF3 OH CF3 CF3 2 (C4H9)4N Reagents Bis(tetrabutylammonium) Dihydrogen Pyrophosphate Trifluoroacetic Acid HFIP CAS RN: 857447-79-1 CAS RN: 76-05-1 CAS RN: 920-66-1

Magaña, K. Wrobel, Y. Alvarado Caudillo, S. Zaina, G. Lund, K. Wrobel, References Anal. Biochem. 2008, 374, 378; M. Münzel, D. Globisch, T. Brückl, M. 1) H. Vorbrüggen, C. Ruh-Pohlenz, in Handbook of Nucleoside Synthesis, Wagner, V. Welzmiller, S. Michalakis, M. Müller, M. Biel, T. Carell, Wiley-Interscience, New York, 2001; H. Vorbrüggen, C. Ruh-Pohlenz, Angew. Chem. Int. Ed. 2010, 49, 5375. in Organic Reactions, ed. by L. A. Paquette et al., John Wiley & Sons, 3) I. Okamoto, K. Shohda, K. Seio, M. Sekine, J. Org. Chem. 2003, 68, 2000, Vol. 55; D. M. Huryn, M. Okabe, Chem. Rev. 1992, 92 , 1745; E. 9971; A. Misra, S. Mishra, K. Misra, Bioconjugate Chem. 2004, 15, 638.; Ichikawa, K. Kato, Curr. Med. Chem. 2001, 8, 385. R. Gukathasan, M. Massoudipour, I. Gupta, A. Chowdhury, S. Pulst, S. 2) Z. Liu, S. Liu, Z. Xie, W. Blum, D. Perrotti, P. Paschka, R. Klisovic, J. Byrd, Ratnam, Y. S. Sanghvi, S. A. Laneman, J. Organomet. Chem. 2005, 690, K. K. Chan, G. Marcucci, Nucleic Acids Res. 2007, 35, e31; A. Alcázar 2603.

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