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Genetic information is stored in DNA as combinatorial 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 to a or 2’-, which can be nucleotides are used clinically as medicinal agents such as phosphorylated producing nucleotides. 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 moiety. Some In addition to this, the development of Chain representative examples of these are 9-[(2-hydroxyethoxy) Reaction (PCR) methodology has brought a dramatic change methyl] (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 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 β-D-arabinofuranoside genome and analyses of “Single 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 , due attention from the scientific .2) siRNAs and DNA , as 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'- (Bz-DMT-dA), have been used for chemical synthesis of DNA and RNA.

A0559 10mg A2033 100mg 1g

Pyrimidine Nucleosides and Their Analogs Nucleosides

6-Azauridine [54-25-1] 5-Azacytidine [320-67-2] A2052 1g 5g A2073 5g 25g A2232 20mg 100mg A2356 1g 5g A2431 1g

NH2

N N

HO O N O

1-(3,5-Anhydro-2-deoxy- OH 2,2'-O-Anhydro- Azidothymidine β-D-threo-pentofuranosyl)- 5-Aza-2'- 1-β-D-Arabinofuranosyl- 5-methyluridine [30516-87-1] [7481-90-5] [2353-33-5] [3083-77-0] [22423-26-3] A2528 50mg A2942 25mg 100mg B0666 100mg 1g B1575 1g 5g B3087 1g 5g

O O

C NH2 N HN

HO N NH2 HO O N O O

4 OH OH OH N3 N -Benzoyl-5'-O- 2'-Azido-2'- 5-Bromo-2'-deoxyuridine (4,4'-dimethoxytrityl)-2'- Acadesine [2627-69-2] [26929-65-7] 5-Bromouridine [957-75-5] [59-14-3] deoxycytidine [67219-55-0]

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B3094 1g 5g B3102 100mg 1g B3404 100mg B3631 1g 5g C0522 1g 5g 25g

N4-Benzoyl-3',5'-O-(1,1,3,3- N4-Benzoylcytidine N4-Benzoyl-2'-deoxycytidine tetraisopropyl-1,3-disiloxanediyl)- [13089-48-0] [4836-13-9] Brivudine [69304-47-8] [69304-43-4] Cytidine [65-46-3] C0525 100mg 1g C2035 1g 5g C2207 1g 5g C2208 5g 25g C2878 1g 5g O NH C O(CH2)4CH3 F N

H3C O N O

OH OH Cytidine Sulfate 2,2'-O-Cyclocytidine 2,2'-O-Cyclouridine [32747-18-5] Cytarabine [147-94-4] Hydrochloride [10212-25-6] [3736-77-4] Capecitabine [154361-50-9] D0048 5g 25g D0060 1g 5g 25g D2235 100mg 500mg 1g D3566 5g 25g D3579 1g 5g

2'-Deoxycytidine 2'-Deoxy-5-fluorouridine 5'-O-(4,4'-Dimethoxytrityl)- 5'-Deoxy-5-fluorouridine Hydrochloride [3992-42-5] 2'-Deoxyuridine [951-78-0] [50-91-9] [40615-39-2] [3094-09-5] D3580 1g 5g D3583 1g 5g D3610 100mg 500mg 5g D3614 1g D3615 1g 5g

2'-Deoxycytidine 2'-Deoxy-5-methylcytidine 2'-Deoxy-2'-fluorocytidine 2'-Deoxy-2'-fluorouridine Stavudine [3056-17-5] [951-77-9] [838-07-3] Hydrate [10212-20-1] [784-71-4] D3642 1g D4200 10mg D4220 50mg 200mg D4342 1g 5g D4823 200mg 1g

O NH2 NH2 O

I CH2OH F HN N N HN

HO O N HO O N H3C O N HO O N F H3C O O O O

OH OH OH OH OH F 2'-Deoxy-5-fluorocytidine 2'-Deoxy-5-(hydroxymethyl)- 5'-Deoxy-5-fluorocytidine (2'R)-2'-Deoxy-2'-fluoro-2'- [10356-76-0] Fialuridine [69123-98-4] cytidine [7226-77-9] [66335-38-4] methyluridine [863329-66-2] E1057 50mg 200mg E1093 50mg 200mg F0534 1g F0635 5g 25g F0636 1g 5g

O NH2 C CH C CH HN N

HO O N HO O N O O

OH OH 5-Ethynyl-2'-deoxyuridine 5-Ethynyl-2'-deoxycytidine 5-Fluorocytidine [61135-33-9] [69075-47-4] [2341-22-2] Tegafur [17902-23-7] 5-Fluorouridine [316-46-1] G0367 100mg 1g I0258 1g 5g 25g I0882 1g L0217 100mg 1g M1405 1g 5g 25g

NH2 I N

HO O N O

OH Gemcitabine Hydrochloride 5-Iodo-2'-deoxycytidine 5-Methyluridine [122111- 03-9] Idoxuridine [54-42-2] [611-53- 0] Lamivudine [134678-17-4] [1463-10-1] M1931 1g M2290 1g 5g M2317 200mg 1g M2399 50mg 250mg R0077 100mg 500mg

O NH2 O

C NH2 HN N N

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

OH OCH3 OH OCH3 OH OH 5-Methylcytidine 2'-O-Methyluridine 2'-O-Methylcytidine [2140-61-6] [2140-76-3] [2140-72-9] Mizoribine [50924-49-7] Ribavirin [36791-04-5]

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T0233 1g 5g 25g T2511 100mg 1g T2549 5g 25g U0020 5g 25g Z0022 200mg 1g

N

HO O N O

OH OH Trifluorothymidine 2',3',5'-Tri-O-acetyluridine Thymidine [50-89-5] [70-00-8] [4105-38-8] [58-96-8] Zebularine [3690-10-6] A0152 5g 25g 100g A1915 1g 5g 25g A2054 1g 5g A2135 5g 25g

Purine Nucleosides 2-Amino-6-chloropurine 2-Aminoadenosine [58-61-7] Acyclovir [59277-89-3] Riboside [2004-07-1] [2096-10-8] A2414 100mg 1g A2739 10mg 50mg B3093 1g 5g B3101 100mg 1g B3103 100mg 1g O

N NH

HO N N NH HO 2 O 6 . xH O OH 2 N -Benzoyl-5'-O- 9-β-D- N6-Benzoyl- (4,4'-dimethoxytrityl)- Adefovir Dipivoxil Arabinofuranosylguanine N6-Benzoyladenosine 2'-deoxyadenosine 2'-deoxyadenosine [142340-99-6] Hydrate [38819-10-2] Hydrate [4546-55-8] Hydrate [206752-42-3] [64325-78-6] B3460 100mg 1g B4001 200mg 1g B4002 1g 5g C2192 100mg 1g C2206 1g 5g O O

N NH N NH

HO Br N N NH2 HO Br N N NH2 O O . 6 xH2O N -Dibenzoyladenosine OH OH OH 2',3'-Dibenzoate 8-Bromo-2'- 8-Bromoguanosine 2-Chloroadenosine Hydrate 6-Chloropurine Riboside [58463-04-0] [13389-03-2] Hydrate [4016-63-1] [146-77-0] [5399-87-1] C2499 50mg C2500 20mg 100mg C2689 25mg C2815 25mg D0046 5g 25g

NH2 NH2 NH2

N N N N N N

HO N N Cl HO N N HO N N O O O . xH2O OH OH OH Cordycepin from Cordyceps 2'-Deoxyadenosine Cladribine [4291-63-8] Clofarabine [123318-82-1] militaris [73-03-0] Cordycepin Hydrate [73-03-0] Monohydrate [16373-93-6] D0052 1g 5g 25g D3065 100mg D3066 100mg 500mg D3584 1g 5g D4137 5g

2'-Deoxyguanosine Hydrate 2',3'-Dideoxyadenosine 2'-Deoxyadenosine [961-07-9] [4097-22-7] Didanosine [69655-05-6] 2'-Deoxyinosine [890-38-0] Anhydrous [958-09-8] D4228 25mg D4256 1g 5g D4292 100mg 1g E0899 50mg 200mg F0656 200mg 1g O NH2 O

HN CH3 Cl N N N HN N N N . H2O O N N N N O HO N Cl H2N N N O OCH2CH3 O CH2CH2OCH2 P CH2 OCH2CH3 O P O O CH3 ONa OH OH O Diethyl [[2-(6-Amino-9H- HO CH2OH Dibutyryl cAMP Sodium purin-9-yl)ethoxy]methyl]- 5,6-Dichlorobenzimidazole Entecavir Monohydrate 2-Fluoroadenosine Salt [16980-89-5] phosphonate [116384-53-3] 1-β-D-Ribofuranoside [53-85-0] [209216-23-9] [146-78-1] F0842 500mg 5g G0171 5g 25g 100g G0315 5g 25g H1290 5g 25g H1291 1g 5g

O NH2

N N HN N . xH2O N N O H2N N N H2N N N N N CH2O C CH3 CH OH CH CH CH 2 2 2 CH2OCH CH CH2O C CH3 CH2OH 3 O OH Ganciclovir Hydrate 9-(2-Hydroxyethyl)- (R)-9-(2-Hydroxypropyl)- Famciclovir [104227-87-4] [118-00-3] [82410-32-0] [707-99-3] adenine [14047-28-0]

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I0037 25g 500g I0697 1g 5g I0699 100mg 1g I0700 100mg 1g I0702 5g 25g

N2-Isobutyryl-5'-O- (4,4'-dimethoxytrityl)-2'- N2-Isobutyrylguanosine N2-Isobutyryl-2'-deoxy- 2',3'-O-Isopropylidene- [58-63-9] deoxyguanosine [68892-41-1] Monohydrate [64350-24-9] guanosine [68892-42-2] adenosine [362-75-4] I0703 5g I0704 5g I0759 200mg 1g 5g M2291 1g M2318 200mg 1g

NH2 O

N N N NH

HO N N HO N N NH2 O O

. xH2O OH OCH3 OH OCH3 2',3'-O-Isopropylidene- 2',3'-O-Isopropylidene- 2-Iodoadenosine 2'-O-Methyladenosine 2'-O-Methylguanosine guanosine [362-76-5] inosine [2140 -11- 6] [35109-88-7] [2140-79-6] Hydrate [2140-71-8] O0401 200mg 1g P2164 200mg 1g P2311 25mg 100mg T2690 1g T2691 1g 5g

O CH3 CH3 NH2 N

HN N HN N N N

HO N N HO O N N H N N N 2 O CH2OH CH3O O CH2CH2CH NH2 CH2OH NH OH . 2HCl OH OH O 2',3',5'-Tri-O-acetyl-2-amino- 2',3',5'-Tri-O-acetyl- 8-Oxoadenosine Puromycin 6-chloropurine Riboside 6-chloro-2-iodopurine [29851-57-8] Penciclovir [39809-25-1] Dihydrochloride [58-58-2] [16321-99-6] Riboside [5987-76-8] T2692 1g 5g V0098 1g 5g V0111 100mg 1g X0008 100mg

2',3',5'-Tri-O-acetylguanosine Vidarabine Monohydrate Valacyclovir Hydrochloride Dihydrate [6979-94-8] [24356-66-9] Hydrate [124832-27-5] [146-80-5]

Nucleotides and Their Analogs Nucleotides are formed from the condensation of nucleoside which is either ribose (RNA) or 2’-deoxyribose (DNA). and a 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 .

C0523 10mg 100mg 1g C0524 1g 5g

Pyrimidine Nucleotides and Their Analogs Nucleotides Cytidine 5'-Diphosphate Cytidine 5'-Monophosphate Trisodium Salt Hydrate Disodium Salt Hydrate [34393-59-4] [6757-06-8] C1675 1g 5g D3673 100mg 1g T0845 100mg U0021 5g 25g U0022 100mg

Cytidine 2'-Deoxycytidine Thymidine 5'-Monophosphate Uridine 5'-Monophosphate Uridine 5'-Triphosphate 5'-Monophosphate 5'-Monophosphate Hydrate Disodium Salt Hydrate Disodium Salt Hydrate Trisodium Salt Hydrate [63-37-6] [1032-65-1] [33430-62-5] [3387-36-8] [19817-92-6]

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A0157 1g 5g 25g A0158 1g 5g 25g A0626 100mg 1g A2112 100mg 1g

Purine Nucleotides Adenosine 5'-Triphosphate Adenosine 5'-Diphosphate Adenosine 3',5'-Cyclic Disodium Salt Hydrate Disodium Salt Hydrate Monophosphate Sodium [34369-07-8] 5'-Adenylic [61-19-8] [16178-48-6] Salt Hydrate [37839-81-9] A2381 1g 5g F0913 25mg 100mg G0172 25g 100g I0036 1g 5g 25g I0038 100mg

NH2

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

Adenosine 3',5'-Cyclic OH Guanosine 5'-Monophosphate Inosine 5'-Monophosphate Inosine 5'-Triphosphate Monophosphate Hydrate Fludarabine Monophosphate Disodium Salt Hydrate Disodium Salt Hydrate Trisodium Salt Hydrate [60-92-4] [75607-67-9] [5550-12-9] [4691-65-0] [35908-31-7] I0039 100mg

Inosine 5'-Monophosphate Barium Salt Hydrate [3249-92-1] D3545 5g 25g R0022 25g R0024 25g Deoxyribonucleic Acid Ribonucleic Acid Ribonucleic Acid Sodium Sodium Salt from from Yeast Salt from Yeast Salmon Milt [9007-49-2] Nucleic Acids

D1140 100mg P0251 100mg D0919 1g 5g Deoxyribonuclease from Phosphatase, Acid from β-NAD Hydrate, oxidized Bovine Spleen Wheat Germ form and Coenzymes [9003-98-9] [9001-77-8] [53-84-9] related to 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 [606-68-8] [53-59-8] [1184-16 -3] T0521 100mg T2980 100mg T2979 100mg β-NADPH Tetrasodium Thionicotinamide Adenine Thionicotinamide Adenine Salt reduced form Dinucleotide Disodium Dinucleotide oxidized form [2646-71-1] Salt reduced form [4090-29-3]

Nucleobases and Their Analogs of these basic structures. For example, and , usually simply called “bases”, are a vital sense 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: such as adenine analogue 5-fluorouracil (5-FU) is used as an anticancer agent. and guanine; and 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.

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A2089 5g 25g A2670 1g 5g

O O

CH3 C Pyrimidine NH Nucleobases and Their Analogs N O Nucleobases H N4-Acetylcytosine [14631-20-0] 5-Acetyluracil [6214-65-9] A2136 1g 5g A2125 5g A2449 5g 25g A0947 25g A0898 5g 25g

O O

H2N NH NH

H2N N O N O H CH 4-Amino-5-fluoro- 3 4-Amino-6-chloropyrimidine 2-methoxypyrimidine 6-Amino-1-methyluracil 5-Aminoorotic Acid [5305-59-9] [1993-63-1] [2434-53-9] [7164-43-4] 5-Aminouracil [932-52-5] A0658 25g 250g A0558 1g 5g B3169 5g B0665 25g C1057 5g 25g

O O

NH NH

H2N N O ClCH2 N O H H

N4-Benzoylcytosine 6-Chloromethyluracil 6-Aminouracil [873-83-6] 6-Azauracil [461-89-2] [26661-13-2] 5-Bromouracil [51-20-7] [18592-13-7] C2300 5g 25g C0969 5g 25g C2093 5g 25g C0528 5g 25g 100g D1136 1g 5g

O

CH3 NH

CH3 N O H

6-Chloro-3-methyluracil 5,6-Dimethyluracil [4318-56-3] 5-Chlorouracil [1820-81-1] 6-Chlorouracil [4270-27-3] Cytosine [71-30-7] [26305-13-5] E0807 1g 5g E1096 200mg 1g F0321 1g 5g 25g F0382 100mg 1g F0151 5g 25g

O HC C NH

N O H

5-Ethynyluracil 5-Fluorocytosine 5-Fluoroorotic Acid 5-Ethyluracil [4212-49-1] [59989-18-3] [2022-85-7] Monohydrate [703-95-7] 5-Fluorouracil [51-21-8] I0531 1g 5g I0219 5g 25g I0814 5g M0204 100mg 1g 5g M2506 1g 5g

O O

O2N N NH

N NH2 CH3 N O H H 5-Iodo- 2,4-dimethoxypyrimidine 5-Methylcytosine 6-Methyl-5-nitrouracil [52522-99-3] 5-Iodouracil [696-07-1] Isocytosine [108-53-2] Hydrochloride [58366-64-6] [16632-21-6] M2355 1g 5g M0994 10g 25g M0443 25g 500g M0454 25g 500g N0281 5g 25g

OH O O O

O2N N NH NH NH

N SCH CH3 N S CH3 N O N O 3 H H H

2-Methylthio-4-pyrimidinol 5-Methyl-2-thiouracil 6-Methyl-2-thiouracil [5751-20-2] [636-26-0] [56-04-2] 6-Methyluracil [626-48-2] 5-Nitrouracil [611-08-5] O0065 25g 100g 500g P0236 1g 5g P0533 25g T0224 25g 250g T2757 1g

O O

NH NH

CH3CH2CH2 N S N S H H

Orotic Acid Monohydrate 6-Phenyl-2-thiouracil 6-Propyl-2-thiouracil [50887-69-9] [36822-11- 4] [51-52-5] 2-Thiouracil [141-90-2] 4-Thiouracil [591-28-6]

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T0234 5g 25g 100g T1622 1g 5g U0013 25g 100g 500g A0149 25g 250g

Purine Nucleobases 5-(Trifluoromethyl)uracil Thymine [65-71-4] [54-20-6] Uracil [66-22-8] Adenine [73-24-5] A0150 5g 25g A0151 25g 100g A0555 1g A0625 1g A0907 25g 250g

Adenine Hydrochloride Adenine Sulfate Dihydrate 8-Azahypoxanthine Hemihydrate [2922-28-3] [6509-19-9] [2683-90-1] 8-Azaguanine [134-58-7] [315-30-0] A1041 100mg 1g 5g A1111 200mg 1g A1248 1g 5g A1407 1g 5g A2068 5g 25g

NH2

N N N N H 4-Aminopyrazolo 2-Acetamido-6hydroxy- 2-Amino-6-chloropurine 2-Amino-6-iodopurine [3,4-d]pyrimidine [2380-63-4] 2-Aminopurine [452-06-2] purine [19962-37-9] [10310-21-1] [19690-23-4] A2069 5g 25g A2699 100mg A2805 25g 100g B1088 5g 25g B3344 5g 25g

NH2 O

CH3 N N N H2N NH2 N O N N O N N H CH H H 3 2 N6-Benzyladenine N6-Benzoyladenine [446-86-6] AHPP [5472-41-3] [317-34-0] [1214-39-7] [4005-49-6] B3355 5g 25g B3456 1g 5g B4134 1g B4454 200mg 1g C0278 5g 25g

O O

CH2 C C CH3 HN N HN N O N N Br O N N Br H CH3 CH3 8-Bromo-7-(2-butyn-1-yl)- 6-Benzyloxypurine 8-Bromotheophylline 8-Bromo-3-methyl- 3-methylxanthine [57500-07-9] [10381-75-6] xanthine [93703-24-3] [666816-98-4] 6-Chloropurine [87-42-3] C0293 25g 250g C2221 1g C2306 1g 5g C2575 1g 5g C2845 200mg 1g Cl

N N

N N

O

8-Chlorotheophylline 6-Chloro-2-fluoropurine 6-Chloro-7-deazapurine 2-Chloroadenine 6-Chloro-9-(tetrahydropyran- [85-18-7] [1651-29-2] [3680-69-1] [1839-18-5] 2-yl)purine [7306-68-5] C3130 1g 5g D1625 5g 25g D2470 1g 5g 25g D3604 25g D3894 1g 5g

Cl I N

N N H 6-Chloro-7-iodo-7- 2,6-Diaminopurine 2,6-Dichloropurine N2,9-Diacetylguanine 6-(Dimethylamino)purine deazapurine [123148-78-7] Monohydrate [1904-98-9] [5451-40-1] [3056-33-5] [938-55-6] D4284 1g 5g D4295 1g 5g D4324 1g F0647 200mg 1g G0168 1g 25g

Cl O Cl N N HN . HCl Cl N N Cl N N N H H H 2,6-Dichloro-7- 5,6-Dichlorobenzimidazole 7-Deazahypoxanthine 2-Fluoroadenine Guanine Sulfate Dihydrate deazapurine [90213-66-4] Hydrochloride [1087737-96-9] [3680-71-5] [700-49-2] [10333-92-3]

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G0169 1g 25g 250g G0170 25g H0311 5g 25g H1290 5g 25g I0370 100mg

Guanine Hydrochloride 9-(2-Hydroxyethyl)adenine Guanine [73-40-5] Hydrate [635-39-2] Hypoxanthine [68-94-0] [707-99-3] Isoguanine [3373-53-3] I0941 1g 5g K0009 1g 5g M0063 1g 5g M1925 1g 5g M2073 5g 25g

NH2 I N N N N H 3-Iodo-1H-pyrazolo- [3,4-d]pyrimidin-4-amine 6-Mercaptopurine 6-Methoxypurine 3-Methylxanthine [151266-23-8] Kinetin [525-79-1] Monohydrate [6112-76-1] [1074-89-1] [1076-22-8] M2432 50mg 200mg M2518 200mg 1g N0958 20mg 100mg T0212 1g 5g T0225 1g 5g

O NH2 OCH2

CH3 N N N N N N

O N N N N H2N NN H H H CH3 1-Methylxanthine 3-Methyladenine 2-Thioxanthine [6136-37-4] [5142-23-4] NU 2058 [161058-83-9] 6-Thioguanine [154-42-7] [2487-40-3] X0004 25g

Xanthine [69-89-6]

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

A0907 25g 250g A1915 1g 5g 25g A2033 100mg 1g Pharmacologically-Active Nucleosides and Nucleobases for Research and Experimental Use Allopurinol [315-30-0] Acyclovir [59277-89-3] 5-Azacytidine [320-67-2] A2052 1g 5g A2069 5g 25g A2232 20mg 100mg A2414 100mg 1g A2528 50mg

NH2 O

C NH2 N N N

HO O N HO N NH2 O O

OH Azidothymidine Adefovir Dipivoxil OH OH [30516-87-1] Azathioprine [446-86-6] Decitabine [2353-33-5] [142340-99-6] Acadesine [2627-69-2]

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A2694 1g 5g A2699 100mg A2737 200mg 1g A2739 10mg 50mg A2805 25g 100g

NH2 O NH NH2 N N NH O N N N CH3 N HO N N NH2 N N N N HO H2N O NH2 H2N N N N O N N O N N H . xH O CH3 H H OH 2 2 HO Abacavir [136470-78-5] AHPP [5472-41-3] PP 3 [5334-30-5] Ara-G Hydrate [38819-10-2] Aminophylline [317-34-0] B1575 1g 5g B3404 100mg C2035 1g 5g C2042 25g 500g C2499 50mg NH2 O N N CH3 CH3 N N HO N N Cl O NN O

CH3 5-Bromo-2'-deoxyuridine OH [59-14-3] Brivudine [69304-47-8] Cytarabine [147-94-4] [58-08-2] Cladribine [4291-63-8] C2500 20mg 100mg C2689 25mg C2815 25mg C2748 5g 25g C2878 1g 5g

NH2 NH2 O O NH C O(CH2)4CH3 N N N N F N CH3 CH2CH2Cl HO N N HO N N N N H C O N O O 3 . O N N O xH2O OH OH CH3 OH OH Cordycepin from Cordyceps 7-(2-Chloroethyl)- Clofarabine [123318-82-1] militaris [73-03-0] Cordycepin Hydrate [73-03-0] [5878-61-5] Capecitabine [154361-50-9] D2235 100mg 500mg 1g D3065 100mg D3066 100mg 500mg D3579 1g 5g D3580 1g 5g

2'-Deoxy-5-fluorouridine 2',3'-Dideoxyadenosine [50-91-9] [4097-22-7] Didanosine [69655-05-6] Doxifluridine [3094-09-5] Stavudine [3056-17-5] D3600 25g 500g D4228 25mg D4292 100mg 1g D4302 1g 25g D4342 1g 5g O NH2 HN CH3 Cl O F O OH N N N N CH3 CH3 CH2 CH CH2OH N N O N N O N N HO N Cl H3C O N O O O O O NN O N N O P O O CH3 CH3 ONa O OH OH CH3 OH OH Dibutyryl cAMP Sodium 5'-Deoxy-5-fluorocytidine [479-18-5] Salt [16980-89-5] DRB [53-85-0] [69975-86-6] [66335-38-4] D4823 200mg 1g E0899 50mg 200mg F0151 5g 25g F0321 1g 5g 25g F0635 5g 25g O O

HN HN N . H2O HO O N H2N N N H3C O CH2

OH F HO CH2OH Entecavir Monohydrate 5-Fluorocytosine PSI-6206 [863329-66-2] [209216-23-9] 5-Fluorouracil [51-21-8] [2022-85-7] Tegafur [17902-23-7] F0636 1g 5g F0842 500mg 5g F0913 25mg 100mg G0315 5g 25g G0367 100mg 1g NH 2 O N N N N O HN N . xH2O O HO P O N N F H2N N N HO H2N N N CH2O C CH3 CH OH CH CH CH OH O 2 2 2 CH2OCH CH2O C CH3 CH2OH O OH Fludarabine Monophosphate Ganciclovir Hydrate Gemcitabine Hydrochloride 5-Fluorouridine [316-46-1] Famciclovir [104227-87-4] [75607-67-9] [82410-32-0] [122111- 03-9] H0402 25g 500g H1430 5g 25g H1542 1g 5g I0258 1g 5g 25g K0009 1g 5g

O O H2N CH3CH3 O NH CH3 2 CH O 3 O OH H2N N N CH3 Co NH2 O H N N O CH3 O N CH3 CH2 CH CH3 CH3 N N N H2N CH3 O CH3 CH3 O NH2 O N NH CH3 O N N N CH N O 3 N CH3 CH3 O P O HO CH3 O O O CH2CH2OH HO Hydroxocobalamin Etofylline [519-37-9] Proxyphylline [603-00-9] Acetate [22465-48-1] Idoxuridine [54-42-2] Kinetin [525-79-1]

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L0217 100mg 1g M0063 1g 5g M2399 50mg 250mg M2742 1g N0958 20mg 100mg O H N O O 2 CH CH3 3 O CH NH2 3 O C NH2 H N OCH2 N 2 N CH3 N CH3 Co NH H 2 O N N CH3 H2N CH3 N N HO N OH CH CH3 O 3 NH2 O CH O NH N 3 O N CH3 H N NN CH3 O P O HO 2 O H . O xH2O OH OH HO 6-Mercaptopurine Methylcobalamin Hydrate Lamivudine [134678-17-4] Monohydrate [6112-76-1] Mizoribine [50924-49-7] [288315-09-3] NU 2058 [161058-83-9] P2164 200mg 1g P2311 25mg 100mg R0077 100mg 500mg T0179 25g 100g 500g T0212 1g 5g

O CH3 CH3 N

HN N N N

HO N N H N N N 2 O CH2OH CH3O CH2CH2CH NH2 CH2OH NH OH . 2HCl O Puromycin Penciclovir [39809-25-1] Dihydrochloride [58-58-2] Ribavirin [36791-04-5] Theophylline [58-55-9] 6-Thioguanine [154-42-7] T2511 100mg 1g T2744 500mg 5g T2941 25g V0098 1g 5g V0111 100mg 1g

O O

CH3 CH2 C OH N N

O N N

CH3 Trifluorothymidine Theophylline-7-acetic Vidarabine Monohydrate Valacyclovir Hydrochloride [70-00-8] Temozolomide [85622-93-1] Acid [652-37-9] [24356-66-9] Hydrate [124832-27-5]

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 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 into . 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.

A0082 100g 500g B0078 25g 100g 500g Protecting Agents for Nucleic Acid Synthesis Agents Hydroxy and Amino Groups Benzoic Anhydride Acetyl Chloride [75-36-5] [93-97-0] B0105 25mL 500mL B0511 10mL 100mL B0995 5g 25g 100g B1151 5g B1223 5mL 25mL 100mL

1,3-Benzodithiolylium Benzoyl Chloride Tetrafluoroborate tert-Butyldiphenyl- [98-88-4] BSA [10416-59-8] TBSCl [18162-48-6] [57842-27-0] chlorosilane [58479-61-1]

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C0306 25mL 100mL 500mL C0308 25g 100g 500g C0832 25g 100g 500g D1293 25mL 100mL 500mL D1608 5g 25g

1,3-Dichloro-1,1,3,3- Chlorotrimethylsilane 4-Chlorophenoxyacetyl N,N-Dimethylformamide tetraisopropyldisiloxane [75-77-4] Trityl Chloride [76-83-5] Chloride [4122-68-3] Dimethyl Acetal [4637-24-5] [69304-37-6] D1612 5g 25g D2334 5g 25g D2469 5g D2504 25g D3135 1g 5g

1,3-Dichloro-1,1,3,3- Di-tert-butylsilyl 4,4'-Dimethoxytrityl Chloride tetramethyldisiloxane Di-tert-butyldichlorosilane 2-Chlorotrityl Chloride Bis(trifluoromethanesulfonate) [40615-36-9] [2401-73-2] [18395-90-9] [42074-68-0] [85272-31-7] H0089 25mL 100mL 500mL I0115 25g 100g 500g M0721 25g 100g 500g M0790 25g 250g N0404 5g 25g

Isobutyryl Chloride 4-Methoxybenzoyl Chloride 4-Methoxytrityl Chloride 2-Nitrobenzyl Bromide HMDS [999-97-3] [79-30-1] [100-07-2] [14470-28-1] [3958-60-9] P0113 25g 500g P0677 25mL 500mL T0459 25g 500g T0512 25g 100g T0871 5g 25g 250g

Trimethylsilyl Phenoxyacetyl Chloride Pivaloyl Chloride 2,4,6-Triisopropylbenzene- Trifluoromethanesulfonate [701-99-5] [3282-30-2] sulfonyl Chloride [6553-96-4] Trityl Bromide [596-43-0] [27607-77-8] T1071 5g 25g T1526 1g B3125 1g 5g B3623 5g 25g Phosphorylating O and S S Phosphorothioating O 4,4',4''-Tris(4,5-dichloro- 4,4',4''-Tris(benzoyloxy)trityl phthalimido)trityl Bromide Agents 3H-1,2-Benzodithiol-3-one Bis(phenylacetyl) Disulfide Bromide [86610-66-4] [91898-93-0] 1,1-Dioxide [66304-01-6] [15088-78-5] C0976 5g 25g C0977 5g 25g C0978 5g 25g C1210 5g 25g C1215 5g 25g

2-Chlorophenyl 4-Chlorophenyl 2-Chloro-4H-1,3,2- Phosphorodichloridate Phosphorodichloridate Barium 2-Cyanoethylphosphate benzodioxaphosphorin- 2-Chloro-1,3,2-dioxa- [15074-54-1] [772-79-2] Hydrate [5015-38-3] 4-one [5381-99-7] phospholane [822-39-9] C1250 5g 25g C2228 1g 5g D0624 25g 500g D0764 25g D1059 25g 100g 500g

2-Chloro-2-oxo- 2-Cyanoethyl N,N,N',N'- Diethyl Dimethyl 1,3,2-dioxaphospholane Tetraisopropylphosphordiamidite Chlorothiophosphate Chlorothiophosphate Diphenyl Chlorophosphate [6609-64-9] [102691-36-1] [2524-04-1] [2524-03-0] [2524-64-3] D2624 5g D2883 25g D4211 1g 5g M0904 5g 25g 100g M0905 10g

CH3 CH3

CH3 N CH3 P (CH3)3CO OC(CH3)3 Dibenzyl N,N-Diisopropyl- Di-tert-butyl N,N- Methyl Methyl phosphoramidite Diphosphoryl Chloride Diisopropylphosphoramidite Phosphorodichloridate Dichlorophosphite [108549-23-1] [13498-14-1] [137348-86-8] [677-24-7] [3279-26-3]

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P0209 25g 500g P1223 1g B5440 200mg 1g C3326 200mg 1g P1744 500g

O O Cl O CH3 O P O P O P OH OH O N CH3 POCl3

2 (C4H9)4N CH3 CH3 Bis(tetrabutylammonium) 5-Chlorosaligenyl-N,N- Phenyl Dichlorophosphate Tetrabenzyl Dihydrogen Pyrophosphate diisopropylphosphoramidite (V) [770-12-7] Pyrophosphate [990-91-0] [857447-79-1] [1620086-77-2] Oxychloride [10025-87-3] T1895 25g B3020 25g C2325 5g 25g C2421 5g

S Cl P Cl Condensing Cl Agents 1-(Cyanomethyl)- Thiophosphoryl Chloride 5-(Benzylthio)-1H- 1,1'-Carbonyldi- piperidinium Tetrafluoroborate [3982-91-0] tetrazole [21871-47-6] (1,2,4-triazole) [41864-22-6] [434937-12-9] D0436 25g 400g D2026 25g 250g D3792 5g 25g E0670 1g 5g M0071 25g 500g

N,N'-Dicyclohexyl-4- N,N'-Dicyclohexylcarbodiimide 4,5-Dicyanoimidazole morpholinecarboxamidine 5-(Ethylthio)-1H-tetrazole 2-Mesitylenesulfonyl (= DCC) [538-75-0] [1122-28-7] [4975-73-9] [89797-68-2] Chloride [773-64-8] M0625 1g M1186 5g 25g N0477 1g 5g P0677 25mL 500mL T0340 25g 100g 500g

1-(2-Mesitylenesulfonyl)- 2,4-Mesitylenedisulfonyl 3-Nitro-1,2,4-triazole Pivaloyl Chloride imidazole [50257-39-1] Dichloride [68985-08-0] [24807-55-4] [3282-30-2] 1,2,4-Triazole [288-88-0] T0459 25g 500g T1017 5g 25g T1410 5g 25g T1562 5g T1985 5g 25g

1-(2,4,6-Triisopropyl- 2,4,5,6-Tetramethylbenzene- 2,4,6-Triisopropylbenzene- benzenesulfonyl)- disulfonyl Dichloride 1-(p-Toluenesulfonyl)- sulfonyl Chloride [6553-96-4] 1H-Tetrazole [288-94-8] imidazole [50257-40-4] [97997-76-7] imidazole [2232-08-8] T2951 1g 5g D0059 5g 25g D4207 1g 5g D4594 1g 5g N N N BzO F BzO SO2 F CH3 CH3 CH CH O O O CH3 CH3 and OBz CH3 CH OBz F OBz CH3 2'- 1-(2,4,6-Triisopropyl- 2-Deoxy-2,2-difluoro-D-erythro- 2-Deoxy-2-fluoro-1,3,5-tri-O- benzenesulfonyl)- 2-Deoxy-D-ribose pentonic Acid γ-Lactone benzoyl-α-D-arabinofuranose 1,2,4-triazole [54230-60-3] [533-67-5] 3,5-Dibenzoate [122111- 01-7] [97614-43-2] M1965 1g 5g R0025 25g 250g R0026 100mg 1g R0066 5g 25g R0067 5g 25g

Ribose-5-phosphate Tetra-O-acetyl- β-D-Ribofuranose Methyl β-D-Ribofuranoside Barium Salt Hydrate β-D-ribofuranose 1-Acetate 2,3,5-Tribenzoate [7473-45-2] D-(-)-Ribose [50-69-1] [15673-79-7] [13035-61-5] [6974-32-9] R0068 1g 5g 25g R0080 1g R0082 5mg R0083 Price on request T2607 5g 25g

β-L-Ribofuranose 1-Acetate α-D-Ribose 1,5-Bis(phosphate) 1,2,3-Tri-O-acetyl-5-deoxy- 2,3,5-Tribenzoate Tetrasodium Salt β-D-Ribose 1,5-Bis(phosphate) β-D-ribofuranose L-Ribose [24259-59-4] [3080-30-6] [113599-17- 0] Tetrasodium Salt [62211-93-2]

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T2641 5g 25g

1,3,5-Tri-O-benzoyl- α-D-ribofuranose [22224-41-5]

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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