1. chem960
  2. 961-07-9
2'-Deoxyguanosine | 961-07-9

Product name:2'-Deoxyguanosine

CAS No:961-07-9
MF:C10H13N5O4
MW:267.241321325302
MDL:MFCD00080300
CID:40416
PubChem ID:135398592
Names and Identifiers
  • 2'-Deoxyguanosine
  • 2'-DEOXY-D-GUANOSINE
  • 9-(2'-DEOXY-BETA-D-RIBOFURANOSYL)GUANINE
  • A-2'-DEOXYGUANOSINE
  • DEOXYGUANOSINE-2'
  • GUANINE DESOXYRIBOSIDE
  • 2’-deoxy-guanosin
  • 9H-Purin-6-ol, 2-amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-deoxyephedrinearenol2’-deoxyguanosine
  • deoxyguanosine
  • Desoxyguanosine
  • Guanine deoxy nucleoside
  • Guanine deoxyriboside
  • Guanine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-guaninedeoxyriboside
  • Guanosine, 2'-deoxy-NSC 22837
  • 9-(2-Deoxy-β-D-ribofuranosyl)guanine
  • Guanine-2'-deoxyriboside
  • 2`-Deoxyguanosine
  • 2-Amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one hydrate
  • 2'-Deoxyguanosine hydrate
  • 2'-Deoxyguanosine Monohydrate
  • 2-Deoxyguanosine Hydrate
  • AMMoniuM nitrate -15N2
  • 9-(2-Deoxy-beta-D-ribofuranosyl)guanine hydrate
  • Guanine-2'-deoxyriboside monohydrate
  • 9-(2-Deoxy-beta-D-ribofuranosyl)guanine
  • 2-dG
  • Guanosine, 2'-deoxy-
  • 2'-DEOXY-GUANOSINE
  • 2
  • -Deoxyguanosine
  • 2-Amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
  • Guanine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-
  • 9H-Purin-6-ol, 2-amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-
  • G9481N71RO
  • C00330
  • 9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine
  • 2'-Deoxyguanosine hyd
  • 2′-Deoxyguanosine hydrate
  • 2′-Deoxyguanosine (ACI)
  • 11: PN: EP4155418 SEQID: 65 claimed sequence
  • 13: PN: CN104513856 PAGE: 2 claimed sequence
  • 212: PN: WO2012148497 TABLE: 6 claimed sequence
  • 2′-Deoxyguanine
  • 4: PN: WO2022090733 SEQID: 576 claimed sequence
  • 59: PN: WO2022263569 PAGE: 208 claimed sequence
  • 6: PN: US20230098408 SEQID: 65 claimed sequence
  • 9-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine
  • D
  • Deoxyguanosine
  • Guanine, 9-(2-deoxy-β-D-erythro-pentofuranosyl)-
  • MeSH ID: D003849
  • NSC 22837
  • AB00682067-01
  • YKBGVTZYEHREMT-UHFFFAOYSA-N
  • SY019850
  • Guanine, 9-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-
  • 9H-Purin-6-ol, 2-amino-9-(2-deoxy-9-.beta.-D-ribofuranosyl)-
  • Oprea1_013861
  • YKBGVTZYEHREMT-UHFFFAOYSA-
  • NCGC00096112-01
  • DTXSID00862488
  • 2-amino-9-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one
  • MFCD00080300
  • 686353-29-7
  • AKOS016368229
  • Oprea1_263480
  • NSC-22837
  • InChI=1/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)
  • Oprea1_301732
  • SCHEMBL10068103
  • 2-amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
  • 2-Amino-9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
  • AKOS015997869
  • 2 inverted exclamation mark -Deoxyguanosine(contains <7%H2O)
  • 2'-Deoxyguanosine-15N5
  • 2-Amino-9-(2-deoxypentofuranosyl)-9H-purin-6-ol
  • NSC22837
  • NS00008000
  • HMS3369B16
  • MDL:MFCD00080300
  • InChIKey:YKBGVTZYEHREMT-KVQBGUIXSA-N
  • Inchi:1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1
  • SMILES:O=C1N=C(N)NC2N([C@H]3C[C@H](O)[C@@H](CO)O3)C=NC1=2
  • BRN:39814
Chemical and Physical Properties

Computed Properties

  • Exact Mass: 285.10700
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 6
  • Rotatable Bond Count: 2
  • Monoisotopic Mass: 267.097
  • Heavy Atom Count: 19
  • Complexity: 417
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1
  • XLogP3: -0.9
  • Tautomer Count: 6
  • Surface Charge: 0
  • Topological Polar Surface Area: 135
  • Molecular Weight: 267.24

Experimental Properties

  • LogP: -1.14060
  • PSA: 148.51000
  • Refractive Index: -42 ° (C=0.2, 1mol/L NaOH)
  • Water Partition Coefficient: Slightly soluble in water.
  • Boiling Point: 725.5°C at 760 mmHg
  • Melting Point: 300 ºC
  • Flash Point: 725.5°Cat760mmHg
  • Solubility: NH4OH 1 M: 50 mg/mL, clear to very faintly turbid, yellow to brown
  • Color/Form: 300°C
  • Solubility: Soluble in water. It is easily hydrolyzed by dilute inorganic acids.
  • Density: 1.3382 (rough estimate)
Security Information
  • Symbol: GHS07
  • RTECS:MF8760000
  • WGK Germany:3
  • Safety Instruction:S24/25
  • Hazard Statement:H302+H312+H332
  • Warning Statement:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501
  • Prompt:warning
  • Storage Condition:Powder -20°C 3 years   4°C 2 years In solvent -80°C 6 months   -20°C 1 month
  • Hazard Category Code:20/21/22
  • TSCA:Yes
  • FLUKA BRAND F CODES:10-23
Customs Data
  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synthetic Circuit

Synthetic Circuit 1

Reaction Conditions
1.1 Reagents: tert-Butanol ,  Nitrous oxide Solvents: Water ;  pH 7
Reference
Radical-based alkylation of guanine derivatives in aqueous medium
Chatgilialoglu, Chryssostomos; Caminal, Clara; Mulazzani, Quinto G., Organic & Biomolecular Chemistry, 2011, 9(9), 3494-3498

Synthetic Circuit 2

Reaction Conditions
1.1 Reagents: Azobisisobutyronitrile ,  Tributylstannane Solvents: Toluene
1.2 Solvents: Dichloromethane ,  Water
1.3 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
Reference
Preparation of deoxynucleosides via homolytic deoxygenation reactions
, World Intellectual Property Organization, , ,

Synthetic Circuit 3

Reaction Conditions
1.1 Catalysts: Purine nucleoside phosphorylase ,  Calcium chloride Solvents: Water
Reference
Process for selectively producing 1-phosphorylated sugar derivative anomer and process for producing nucleoside
, World Intellectual Property Organization, , ,

Synthetic Circuit 4

Reaction Conditions
1.1 Catalysts: Nucleoside deoxyribosyltransferase Solvents: Diethylene glycol ,  Water ;  4 h, pH 6.5, 40 °C
Reference
One-step enzymatic synthesis of nucleosides from low water-soluble purine bases in non-conventional media
Fernandez-Lucas, Jesus; Fresco-Taboada, Alba; de la Mata, Isabel; Arroyo, Miguel, Bioresource Technology, 2012, 115, 63-69

Synthetic Circuit 5

Reaction Conditions
1.1 Reagents: Monopotassium phosphate Solvents: Water ;  1 d, pH 7.1, 60 °C
Reference
Production of nucleosides by immobilized Escherichia coli cells expressing uridine phosphorylase and purine nucleoside phosphorylase
, European Patent Organization, , ,

Synthetic Circuit 6

Reaction Conditions
1.1 Reagents: Methylamine Solvents: Water
Reference
The thermal N9/N7 isomerization of N2-acylated 2'-deoxyguanosine derivatives in the melt and in solution
Golankiewicz, Bozenna; Ostrowski, Tomasz; Leonard, Peter; Seela, Frank, Helvetica Chimica Acta, 2002, 85(1), 388-398

Synthetic Circuit 7

Reaction Conditions
1.1 Reagents: Sodium hydroxide ,  Hydrochloric acid Catalysts: Nucleoside deoxyribosyltransferase Solvents: Water ;  16 h, pH 6 - 6.3, 40 °C
1.2 Reagents: Sodium hydroxide Solvents: Water
1.3 Reagents: Sodium hydroxide ,  Hydrochloric acid Catalysts: Adenosine deaminase Solvents: Water ;  13 h, 7.8 atm, 40 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  2 min, reflux
Reference
Enzymatic synthesis of 2'-deoxyguanosine with nucleoside deoxyribosyltransferase-II
Okuyama, Kiyoshi; Shibuya, Susumu; Hamamoto, Tomoki; Noguchi, Toshitada, Bioscience, 2003, 67(5), 989-995

Synthetic Circuit 8

Reaction Conditions
1.1 3.5 h
Reference
Synthesis of 9-β-D-arabinofuranosylguanine by combined use of two whole cell biocatalysts
Medici, Rosario; Iribarren, Adolfo M.; Lewkowicz, Elizabeth S., Bioorganic & Medicinal Chemistry Letters, 2009, 19(15), 4210-4212

Synthetic Circuit 9

Reaction Conditions
1.1 Catalysts: Adenosine deaminase Solvents: Dimethyl sulfoxide ,  Water ;  24 h, pH 7.4, rt
Reference
Synthesis of 2'-deoxyguanosine from 2'-deoxyadenosine via C2 nitration
Xia, Ran; Chen, Lei-Shan; Xu, Shao-Hong; Xia, Chao; Sun, Li-Ping, Nucleosides, 2022, 41(7), 593-604

Synthetic Circuit 10

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water
Reference
Enzymic manufacture of glyoxal-guanosines and preparation of guanosines from them
, Japan, , ,

Synthetic Circuit 11

Reaction Conditions
1.1 Reagents: Sodium hydroxide
Reference
Modification of guanine bases: reaction of guanine nucleosides with aryl and chlorosulfonyl isocyanates
Camus, Philippe; Lhomme, M. France; Lhomme, Jean, Tetrahedron Letters, 1989, 30(4), 467-70

Synthetic Circuit 12

Reaction Conditions
1.1 Reagents: Potassium carbonate ,  Monopotassium phosphate Solvents: Water ;  pH 10, 45 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 10, 45 °C
1.3 Catalysts: Purine nucleoside phosphorylase (immobilized onto glyoxal agarose gel) ,  Uridine phosphorylase (immobilized onto Sepabeads coated with polyethyleneamine followed by crosslinking with aldehyde-dextran) ;  45 °C
1.4 Reagents: Hydrochloric acid Solvents: Water ;  24 h, pH 10, 45 °C
1.5 Reagents: Potassium carbonate Solvents: Water ;  pH 10, rt → 4 °C
1.6 Reagents: Hydrochloric acid Solvents: Water
Reference
Synthesis of 2'-deoxynucleosides by transglycosylation with new immobilized and stabilized uridine phosphorylase and purine nucleoside phosphorylase
Ubiali, Daniela; Rocchietti, Silvia; Scaramozzino, Francesca; Terreni, Marco; Albertini, Alessandra M.; et al, Advanced Synthesis & Catalysis, 2004, 346(11), 1361-1366

Synthetic Circuit 13

Reaction Conditions
1.1 Catalysts: Purine nucleoside phosphorylase (immobilized) Solvents: Water ;  8 h, pH 10, 45 °C
Reference
Immobilization and Stabilization of Recombinant Multimeric Uridine and Purine Nucleoside Phosphorylases from Bacillus subtilis
Rocchietti, Silvia; Ubiali, Daniela; Terreni, Marco; Albertini, Alessandra M.; Fernandez-Lafuente, Roberto; et al, Biomacromolecules, 2004, 5(6), 2195-2200

Synthetic Circuit 14

Reaction Conditions
1.1 Catalysts: Adenosine deaminase
Reference
Nucleic acid related compounds. 96. Synthesis of sugar-modified 2,6-diaminopurine and guanine nucleosides from guanosine via transformations of 2-aminoadenosine and enzymic deamination with adenosine deaminase
Robins, Morris J.; Zou, Ruiming; Hansske, Fritz; Wnuk, Stanislaw F., Canadian Journal of Chemistry, 1997, 75(6), 762-767

Synthetic Circuit 15

Reaction Conditions
1.1 Reagents: Sodium hydroxide Catalysts: Purine nucleoside phosphorylase Solvents: Water
Reference
Process for producing nucleoside compound
, World Intellectual Property Organization, , ,
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1P003A2A-100g 95% In Stock USA 100g $236.00/ ¥1,714.12 15 Dec. 2023
1P003A2A-25g 95% In Stock USA 25g $60.00/ ¥435.79 15 Dec. 2023
1P003A2A-5g 95% In Stock USA 5g $16.00/ ¥116.21 15 Dec. 2023
1P003A2A-1g 95% In Stock USA 1g $7.00/ ¥50.84 15 Dec. 2023
1P003A2A-1mg 95% In Stock USA 1mg $4.00/ ¥29.05 15 Dec. 2023
Brand:aaron Supplier:Aaron
No. Purity Stock Specification Price update time operate
AR003AAM-10g 98% In China Stock 10g $25.00/ ¥181.58 13 Dec. 2023
AR003AAM-5g 98% In China Stock 5g $13.00/ ¥94.42 13 Dec. 2023
AR003AAM-1g 98% In China Stock 1g $5.00/ ¥36.32 13 Dec. 2023
AR003AAM-100g 98% In China Stock 100g $214.00/ ¥1,554.32 13 Dec. 2023
AR003AAM-25g 98% In China Stock 25g $59.00/ ¥428.53 13 Dec. 2023
Brand:targetmol Supplier:TargetMol Chemicals
No. Purity Stock Specification Price update time operate
T22218-20mg 98% 现货(一周内发货) 20mg ¥ 170 15 Sep. 2023
T22218-1 mL * 10 mM (in DMSO) 98% 现货(一周内发货) 1 mL * 10 mM (in DMSO) ¥ 180 15 Sep. 2023
T22218-20 mg 98% 现货(一周内发货) 20mg ¥ 170 11 Jul. 2023
Brand:scbt Supplier:圣克鲁斯生物技术
No. Purity Stock Specification Price update time operate
sc-500624-1mg 1mg ¥4813.00 05 Sep. 2023
sc-500624-1 mg 1mg ¥4,813.00 11 Jul. 2023
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