118573-62-9

Basic information

• Product Name: 5-(3-aminopropyl)-2'-deoxyuridine
• Synonyms: 5-(3-aminopropyl)-2'-deoxyuridine
• CAS NO: 118573-62-9
• Molecular Formula: C₁₂H₁₉N₃O₅
• Molecular Weight: 0
• Mol File: 118573-62-9.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.394g/cm³
• CAS DataBase Reference: 5-(3-aminopropyl)-2'-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-aminopropyl)-2'-deoxyuridine(118573-62-9)
• EPA Substance Registry System: 5-(3-aminopropyl)-2'-deoxyuridine(118573-62-9)

Safety Data

• Hazardous Substances Data: 118573-62-9(Hazardous Substances Data)

Upstream product

• 250600-80-7 5-(3-N-(tert-Butoxycarbonyl)aminopropyl)-2'-deoxyuridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 114079-30-0 5-(3-N-(tert-Butoxycarbonyl)amino-1-propynyl)-2'-deoxyuridine 
• 115899-40-6 2,2,2-trifluoro-N-(3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-yn-1-yl)acetamide 

Downstream Products

• 250600-82-9 5-(3-N-(9-Fluorenylmethoxycarbonyl)aminopropyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine 
• 1236405-70-1 C₃₁H₃₂N₃O₆P 
• 1236405-71-2 C₃₁H₃₂N₃O₆P 
• 1236405-73-4 C₃₁H₃₂N₃O₆P 
• 1236405-59-6 C₄₄H₅₀N₄O₇P₂ 

Relevant articles and documents

Scope and Limitations of Typical Copper-Free Bioorthogonal Reactions with DNA: Reactive 2′-Deoxyuridine Triphosphates for Postsynthetic Labeling

Four triphosphates of 2′-deoxyuridine that carried the following bioorthogonally reactive groups were synthesized by organic-chemical methods. Two triphosphates with tetrazines and one with a cyclopropene moiety were designed for Diels-Alder reactions with inverse electron demand, and one triphosphate with a tetrazole core was designed for the photoclick cycloaddition. These triphosphates were not only successfully applied for oligonucleotide preparation by standard DNA polymerases, including Hemo KlenTaq, Vent, and Deep Vent, but also bypassed for full length primer extension products. Fluorescent labeling of the primer extension products was achieved by fluorophores with reactive counterparts and analyzed by polyacrylamide gel electrophoresis mobility shifts. The tetrazine-oligonucleotide conjugates were reacted with carboxymethylmonobenzocyclooctyne- and bicyclononyne-modified fluorophores. The yield of these postsynthetic reactions could significantly be improved by a more stable but still reactive nicotinic acid-derived tetrazine and by changing the key experimental conditions, mainly the pH of 7.2 and the temperature of 45-55 °C. The cyclopropene-oligonucleotide conjugate could be successfully labeled with a tetrazine-modified rhodamine in very good yields. The photoclick cycloaddition between tetrazole-oligonucleotide conjugates and a maleimide-modified dye worked quantitatively. The combination of primer extension, bypass, and bioorthogonal modification works also for double and triple labeling using the cyclopropene-modified 2′-deoxyuridine triphosphate.

Functionalization of mono- and oligonucleotides with phosphane ligands by amide bond formation

Seven phosphane-functionalized deoxyuridines have been prepared by amide bond formation between aminodeoxyuridines and phosphanylcarboxylic acids. X-ray crystal structures for two of these new modified nucleosides have been obtained. The same coupling method has been extended to oligonucleotides. The phosphane containing strands have been purified and characterized by MALDI-TOF and, for the first time, 31P NMR spectrometry. Coordination of a phosphane-modified 15-mer to a [PdCl(η3-allyl)] moiety has been confirmed by 31P NMR spectroscopy.

Ru-labeled oligonucleotides for photoinduced reactions on targeted DNA guanines

As a strategy to synthesize new sequence-specific DNA photoreagents, oligodeoxyribonucleotides bearing a photoreactive [RuII(tap)2(dip)]2+ complex (tap = 1,4,5,8-tetraazaphenanthrene; dip = 4,7-diphenylphenanthroline) teth