4754-39-6

Basic information

• Product Name: 5'-DEOXYADENOSINE
• Synonyms: 5'-DEOXYADENOSINE;5’-deoxy-adenosin;(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-5-methyl-oxolane-3,4-diol;6-Amino-9-(5-deoxy-β-D-ribofuranosyl)-9H-purine;9-(5-Deoxy-β-D-ribofuranosyl)-9H-purine-6-amine;Adenosine, 5'-deoxy-;5′-dAdo
• CAS NO: 4754-39-6
• Molecular Formula: C₁₀H₁₃N₅O₃
• Molecular Weight: 251.24
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 4754-39-6.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 595°Cat760mmHg
• Flash Point: 313.6°C
• Appearance: /
• Density: 1.93g/cm³
• Vapor Pressure: 5.29E-15mmHg at 25°C
• Refractive Index: 1.867
• Storage Temp.: 2-8°C
• PKA: 13.29±0.70(Predicted)
• CAS DataBase Reference: 5'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-DEOXYADENOSINE(4754-39-6)
• EPA Substance Registry System: 5'-DEOXYADENOSINE(4754-39-6)

Safety Data

• WGK Germany: 3
• RTECS: AU7358650
• Hazardous Substances Data: 4754-39-6(Hazardous Substances Data)

Usage

Description

5'-Deoxyadenosine, also known as Cordycepin, is an oxidized nucleoside found in the urine of normal subjects. It is a 5'-deoxyribonucleoside compound with adenosine as the nucleobase. Oxidized nucleosides, like 5'-Deoxyadenosine, serve as excellent biomarkers for assessing the extent of damage to genetic material. This has been a significant area of interest in understanding the mechanisms behind aging, neurodegenerative diseases, and carcinogenesis.

Uses

Used in Mass Spectrometry:
5'-Deoxyadenosine is utilized as a standard in mass spectroscopy, a technique used to identify and quantify compounds based on their mass-to-charge ratio. It helps in providing accurate measurements and comparisons for various samples.
Used in Enzyme Activity Screening:
5'-Deoxyadenosine is employed as an inhibitor for screening thymidine phosphorylase activity. Thymidine phosphorylase is an enzyme involved in the salvage pathway of pyrimidine synthesis, and its activity can be crucial in certain biological processes and disease states.
Used in Enzyme Assays:
5'-Deoxyadenosine is used as a substrate in the 5'-Deoxyadenosine deaminase (DadD) assay. DadD is an enzyme that catalyzes the deamination of 5'-deoxyadenosine to inosine, which is an essential step in the regulation of nucleotide metabolism. The assay helps in studying the enzyme's function and its role in various biological processes.

Biochem/physiol Actions

5′-Deoxyadenosine is a substrate for the enzyme methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase in microbes. 5′-Deoxyadenosine is a byproduct of cleavage of S-adenosylmethionine (SAM). High levels of 5′-Deoxyadenosine inhibits SAM dependent enzymes. It also inhibits biotin synthase (BioB) and lipoyl synthase (LipA) enzymes.

InChI:InChI=1/C10H13N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H3,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

Upstream product

• 892-48-8 5'-deoxy-5'-chloroadenosine 
• 110022-91-8 di-O-acetyl-5-deoxy-ξ-D-ribofuranosyl chloride 
• 14031-35-7 S-Adenosyl-L-methionine 
• 60-18-4 L-tyrosine 
• 202407-26-9 ¹³C₉-¹⁵N-L-tyrosine 
• 24346-00-7 SAM-Cl 
• 13291-74-2 gentamicin A 
• 485-80-3 S-adenosyl-L-methionine 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 
• 4005-49-6 N-benzoyladenine 
• 53199-56-7 S-adenosyl-L-homocysteine sulfone 
• 21127-35-5 S-adenosylselenohomocysteine selenoxide 
• 785816-21-9 C₈H₁₃⁽²⁾HN₃O₇P 

Downstream Products

• 66224-66-6 adenine 
• 1237496-74-0 1-(3-methyl-2-butenylamino)-9-(5'-deoxy-β-D-ribofuranosyl)purine hydrobromide 
• 13039-75-3 5′-deoxyribose 
• 1000003-70-2 C₃₈H₂₉N₅O₇ 
• 4680-63-1 2-amino-9-(5-deoxy-β-D-ribofuranosyl)-9H-6-thiopurine 
• 63734-70-3 8-bromo-5'-deoxy-adenosine 

Relevant articles and documents

Syntheses of potential antimetabolites. XV. Syntheses of a sulfonate analog of adenosine 5' phosphate and an alternative synthesis of 5', 8 S anhydroadenine nucleosides and 5' deoxyspongoadenosine and its isomers

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Identification and characterization of functional homologs of nitrogenase cofactor biosynthesis protein NifB from methanogens

Nitrogenase biosynthesis protein NifB catalyzes the radical S-adenosyl-L-methionine (SAM)-dependent insertion of carbide into the M cluster, the cofactor of the molybdenum nitrogenase from Azotobacter vinelandii. Here, we report the identification and characterization of two naturally €truncated€ homologs of NifB from Methanosarcina acetivorans (NifBMa) and Methanobacterium thermoautotrophicum (NifBMt), which contain a SAM-binding domain at the N terminus but lack a domain toward the C terminus that shares homology with NifX, an accessory protein in M cluster biosynthesis. NifBMa and NifBMt are monomeric proteins containing a SAM-binding [Fe4S4] cluster (designated the SAM cluster) and a [Fe4S4]-like cluster pair (designated the K cluster) that can be processed into an [Fe8S9] precursor to the M cluster (designated the L cluster). Further, the K clusters in NifBMa and NifBMt can be converted to L clusters upon addition of SAM, which corresponds to their ability to heterologously donate L clusters to the biosynthetic machinery of A. vinelandii for further maturation into the M clusters. Perhaps even more excitingly, NifBMa and NifBMt can catalyze the removal of methyl group from SAM and the abstraction of hydrogen from this methyl group by 5€-deoxyadenosyl radical that initiates the radical-based incorporation of methyl-derived carbide into the M cluster. The successful identification of NifBMa and NifBMt as functional homologs of NifB not only enabled classification of a new subset of radical SAM methyltransferases that specialize in complex metallocluster assembly, but also provided a new tool for further characterization of the distinctive, NifB-catalyzed methyl transfer and conversion to an iron-bound carbide.

The B12-independent glycerol dehydratase activating enzyme from Clostridium butyricum cleaves SAM to produce 5′-deoxyadenosine and not 5′-deoxy-5′-(methylthio)adenosine

Glycerol dehydratase activating enzyme (GD-AE) is a radical S-adenosyl-L-methionine (SAM) enzyme that installs a catalytically essential amino acid backbone radical onto glycerol dehydratase in bacteria under anaerobic conditions. Although GD-AE is closely homologous to other radical SAM activases that have been shown to cleave the S-C(5′) bond of SAM to produce 5′-deoxyadenosine (5’-dAdoH) and methionine, GD-AE from Clostridium butyricum has been reported to instead cleave the S-C(γ) bond of SAM to yield 5′-deoxy-5′-(methylthio)adenosine (MTA). Here we re-investigate the SAM cleavage reaction catalyzed by GD-AE and show that it produces the widely observed 5’-dAdoH, and not the less conventional product MTA.

HygY Is a Twitch Radical SAM Epimerase with Latent Dehydrogenase Activity Revealed upon Mutation of a Single Cysteine Residue

HygY is a SPASM/twitch radical SAM enzyme hypothesized to catalyze the C2′-epimerization of galacamine during the biosynthesis of hygromycin B. This activity is confirmed via biochemical and structural analysis of the derivatized reaction products using chemically synthesized deuterated substrate, high-resolution mass spectrometry and1H NMR. Electron paramagnetic resonance spectroscopy of the reduced enzyme is consistent with ligation of two [Fe4S4] clusters characteristic of the twitch radical SAM subgroup. HygY catalyzed epimerization proceeds with incorporation of a single solvent Hydron into the talamine product facilitated by the catalytic cysteine-183 residue. Mutation of this cysteine to alanine converts HygY from a C2′-epimerase to an C2′-dehydrogenase with comparable activity. The SPASM/twitch radical SAM enzymes often serve as anaerobic oxidases making the redox-neutral epimerases in this class rather interesting. The discovery of latent dehydrogenase activity in a twitch epimerase may therefore offer new insights into the mechanistic features that distinguish oxidative versus redox-neutral SPASM/twitch enzymes and lead to the evolution of new enzyme activities.