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5'-CHLORO-5'-DEOXYADENOSINE is a chemical compound that serves as an intermediate in the synthesis of 5'-Deoxy-5'-(methylthio)adenosine (D242600). It is utilized for studying the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP), a tumor suppressor gene expressed enzyme that plays a crucial role in the S-adenosylmethionine (AdoMet) and methionine salvage pathways.

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  • 892-48-8 Structure
  • Basic information

    1. Product Name: 5'-CHLORO-5'-DEOXYADENOSINE
    2. Synonyms: 5'-CHLORO-5'-DEOXYADENOSINE;5-CHLORO-5-DEOXYADENOSINE HYDRATE;5'-CHLORO-5'-DEOXYADENOSINE MONOHYDRATE;5’-chloro-5’-deoxy-adenosin;5'-CHLORO-5'-DEOXY-D-ADENOSINE;5'-Deoxy-5'-chloroadenosine;5'-Cl-5'-deoxyadenosine;Adenosine,5'-chloro-5'-deoxy-
    3. CAS NO:892-48-8
    4. Molecular Formula: C10H12ClN5O3
    5. Molecular Weight: 285.69
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 892-48-8.mol
  • Chemical Properties

    1. Melting Point: 187 °C (exothermic decomp onset @144.5 C)(lit.)
    2. Boiling Point: 645.6 °C at 760 mmHg
    3. Flash Point: 344.2 °C
    4. Appearance: /
    5. Density: 2.03g/cm3
    6. Vapor Pressure: 1.5E-17mmHg at 25°C
    7. Refractive Index: 1.87
    8. Storage Temp.: 2-8°C
    9. Solubility: DMSO (Slightly), Water (Slightly, Heated)
    10. PKA: 13.03±0.70(Predicted)
    11. CAS DataBase Reference: 5'-CHLORO-5'-DEOXYADENOSINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 5'-CHLORO-5'-DEOXYADENOSINE(892-48-8)
    13. EPA Substance Registry System: 5'-CHLORO-5'-DEOXYADENOSINE(892-48-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS: AU7357200
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 892-48-8(Hazardous Substances Data)

892-48-8 Usage

Uses

Used in Pharmaceutical Research:
5'-CHLORO-5'-DEOXYADENOSINE is used as a research intermediate for the synthesis of 5'-Deoxy-5'-(methylthio)adenosine (D242600). 5'-CHLORO-5'-DEOXYADENOSINE is essential for investigating the properties and functions of 5′-methylthioadenosinephosphorylase (MTAP), an enzyme involved in tumor suppression and the regulation of vital metabolic pathways.
Used in Enzyme Studies:
In the field of biochemistry, 5'-CHLORO-5'-DEOXYADENOSINE is employed as a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP). Understanding the enzyme's behavior and its role in the AdoMet and methionine salvage pathways can provide insights into the development of potential therapeutic agents targeting cancer and other diseases.
Used in Cancer Research:
5'-CHLORO-5'-DEOXYADENOSINE contributes to cancer research by enabling the study of MTAP, a tumor suppressor gene expressed enzyme. Investigating the enzyme's function and its impact on cancer development can lead to the discovery of novel cancer treatments and therapeutic strategies.
Used in Metabolic Pathway Analysis:
5'-CHLORO-5'-DEOXYADENOSINE is utilized in the analysis of the S-adenosylmethionine (AdoMet) and methionine salvage pathways, which are essential for various cellular processes, including DNA methylation, protein synthesis, and polyamine biosynthesis. Understanding these pathways can help researchers develop targeted therapies for various diseases, including cancer.

Check Digit Verification of cas no

The CAS Registry Mumber 892-48-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,9 and 2 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 892-48:
(5*8)+(4*9)+(3*2)+(2*4)+(1*8)=98
98 % 10 = 8
So 892-48-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H12ClN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)

892-48-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 5'-chloro-5'-deoxyadenosine

1.2 Other means of identification

Product number -
Other names (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(chloromethyl)oxolane-3,4-diol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:892-48-8 SDS

892-48-8Relevant articles and documents

Synthesis and characterization of Se-adenosyl-L-selenohomocysteine selenoxide

Duclos, Richard I.,Cleary, Dillon C.,Catcott, Kalli C.,Zhou, Zhaohui Sunny

, p. 135 - 144 (2015)

Selenium is an essential micronutrient in humans due to the important roles of the selenocysteine-containing selenoproteins. Organoselenium metabolites are generally found to be substrates for the biochemical pathways of their sulfur analogs, and the redox chemistry of selenomethionine and some other metabolites have been previously reported. We now report the first synthesis and characterization of Se-adenosylselenohomocysteine selenoxide (SeAHO) prepared via hydrogen peroxide oxidation of Se-adenosylselenohomocysteine. The selenoxide SeAHO, in contrast to its corresponding sulfoxide S-adenosylhomocysteine (SAHO), can form hydrate, has an electrostatic interaction between the α-amino acid moiety and the highly polar selenoxide functional group, and readily oxidizes glutathione (GSH) and cysteine thiols.

Discovery of a dual PRMT5-PRMT7 inhibitor

Smil, David,Eram, Mohammad S.,Li, Fengling,Kennedy, Steven,Szewczyk, Magdalena M.,Brown, Peter J.,Barsyte-Lovejoy, Dalia,Arrowsmith, Cheryl H.,Vedadi, Masoud,Schapira, Matthieu

, p. 408 - 412 (2015)

The protein arginine methyltransferases PRMT7 and PRMT5, respectively, monomethylate and symmetrically dimethylate arginine side-chains of proteins involved in diverse cellular mechanisms, including chromatin-mediated control of gene transcription, splicing, and the RAS to ERK transduction cascade. It is believed that PRMT5 and PRMT7 act in conjunction to methylate their substrates, and genetic deletions support the notion that these enzymes derepress cell proliferation and migration in cancer. Using available structures of PRMT5, we designed DS-437, a PRMT5 inhibitor with an IC50 value of 6 μM against both PRMT5 and PRMT7 that is inactive against 29 other human protein-, DNA-, and RNA-methyltransferases and inhibits symmetrical dimethylation of PRMT5 substrates in cells. This compound behaves as a cofactor competitor and represents a valid scaffold to interrogate the potential of the PRMT5-PRMT7 axis as a target for therapy.

Directed Evolution of a Fluorinase for Improved Fluorination Efficiency with a Non-native Substrate

Sun, Huihua,Yeo, Wan Lin,Lim, Yee Hwee,Chew, Xinying,Smith, Derek John,Xue, Bo,Chan, Kok Ping,Robinson, Robert C.,Robins, Edward G.,Zhao, Huimin,Ang, Ee Lui

, p. 14277 - 14280 (2016)

Fluorinases offer an environmentally friendly alternative for selective fluorination under mild conditions. However, their diversity is limited in nature and they have yet to be engineered through directed evolution. Herein, we report the directed evolution of the fluorinase FlA1 for improved conversion of the non-native substrate 5′-chloro-5′-deoxyadenosine (5′-ClDA) into 5′-fluoro-5′-deoxyadenosine (5′-FDA). The evolved variants, fah2081 (A279Y) and fah2114 (F213Y, A279L), were successfully applied in the radiosynthesis of 5′-[18F]FDA, with overall radiochemical conversion (RCC) more than 3-fold higher than wild-type FlA1. Kinetic studies of the two-step reaction revealed that the variants show a significantly improved kcatvalue in the conversion of 5′-ClDA into S-adenosyl-l-methionine (SAM) but a reduced kcatvalue in the conversion of SAM into 5′-FDA.

Potent SARS-CoV-2 mRNA Cap Methyltransferase Inhibitors by Bioisosteric Replacement of Methionine in SAM Cosubstrate

Bobi?eva, Olga,Bobrovs, Raitis,Ka?epe, Iveta,Patetko, Liene,Kalni??, Gints,?i?ovs, Mihails,Bula, Anna L.,Grī Nberga, Solveiga,Borodu??is, Mā Rti??,Ramata-Stunda, Anna,Rostoks, Nils,Jirgensons, Aigars,Tā Rs, Kaspars,Jaudzems, Kristaps

, p. 1102 - 1107 (2021/06/30)

Viral mRNA cap methyltransferases (MTases) are emerging targets for the development of broad-spectrum antiviral agents. In this work, we designed potential SARS-CoV-2 MTase Nsp14 and Nsp16 inhibitors by using bioisosteric substitution of the sulfonium and amino acid substructures of the cosubstrate S-adenosylmethionine (SAM), which serves as the methyl donor in the enzymatic reaction. The synthetically accessible target structures were prioritized using molecular docking. Testing of the inhibitory activity of the synthesized compounds showed nanomolar to submicromolar IC50 values for five compounds. To evaluate selectivity, enzymatic inhibition of the human glycine N-methyltransferase involved in cellular SAM/SAH ratio regulation was also determined, which indicated that the discovered compounds are nonselective inhibitors of the studied MTases with slight selectivity for Nsp16. No cytotoxic effects were observed; however, this is most likely a result of the poor cell permeability of all evaluated compounds.

Synthesis of triazole-linked SAM-adenosine conjugates: Functionalization of adenosine at N-1 or N-6 position without protecting groups

Atdjian, Colette,Braud, Emmanuelle,Coelho, Dylan,Ethève-Quelquejeu, Mélanie,Iannazzo, Laura

, (2020/08/07)

More than 150 RNA chemical modifications have been identified to date. Among them, methylation of adenosine at the N-6 position (m6A) is crucial for RNA metabolism, stability and other important biological events. In particular, this is the most abundant

5'-Deoxidation-5'-isopropyl-substituted-amino nucleoside compound and preparing method and application thereof

-

Paragraph 0325-0329, (2019/05/28)

The invention discloses a 5'-deoxidation-5'-isopropyl-substituted-amino nucleoside compound shown in a formula 7, a preparing method of the compound shown in the formula 7 and application of the compound shown in the formula 7 to preparing a 5'-deoxidation-5'-polysubstitution amino nucleoside compound 1 as a midbody. The formula is defined in the description.

S-Adenosyl Methionine Cofactor Modifications Enhance the Biocatalytic Repertoire of Small Molecule C-Alkylation

McKean, Iain J. W.,Sadler, Joanna C.,Cuetos, Anibal,Frese, Amina,Humphreys, Luke D.,Grogan, Gideon,Hoskisson, Paul A.,Burley, Glenn A.

supporting information, p. 17583 - 17588 (2019/11/11)

A tandem enzymatic strategy to enhance the scope of C-alkylation of small molecules via the in situ formation of S-adenosyl methionine (SAM) cofactor analogues is described. A solvent-exposed channel present in the SAM-forming enzyme SalL tolerates 5′-chloro-5′-deoxyadenosine (ClDA) analogues modified at the 2-position of the adenine nucleobase. Coupling SalL-catalyzed cofactor production with C-(m)ethyl transfer to coumarin substrates catalyzed by the methyltransferase (MTase) NovO forms C-(m)ethylated coumarins in superior yield and greater substrate scope relative to that obtained using cofactors lacking nucleobase modifications. Establishing the molecular determinants that influence C-alkylation provides the basis to develop a late-stage enzymatic platform for the preparation of high value small molecules.

Purine compound containing bicyclic group, and preparation method thereof

-

Paragraph 0208; 0212, (2019/10/01)

The invention provides a purine compound containing a bicyclic group which is shown as a formula (I) and a formula (II) and a pharmaceutically acceptable salt, and a preparation method thereof. The compound is an inhibitor of histone methyltransferase DOT1L, and can be used for treating diseases caused by the abnormity of enzyme activity, such as tumor.

Convenient preparation of pinometostat and related 5′-deoxy-5′-amino adenosine derivatives as well as their activity against DOT1L

Liu, Tongchao,Ren, Huanming,Li, Cong,Chen, Guohua,Cheng, Maosheng,Zhao, Dongmei,Shen, Jingkang,Li, Jia,Zhou, Yubo,Xiong, Bing,Chen, Yue-Lei

, p. 415 - 417 (2018/01/10)

From adenosine and 2′-C-Me adenosine, a 3-step route towards nucleoside DOT1L inhibitors, including pinometostat, EPZ5677, and FED1, was established. With useful structural-activity relationship information, the newly prepared 2′-C-Me adenosine derivative

SELECTIVE INHIBITORS OF PROTEIN ARGININE METHYLTRANSFERASE 5 (PRMT5)

-

, (2018/01/20)

The disclosure is directed to compounds of Formula (I) and Formula (II). Methods of their use and preparation is other described.

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