21017-05-0

Basic information

• Product Name: 5'-CHLORO-5'-DEOXYINOSINE
• Synonyms: 5'-CHLORO-5'-DEOXYINOSINE
• CAS NO: 21017-05-0
• Molecular Formula: C10H11ClN4O4
• Molecular Weight: 286.67
• Mol File: 21017-05-0.mol

Chemical Properties

• Melting Point: 180 °C (decomp)
• Boiling Point: 639.1 °C at 760 mmHg
• Flash Point: 340.3 °C
• Appearance: /
• Density: 2.03 g/cm³
• Vapor Pressure: 3.29E-17mmHg at 25°C
• Refractive Index: 1.846
• PKA: 8.92±0.70(Predicted)
• CAS DataBase Reference: 5'-CHLORO-5'-DEOXYINOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-CHLORO-5'-DEOXYINOSINE(21017-05-0)
• EPA Substance Registry System: 5'-CHLORO-5'-DEOXYINOSINE(21017-05-0)

Safety Data

• Hazardous Substances Data: 21017-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
5'-Chloro-5'-deoxyinosine is utilized as a precursor in the synthesis of nucleic acid analogs, which are essential for developing new therapeutic agents. Its unique structure aids in exploring the structure-activity relationships of nucleosides, potentially leading to the discovery of novel treatments.
Used in Research:
As a research tool, 5'-Chloro-5'-deoxyinosine is employed to study the effects of chlorine substitution on the structure and function of nucleosides. This helps scientists understand how such modifications can influence the properties and potential applications of nucleoside-based compounds in various fields, including medicine and biotechnology.

InChI:InChI=1/C10H11ClN4O4/c11-1-4-6(16)7(17)10(19-4)15-3-14-5-8(15)12-2-13-9(5)18/h2-4,6-7,10,16-17H,1H2,(H,12,13,18)/t4-,6-,7-,10-/m1/s1

Upstream product

• 58-63-9 Inosine 
• 892-48-8 5'-deoxy-5'-chloroadenosine 
• 662131-88-6 5'-chloro-5'-deoxy-2',3'-O-sulfinyladenosine 

Relevant articles and documents

Adenylate Deaminase (5′-Adenylic Acid Deaminase, AMPDA)-Catalyzed Deamination of 5′-Deoxy-5′-Substituted and 5′-Protected Adenosines: A Comparison with the Catalytic Activity of Adenosine Deaminase (ADA)

The enzyme adenylate deaminase (AMPDA) is able to catalyze the hydrolytic deamination of 5′-substituted and 5′-protected 5′ -deoxyadenosines, whereas limited or no activity is shown by adenosine deaminase (ADA) towards the same substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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

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.

Preparation method of 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose

The invention discloses a preparation method of 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose, and belongs to the field of nucleoside synthesis in organic chemistry. The method comprises reaction steps asfollows: inosine 1 and triphenyl phosphite-halogen are subjected to a reaction, and a compound 2 is obtained; then the compound 2 is subjected to hydrogenation reduction under palladium/carbon catalysis; an obtained compound 3 is subjected to a reaction in acetic anhydride under catalysis of inorganic boric acid, and 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribose is obtained. The synthesis method adoptscheap raw materials and short steps and has industrial application prospect, and industrial production is easy.

The fluorinase from Streptomyces cattleya is also a chlorinase

(Chemical Equation Presented) Choices choices: The fluorinase enzyme from Streptomyces cattleya (catalyzes the formation of a C-F bond from fluoride ions) also has the capacity to utilize a chloride ion although it has a clear preference for the fluoride ion. The enzyme mediates a nucleophilic chlorination reaction, which is an unusual mechanism for enzymatic chlorination.