CAS 5856-48-4

2′,3′-O-(1-Methylethylidene)-6-thioinosine

Description:

2′,3′-O-(1-Methylethylidene)-6-thioinosine is a modified nucleoside that features a thio group at the 6-position of the purine base, which is characteristic of certain nucleoside analogs. This compound is notable for its structural modifications that enhance its stability and biological activity compared to natural nucleosides. The presence of the 1-methylethylidene group at the 2′ and 3′ positions contributes to its resistance to enzymatic degradation, making it of interest in medicinal chemistry and biochemistry. Such modifications can influence the compound's interaction with nucleic acid targets, potentially affecting its role in cellular processes or therapeutic applications. Additionally, the thio substitution may impart unique properties, such as altered binding affinities or enhanced antiviral activity. Overall, 2′,3′-O-(1-Methylethylidene)-6-thioinosine exemplifies the diverse strategies employed in the design of nucleoside analogs for research and therapeutic purposes.

Formula: C₁₃H₁₆N₄O₄S

InChI: InChI=1S/C13H16N4O4S/c1-13(2)20-8-6(3-18)19-12(9(8)21-13)17-5-16-7-10(17)14-4-15-11(7)22/h4-6,8-9,12,18H,3H2,1-2H3,(H,14,15,22)/t6-,8-,9-,12-/m1/s1

InChI key: InChIKey=HXZCOKXEDYVENB-WOUKDFQISA-N

SMILES: C(O)[C@H]1O[C@H]([C@]2([C@@]1(OC(C)(C)O2)[H])[H])N3C4=C(N=C3)C(=S)N=CN4

Synonyms:

• 2',3'-O-Isopropylidene-6-thioinosine
• 2′,3′-O-(1-Methylethylidene)-6-thioinosine
• 2′,3′-O-Isopropylidene-6-mercaptopurine riboside
• 2′,3′-O-Isopropylidene-6-thioinosine
• 9-[2,3-O-(1-methylethylidene)pentofuranosyl]-3,9-dihydro-6H-purine-6-thione
• 9H-Purine-6(1H)-thione, 9-(2,3-O-isopropylidene-β-<span class="text-smallcaps">D</span>-ribofuranosyl)-
• Furo[3,4-d]-1,3-dioxole, inosine deriv.
• Inosine, 2′,3′-O-(1-methylethylidene)-6-thio-
• NSC 27305
• 9H-Purine-6(1H)-thione, 9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-

9-((3AR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3,9-dihydro-6H-purine-6-thione

CAS: 5856-48-4

Formula: C₁₃H₁₆N₄O₄S

Purity: 95%

Color and Shape: Solid

Molecular weight: 324.3555

Ref: IN-DA00EC86

6-Mercapto-9-(2,3-O-isopropylidine-b-D-ribofuranosyl)purine

CAS: 5856-48-4

Formula: C₁₃H₁₆N₄O₄S

Molecular weight: 324.36

Ref: 7W-GN1346

2',3'-O-Isopropylidene-6-mercaptopurine riboside

CAS: 5856-48-4

2',3'-O-Isopropylidene-6-mercaptopurine riboside

Purity: 98%

Molecular weight: 324.36g/mol

Ref: 54-OR1007248

2',3'-O-Isopropylidene-6-thioinosine

Controlled Product

CAS: 5856-48-4

Applications 2',3'-O-Isopropylidene-6-thioinosine is an intermediate in the synthesis of protein-reactive ATP analogs for affinity labeling.
References Faust, U., et al.: Eur. J. Biochem., 43, 273 (1974);

Formula: C₁₃H₁₆N₄O₄S

Color and Shape: Neat

Molecular weight: 324.36

Ref: TR-I825480

2',3'-O-Isopropylidene-6-thioinosine

CAS: 5856-48-4

2',3'-O-Isopropylidene-6-thioinosine is a fluorinated analogue of 6-thioguanine, which is an important precursor in the synthesis of nucleotides. The compound contains a fluorine atom at the 2' position and a sulfur atom at the 3' position of the ribose ring. It is soluble in organic solvents and can be used as a tracer for biochemical studies. The thermal stability of 2',3'-O-Isopropylidene-6-thioinosine has been demonstrated by molecular modelling and thermally induced filtration experiments. Molecular modeling has also shown that 2',3'-O-Isopropylidene-6-thioinosine binds to the active site of uridine phosphorylase, which is involved in pyrimidine salvage pathways in cells.
2',3'-O-Isopropylidene-6-thioinos

Formula: C₁₃H₁₆N₄O₄S

Purity: Min. 95%

Molecular weight: 324.36 g/mol

Ref: 3D-NI08025