Category: 1192027-04-5

O’Shea, Jonathan published the artcileAn efficient deprotection method for 5′-[O,O-bis(pivaloyloxymethyl)]-(E)-vinylphosphonate containing oligonucleotides, Safety of N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, the publication is Tetrahedron (2018), 74(42), 6182-6186, database is CAplus.

5′-(E)-Vinylphosphonate (VP) is an effective bioisostere of the natural 5′-monophosphate in small interfering RNAs (siRNAs). Solid-phase synthesis of VP-siRNAs requires the use of appropriately protected VP-phosphoramidites in combination with optimal oligonucleotide deprotection conditions. Addition of 3% (v) neat diethylamine to the standard aqueous ammonia deprotection conditions allows clean and rapid one-step deprotection of 5′-[O,O-bis(pivaloyloxymethyl)] (POM)-protected VP oligonucleotides, minimizing side reactions and impurities, which broadly enhances the scope of VP oligonucleotide synthesis.

Tetrahedron published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C5H7N3S3, Safety of N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Karskela, Marika published the artcileSynthesis and Cellular Uptake of Fluorescent Labeled Multivalent Hyaluronan Disaccharide Conjugates of Oligonucleotide Phosphorothioates, HPLC of Formula: 1192027-04-5, the publication is Bioconjugate Chemistry (2008), 19(12), 2549-2558, database is CAplus and MEDLINE.

Clustered hyaluronan disaccharides were studied as mediators of cellular delivery of antisense oligonucleotides through receptor-mediated endocytosis. For this purpose, a synthetic route for preparation of an appropriately protected hyaluronic acid dimer bearing an aldehyde tether I was devised. Up to three non-nucleosidic phosphoramidite building blocks, each bearing two phthaloyl protected aminooxy groups, were then inserted into the 3′-terminus of the desired phosphorothioate oligodeoxyribonucleotide, and 6-FAM phosphoramidite was introduced into the 5′-terminus. After completion of the chain assembly, the aldehyde-tethered sugar ligands were attached to the deprotected aminooxy functions by on-support oximation. Three fluorescein-labeled phosphorothioate oligonucleotide glycoconjugates containing two, four, or six hyaluronan disaccharides were prepared The influence of the hyaluronan moieties on the cellular uptake of the thiolated oligonucleotides was tested in a cell line expressing the hyaluronan receptor CD44. Specific uptake was not detected with this combination of multiple hyaluronan disaccharides.

Bioconjugate Chemistry published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C5H7N3S3, HPLC of Formula: 1192027-04-5.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Yang, Jimin published the artcileSolid-Phase Synthesis of Phosphorothioate Oligonucleotides Using Sulfurization Byproducts for in Situ Capping, Category: thiazole, the publication is Journal of Organic Chemistry (2018), 83(19), 11577-11585, database is CAplus and MEDLINE.

Phosphorothioate (PS) oligonucleotides are manufactured via a solid-phase chain elongation process in which a four-reaction cycle consisting of detritylation, coupling, sulfurization, and failure sequence capping with Ac₂O is repeated. In the capping step uncoupled sequences are acetylated at the 5′-OH to stop the chain growth and control the levels of deletion, or (n-1), impurities. Herein, we report that the byproducts of the commonly used sulfurization reagents react with the 5′-OH and cap the failure sequences. The standard Ac₂O capping step can therefore be eliminated and this 3-reaction cycle process affords higher yield and higher or comparable overall purity compared to the conventional 4-reaction synthesis. This improvement results in reducing the number of reactions from âˆ?0 to âˆ?0 for synthesis of a typical length 20-mer oligonucleotide. For every kilogram of an oligonucleotide intermediate synthesized, > 500 L of reagents and organic solvents are saved and the E-factor is decreased to < 1500 from âˆ?000.

Journal of Organic Chemistry published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C12H15ClO3, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Guzaev, Andrei P. published the artcileReactivity of 3H-1,2,4-dithiazole-3-thiones and 3H-1,2-dithiole-3-thiones as sulfurizing agents for oligonucleotide synthesis, Related Products of thiazole, the publication is Tetrahedron Letters (2011), 52(3), 434-437, database is CAplus.

The reactivity of 5-amino-3H-1,2,4-dithiazole-3-thiones substituted at their amino group and 5-amino-3H-1,2-dithiole-3-thiones substituted at their amino group and C4 toward compounds containing P(III) atoms has been studied. N,N-Di-substituted-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)methanimidamides were selected as novel efficient sulfur transfer reagents suitable for DNA and RNA synthesis.

Tetrahedron Letters published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C5H7N3S3, Related Products of thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Yanachkov, Ivan published the artcileSelf-neutralizing oligonucleotides with enhanced cellular uptake, Product Details of C5H7N3S3, the publication is Organic & Biomolecular Chemistry (2017), 15(6), 1363-1380, database is CAplus and MEDLINE.

There is tremendous potential for oligonucleotide (ON) therapeutics, but low cellular penetration due to their polyanionic nature is a major obstacle. We addressed this problem by developing a new approach for ON charge neutralization in which multiple branched charge-neutralizing sleeves (BCNSs) are attached to the internucleoside phosphates of ON by phosphotriester bonds. The BCNSs are terminated with pos. charged amino groups, and are optimized to form ion pairs with the neighboring phosphate groups. The new modified ONs can be prepared by standard automated phosphoramidite chem. in good yield and purity. They possess good solubility and hybridization properties, are not involved in non-standard intramol. aggregation, have low cytotoxicity, adequate chem. stability, improved serum stability, and above all, display significantly enhanced cellular uptake. Thus, the new ON derivatives exhibit properties that make them promising candidates for the development of novel therapeutics or research tools for modulation of the expression of target genes.

Organic & Biomolecular Chemistry published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C8H5IO, Product Details of C5H7N3S3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Lartia, Remy published the artcileVersatile Introduction of Azido Moiety into Oligonucleotides through Diazo Transfer Reaction, HPLC of Formula: 1192027-04-5, the publication is Organic Letters (2011), 13(20), 5672-5675, database is CAplus and MEDLINE.

The use of a diazo transfer (DZT) reagent enables clean and efficient conversion of amino oligodeoxyribonucleotides (ODNs) into their azido counterparts under mild conditions. ODNs bearing an amino tether at the 3′, 5′, or any internal position could be modified in this manner thus demonstrating the versatility of this reaction. Easy access to such azido-modified ODNs is of great interest for conjugation in particular through click’ copper catalyzed 1,3-dipolar cycloaddition (CuAAC reaction).

Organic Letters published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C5H7N3S3, HPLC of Formula: 1192027-04-5.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Li, M. published the artcileSynthesis and cellular activity of stereochemically-pure 2′-O-(2-methoxyethyl)-phosphorothioate oligonucleotides, Category: thiazole, the publication is Chemical Communications (Cambridge, United Kingdom) (2017), 53(3), 541-544, database is CAplus and MEDLINE.

Stereochem.-pure 2′-O-(2-methoxyethyl)-phosphorothioate (PS-MOE) oligonucleotides were synthesized from new chiral oxazaphospholidine-containing nucleosides. Thermal stability studies showed that the incorporation of Rp-PS linkages increased RNA-binding affinity. In cells, a full Rp-PS-MOE splice-switching oligonucleotide targeting part of the ferrochelatase gene was more potent than its Sp-PS counterpart, but of similar potency to the stereo-random PS-parent sequence.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C5H7N3S3, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wang, Ning published the artcileStudy on synthesis of new-sulfurizing reagent DDTT, SDS of cas: 1192027-04-5, the publication is Huaxue Shijie (2013), 54(12), 734-736, 739, database is CAplus.

((Dimethylamino-methylidene)amino)-3H-1,2,4-dithiazoline-3-thione was synthesized from 5-amino-3H-1,2,4-dithiazole-3-thione (xanthane hydride) using THF as solvent. The exptl. results showed that the optimum conditions were as follows: the molar ratio was 1:1.1, the reaction temperature was 25°C and the reaction time was 6 h. The yield was 90%. Convenient operation of the process, easy of the product purification up, high yield and low pollution show that the process is suitable for industrial production, and it opens wide prospects for market application.

Huaxue Shijie published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C48H47FeP, SDS of cas: 1192027-04-5.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica