14719-21-2

Usage

Uses

Used in Diagnostic Applications:
Acetamide, 2,2,2-trifluoro-N-2-propynylis used as an intermediate in the synthesis of Texas Red-5-dUTP (T320100), a fluorescence-labelled nucleotide analog. Texas Red-5-dUTP is utilized diagnostically for the detection of rearranged SS18 in formalin-fixed, paraffin-embedded synovial sarcoma. The compound's unique structure allows for the development of sensitive and specific diagnostic tools in the field of medical research and pathology.

Upstream product

• 407-25-0 trifluoroacetic anhydride 
• 2450-71-7 Propargylamine 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 114748-58-2 5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxycytidine 
• 114748-60-6 5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxy-uridine 
• 114748-71-9 7-deaza-2',3'-dideoxy-7-(3-trifluoroacetamidopropyn-1-yl)adenosine 
• 114748-68-4 N-{3-[2-Amino-7-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide 
• 114748-68-4 N-{3-[2-Amino-4-hydroxy-7-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide 
• 130532-28-4 4-Methyl-benzoic acid (2S,5R)-5-{4-hydroxy-2-oxo-5-[3-(2,2,2-trifluoro-acetylamino)-prop-1-ynyl]-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 
• 114748-60-6 2,2,2-Trifluoro-N-{3-[1-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-prop-2-ynyl}-acetamide 
• 114748-58-2 N-{3-[4-Amino-1-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide 
• 115899-38-2 N-{3-[4-Amino-1-((4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide 
• 114748-71-9 N-{3-[4-Amino-7-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide 
• 114748-68-4 N-{3-[2-Amino-7-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide 
• 120016-97-9 5-(3-trifluoroacetamidopropargyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine 
• 178420-75-2 7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[3-(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 260397-83-9 2-tert-butoxycarbonylamino-3-{4-[3-(2,2,2-trifluoro-acetylamino)-prop-1-ynyl]-phenyl}-propionic acid 

Relevant academic research and scientific papers

Aptamer-based proximity labeling guides covalent RNA modification

We describe the development of a proximity-induced bio-orthogonal inverse electron demand Diels-Alder reaction that exploits the high-affinity interaction between a dienophile-modified RhoBAST aptamer and its tetramethyl rhodamine methyltetrazine substrate. We applied this concept for covalent RNA labeling in proof-of-principle experiments.

Chemical Proteomics Approach for Profiling the NAD Interactome

Nicotinamide adenine dinucleotide (NAD+) is a multifunctional molecule. Beyond redox metabolism, NAD+ has an equally important function as a substrate for post-translational modification enzymes, the largest family being the poly-ADP-ribose polymerases (PARPs, 17 family members in humans). The recent surprising discoveries of noncanonical NAD (NAD+/NADH)-binding proteins suggests that the NAD interactome is likely larger than previously thought; yet, broadly useful chemical tools for profiling and discovering NAD-binding proteins do not exist. Here, we describe the design, synthesis, and validation of clickable, photoaffinity labeling (PAL) probes, 2- and 6-ad-BAD, for interrogating the NAD interactome. We found that 2-ad-BAD efficiently labels PARPs in a UV-dependent manner. Chemical proteomics experiments with 2- and 6-ad-BAD identified known and unknown NAD+/NADH-binding proteins. Together, our study shows the utility of 2- and 6-ad-BAD as clickable PAL NAD probes.

Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation

1,2-Amino alcohols and α-aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. cis-Selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcohols or α-amino ketones using hydrogenation or hydrolysis, respectively.

Palladium-Catalyzed Carboxy-Alkynylation of Propargylic Amines Using Carbonate Salts as Carbon Dioxide Source

A palladium-catalyzed multicomponent reaction of propargylic amines, alkynyl bromides and cesium hydrogen carbonate to access oxazolidinones is reported. In contrast to previous reports, only a slight excess of cesium hydrogen carbonate is used as a surrogate of carbon dioxide. The reaction gives access to oxazolidinones bearing alkyl- and aryl polysubstituted enynes in good yield and very high E stereoselectivity.

Fluorescently-labeled nucleotide as well as preparation method and application thereof

The invention discloses fluorescently-labeled nucleotide. The fluorescently-labeled nucleotide has a structure represented as the formula I in the description. Stable covalent bonding is formed between dNTP (deoxyribonucleoside triphosphate) and fluorescent dye molecules represented as the formula Q, and the fluorescently-labeled nucleotide has high stability in detection environments such as serum and the like, and is high in biocompatibility and suitable for detecting nucleic acid molecules in and out of cells. Due to large Stokes shift of the fluorescent dye molecules, the fluorescently-labeled nucleotide further has the advantages of good fluorescent stability, high fluorescent quantum yield and high signal-to-noise ratio of an imaging result. The invention further discloses a preparation method of the fluorescently-labeled nucleotide. The compound with the structure shown as the formula I is prepared by a click chemical reaction, reaction conditions are mild, operation is simple,reaction selectivity is high, and the fluorescently-labeled nucleotide with high yield can be prepared.

HYDROPHILIC FLUORINATED MOLECULES FOR LIPOSOMAL 19F MRI PROBES WITH UNIQUE MR SIGNATURES

Readily available hydrophilic and small organofluorine moieties were condensed via “click chemistry” to generate nonionic hydrophilic fluorinated molecules with unique 19F MR signatures. These were used to fabricate stable liposome formulations for imaging various tissue types. This approach was tailored to exploit the broad spectrum of organic 19F molecular species and to generate probes with distinct 19F MRI signatures for simultaneous assessment of multiple molecular targets within the same target volume.

Based on molecular glue of the fluorescence-labeled nucleotide and its use in DNA sequencing

The invention discloses a fluorescence labelled nucleotide based on a molecular glue and a use thereof in DNA sequencing. The structure formula of the fluorescence labelled nucleotide is shown in a formula (I) in the specification, wherein R1 is shown in the specification, R2 is fluorescein or shown in the specification, and dNTP is ribonucleoside triphosphote which contains four different base groups; the fluorescein is selected from one of the BODIPY, rhodamine, coumarin, xanthene, cyanin, pyrene, phthalocyanine, alexa, a squarene dye, a composition for generating energy transfer dye and the derivatives thereof. The fluorescence labelled nucleotide can be used for DNA sequencing; simultaneously the raw materials for synthesizing the fluorescence labelled nucleotide are simple and easy to obtain and the fluorescence labelled nucleotide can be used for large-scale popularization. The biological assessment result shows that all the requirements of the high-throughput sequencing biochemical reaction can be satisfied by the reversible terminal, and the reversible terminal has good practical prospect.

Three nitrogen alkene company unit thereof in the synthesis of the use of DNA sequencing

The invention discloses synthesis of a triazene connection unit and an application of the triazene connection unit in DNA sequencing. The triazene connection unit has a structural formula as shown in the description, wherein -CH2OH and -CH2N3 are respecti

Synthesis of acid-sensitive connection unit and its use in DNA sequencing

The invention discloses a synthesis method of an acid sensitive connection unit, and a use of the acid sensitive connection unit in DNA sequencing. The structural formula of the acid sensitive connection unit is shown in the specification. In the structural formula, R is NH2 or N3, m is an integer from 0 to 44, and n is an integer from 0 to 44; R1 and R2 respectively represent an aliphatic alkyl group, or R1 and R2 respectively represent an aromatic derivative, or R1 is a phenyl group, a naphthyl group, a phenyl derivative or a naphthyl derivative, and R2 is an aliphatic alkyl group or hydrogen; or R2 is a phenyl group, naphthyl group, a phenyl derivative or a naphthyl derivative, R1 is an aliphatic alkyl group or hydrogen, or R1 and R2 form a cyclohexyl group, a cyclopentyl group or a cyclobutyl group. A reversible terminal obtained through connecting the acid sensitive connection unit with nucleotide and fluorescein can be used in DNA sequencing-by-synthesis. The reversible terminal can be used in the DNA sequencing; and raw materials required by the synthesis method are simple and can be easily obtained, and the synthesis process is a routine chemical reaction, so the method can realize large scale popularization use.

A rapidly photo-activatable light-up fluorescent nucleoside and its application in DNA base variation sensing

A new DNA building block (dTetU) bearing a tetrazole and allyloxy group at N-phenyl ring linked through an aminopropynyl linker to the 5-position of 2′-deoxyuridine was synthesized. The modified DNA can be lit up via a photoinduced intramolecul