
R6G phosphoramidite, 6-isomer | CAS 1355330-47-0
| Catalog Number | A19-0094 |
| Category | DNA Stains |
| Molecular Formula | C46H54F6N5O8P |
| Molecular Weight | 949.93 |
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Product Introduction
R6G phosphoramidite for oligonucleotide synthesis, pure 6-isomer.,R6G (rhodamine 6G) is a xanthene dye of the rhodamine family with high fluorescence quantum yield and high molar extinction coefficient. Relative to those of fluorescein, the absorption (518 nm) and emission (542 nm) maxima of 6-R6G are shifted into the long-wave region.,R6G can be used as a FRET acceptor in DNA-sequencing and in short tandem repeat (STR) analysis. The dye is commonly used for producing TaqMan probes for quantitative PCR. In comparison with HEX and JOE dyes, R6G in combination with BHQ1 quencher has stronger quenching in molecular beacon probes, significantly reducing background fluorescence in PCR.,Coupling: 10 minutes.,Deprotection: solution of tert-Butylamine in water (1:3 v/v) overnight at 55°С.,Aqueous ammonia and AMA (solution of 30% ammonium hydroxide/40% aqueous methylamine 1:1 v/v) must NOT be used for deprotection of the modified oligonucleotide from the solid-phase support because of complete and irreversible R6G degradation.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | N-[6-[[(2-Cyanoethoxy)](diisopropylamino)phosphinooxy]hexyl]-3-oxo-3',6'-bis[ethyl(trifluoroacetyl)amino]-2',7'-dimethylspiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carboxamide |
| Purity | NMR 1H and 31P, HPLC-MS (95+%), isomeric purity > 97% |
| IUPAC Name | N-[6-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyhexyl]-3',6'-bis[ethyl-(2,2,2-trifluoroacetyl)amino]-2',7'-dimethyl-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxamide |
| SMILES | CCN(C1=CC2=C(C=C1C)C3(C4=C(O2)C=C(C(=C4)C)N(CC)C(=O)C(F)(F)F)C5=C(C=CC(=C5)C(=O)NCCCCCCOP(N(C(C)C)C(C)C)OCCC#N)C(=O)O3)C(=O)C(F)(F)F |
| InChI | InChI=1S/C46H54F6N5O8P/c1-9-55(42(60)45(47,48)49)36-25-38-34(22-29(36)7)44(35-23-30(8)37(26-39(35)64-38)56(10-2)43(61)46(50,51)52)33-24-31(16-17-32(33)41(59)65-44)40(58)54-19-13-11-12-14-20-62-66(63-21-15-18-53)57(27(3)4)28(5)6/h16-17,22-28H,9-15,19-21H2,1-8H3,(H,54,58) |
| InChIKey | RKEJFZFXKNKKCI-UHFFFAOYSA-N |
| Solubility | Good in DCM, acetonitrile |
| Appearance | Yellowish foam |
Product Specification
| CF260 | 0.18 |
| CF280 | 0.17 |
| Fluorescence Quantum Yield | 0.95 |
| Excitation | 518 |
| Emission | 542 |
| Storage | Storage: 12 months after receival at -20 °C in the Dark. Transportation: at room temperature for up to 2 weeks. Avoid prolonged exposure to light. Desiccate. |
Application
R6G phosphoramidite, 6-isomer is a rhodamine 6G-derived fluorescent building block provided in a phosphoramidite format, enabling efficient incorporation into oligonucleotides for fluorescent labeling and probe construction. Its rhodamine fluorophore core supports bright visible fluorescence for fluorescence imaging and assay development, while the phosphoramidite handle is designed for nucleic acid conjugation workflows. Researchers use this reagent to generate defined, site-specific fluorescent oligo conjugates for microscopy and fluorescence-based analytical assays.
1. Oligonucleotide Fluorescent Labeling
R6G phosphoramidite, 6-isomer is used by molecular biology and chemical biology teams to install a rhodamine 6G fluorophore at a defined position within DNA or RNA during oligonucleotide synthesis. This enables construction of fluorescently tagged primers, probes, and standards used in nucleic acid workflows where controlled dye placement and consistent conjugate structure are important. Common downstream uses include fluorescence-based readouts for nucleic acid binding studies, hybridization experiments, and labeled oligo controls for assay optimization.
2. Fluorescence Microscopy Tracing
R6G phosphoramidite, 6-isomer supports cellular and molecular imaging workflows that rely on fluorescent nucleic acid tracers. By producing fluorescent oligonucleotides with a rhodamine 6G signal, researchers can visualize labeled nucleic acid behavior in microscopy experiments such as uptake/trafficking studies, localization tracking of nucleic acid probes, and fluorescence-guided sample characterization. The phosphoramidite format is particularly valuable when a defined dye position on the oligo is required for reproducible imaging performance across experimental batches.
3. FRET Probe Oligos
R6G phosphoramidite, 6-isomer is frequently incorporated into oligonucleotide-based FRET systems where rhodamine emission serves as a donor or acceptor component within a nucleic acid context. Teams developing fluorescence resonance energy transfer probes use dye-labeled oligos to monitor hybridization-dependent proximity changes, conformational shifts, or target-driven assembly of fluorescent components. This reagent is especially useful for building FRET probe architectures that require precise fluorophore installation on the same synthetic platform as the recognition sequence.
4. Fluorescent Nucleic Acid Standards
R6G phosphoramidite, 6-isomer is also used to prepare fluorescent oligonucleotide standards and calibration reagents for fluorescence quantification in nucleic acid analysis. Researchers employ dye-labeled oligos as reference materials for instrument setup, assay normalization, and method development in fluorescence-based nucleic acid assays. Because the dye is introduced through the oligo synthesis workflow, the resulting conjugates provide a consistent fluorescent reporter for comparing signal across experiments and batches.
Computed Properties
| XLogP3 | 8.6 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 19 |
| Exact Mass | 949.36141967 g/mol |
| Monoisotopic Mass | 949.36141967 g/mol |
| Topological Polar Surface Area | 151Ų |
| Heavy Atom Count | 66 |
| Formal Charge | 0 |
| Complexity | 1660 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2012016128-A1 | Rhodamine lactone phosphoramidites and polymers | 2010-07-16 |
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