
SIMA phosphoramidite, 6-isomer | CAS 1411797-05-1
| Catalog Number | A07-0050 |
| Category | RNA/DNA Labeling |
| Molecular Formula | C58H64N3Cl2O10P |
| Molecular Weight | 1065.02 |
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Product Introduction
SIMA (dichloro-diphenyl-fluorescein) is a xanthene dye with spectral characteristics similar to those of HEX but with a higher quantum yield. SIMA phosphoramidite is used in oligonucleotide synthesis to produce fluorescently labeled primers and hybridization probes for quantitative PCR.
Chemical Information
Product Specification
Application
Chemical Information
| Synonyms | 6-(4,7-Dichloro-2',7'-diphenyl-3',6'-dipivaloylfluorescein-6-carboxamido)-hexyl-1-O-(2-cyanoethyl)-(N,N-diisopropyl)-phosphoramidite; Propanoic acid, 2,2-dimethyl-, 1,1'-[6-[10-[bis(1-methylethyl)amino]-13-cyano-1-oxo-9,11-dioxa-2-aza-10-phosphatridec-1-yl]-4,7-dichloro-3-oxo-2',7'-diphenylspiro[isobenzofuran-1(3H),9'-[9H]xanthene]-3',6'-diyl] ester; 1,1'-[6-[10-[Bis(1-methylethyl)amino]-13-cyano-1-oxo-9,11-dioxa-2-aza-10-phosphatridec-1-yl]-4,7-dichloro-3-oxo-2',7'-diphenylspiro[isobenzofuran-1(3H),9'-[9H]xanthene]-3',6'-diyl] bis(2,2-dimethylpropanoate); SIMA; SIMA phosphoramidite, 6-isomer |
| IUPAC Name | [4,7-dichloro-6-[6-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyhexylcarbamoyl]-6'-(2,2-dimethylpropanoyloxy)-3-oxo-2',7'-diphenylspiro[2-benzofuran-1,9'-xanthene]-3'-yl] 2,2-dimethylpropanoate |
| SMILES | CC(C)N(C(C)C)P(OCCCCCCNC(=O)C1=CC(=C2C(=C1Cl)C3(C4=C(C=C(C(=C4)C5=CC=CC=C5)OC(=O)C(C)(C)C)OC6=C3C=C(C(=C6)OC(=O)C(C)(C)C)C7=CC=CC=C7)OC2=O)Cl)OCCC#N |
| InChI | InChI=1S/C58H64Cl2N3O10P/c1-35(2)63(36(3)4)74(69-29-21-26-61)68-28-20-12-11-19-27-62-52(64)41-32-44(59)49-50(51(41)60)58(73-53(49)65)42-30-39(37-22-15-13-16-23-37)45(71-54(66)56(5,6)7)33-47(42)70-48-34-46(72-55(67)57(8,9)10)40(31-43(48)58)38-24-17-14-18-25-38/h13-18,22-25,30-36H,11-12,19-21,27-29H2,1-10H3,(H,62,64) |
| InChIKey | WPCMEEMVKXSQGE-UHFFFAOYSA-N |
| Solubility | Soluble in acetonitrile and DCM |
| Appearance | White Powder |
Product Specification
| Excitation | 531 |
| Emission | 555 |
| Storage | Store at -20 °C |
Application
SIMA phosphoramidite, 6-isomer is a nucleic-acid building block designed for automated oligonucleotide synthesis, enabling the incorporation of a SIMA-derived functionality into DNA or RNA strands. This reagent format is commonly used in fluorescence labeling and nucleic-acid probe development workflows where a defined dye/handle is installed at a specific position during solid-phase synthesis, supporting downstream conjugation and imaging assay construction. Researchers typically select this phosphoramidite isomer to tune labeling placement and performance in nucleic-acid-based fluorescence experiments.
1. Oligonucleotide Fluorescent Labeling
SIMA phosphoramidite, 6-isomer is used by molecular biology and chemical biology groups to introduce a SIMA-related labeling handle directly into oligonucleotides during automated synthesis. This positional incorporation is particularly valuable when fluorescent readouts must be tied to a specific nucleotide location, such as in hybridization probes, strand displacement constructs, or labeled primers for fluorescence-based nucleic acid workflows. The resulting labeled oligonucleotides are then used in fluorescence microscopy, plate-based fluorescence assays, and other nucleic-acid imaging formats where controlled dye placement helps standardize probe behavior across batches.
2. Molecular Beacon Probe Construction
SIMA phosphoramidite, 6-isomer supports the development of fluorescence molecular beacons and related hairpin probes by allowing dye functionality to be built into the probe sequence during synthesis. In these designs, a labeled oligonucleotide can report target-dependent fluorescence changes upon hybridization, enabling real-time monitoring of nucleic acid interactions in assay development settings. Probe developers often rely on phosphoramidite incorporation to place the fluorophore/handle at a defined position relative to the stem and loop regions, improving reproducibility when screening beacon architectures for hybridization assays.
3. Fluorescent FRET Oligonucleotide Systems
SIMA phosphoramidite, 6-isomer is incorporated into donor/acceptor oligonucleotide constructs used for FRET-based nucleic acid sensing and reporting. Teams building FRET probe pairs for nucleic acid hybridization, strand displacement, or amplification-adjacent readouts benefit from the ability to install the SIMA-derived functionality at a predetermined site within the sequence. This enables systematic optimization of fluorophore spacing and labeling geometry, which is a key practical consideration when engineering FRET signal changes for fluorescence-based nucleic acid analysis platforms.
4. Labeled Primer And Probe Assay Development
SIMA phosphoramidite, 6-isomer is frequently used in assay development to generate fluorescently labeled primers and oligonucleotide probes for research-grade nucleic acid analysis workflows. In these applications, the reagent allows consistent incorporation of a SIMA-related labeling element into defined oligo reagents used for fluorescence readouts in hybridization assays, nucleic acid quantification experiments, and imaging-compatible probe panels. Oligonucleotide reagent developers value phosphoramidite-based synthesis control because it supports reproducible probe preparation for method development and comparative studies across different probe sequences.
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