6-Fluorescein phosphoramidite

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6-Fluorescein phosphoramidite

6-Fluorescein phosphoramidite | 204697-37-0

Catalog Number R10-0005
Category Fluorescein FAM
Molecular Formula C46H58N3O10P
Molecular Weight 843.94
Catalog Number Size Price Quantity
R10-0005 -- $--

Product Introduction

6-Fluorescein phosphoramidite is prepared from 6-carboxyfluorescein derivatives and does not contain 4,4'-dimethoxytrityl (DMT) groups. It can only be added once at the 5'end to terminate the synthesis.

Chemical Information

Synonyms FAM Phosphoramidite, 6-Isomer; 6-FAM phosphoramidite; FAM phosphoramidite, 6-isomer; DyLight FAM-6 CEP; 5'(6)-FAM; 5'-6-Fluorescein phosphoramidite; 6-((6-(((2-Cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)hexyl)carbamoyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate)
Purity ≥90%
IUPAC Name [6-[6-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyhexylcarbamoyl]-6'-(2,2-dimethylpropanoyloxy)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] 2,2-dimethylpropanoate
Canonical SMILES CC(C)N(C(C)C)P(OCCCCCCNC(=O)C1=CC2=C(C=C1)C(=O)OC23C4=C(C=C(C=C4)OC(=O)C(C)(C)C)OC5=C3C=CC(=C5)OC(=O)C(C)(C)C)OCCC#N
InChI InChI=1S/C46H58N3O10P/c1-29(2)49(30(3)4)60(55-25-15-22-47)54-24-14-12-11-13-23-48-40(50)31-16-19-34-37(26-31)46(59-41(34)51)35-20-17-32(56-42(52)44(5,6)7)27-38(35)58-39-28-33(18-21-36(39)46)57-43(53)45(8,9)10/h16-21,26-30H,11-15,23-25H2,1-10H3,(H,48,50)
InChI Key MGPYJVWEJNTXLC-UHFFFAOYSA-N
Solubility Soluble in Acetonitrile, DCM
Appearance White to Off-white Solid
Boiling Point 850.6±65.0°C at 760 mmHg
  • Product Specification
  • Application
ε, L⋅mol-1⋅cm-1 75000
Fluorescence Quantum Yield 0.9
Excitation 494
Emission 520
Storage Store at -20 °C

6-Fluorescein phosphoramidite, a fluorescent dye widely utilized in molecular biology and biochemical research, serves as a versatile tool in various applications. Here are four key applications:

DNA Sequencing: Deployed as a fluorescent label for nucleotides in the sequencing of DNA, 6-Fluorescein phosphoramidite sets the stage for real-time monitoring of nucleotide incorporation, thereby streamlining high-throughput sequencing processes. Its fluorescent signal enhances sequencing platform accuracy and efficiency, propelling advancements in genomics research.

Fluorescent Probes: By harnessing 6-Fluorescein phosphoramidite, researchers craft fluorescently labeled oligonucleotide probes for diverse applications, from in situ hybridization to real-time PCR. These probes, with their high sensitivity and specificity, enable the detection and quantification of specific nucleic acid sequences, essential for diagnostic assays and molecular biology studies, offering visual affirmation of target presence.

Fluorescence Resonance Energy Transfer (FRET): Engaging in FRET experiments, researchers leverage 6-Fluorescein phosphoramidite as a donor fluorophore in tandem with an appropriate acceptor fluorophore. This strategic pairing enables the scrutiny of molecular interactions and conformational alterations at the nanoscale, serving as a potent technique for unraveling protein-protein interactions, nucleic acid dynamics, and other intricate biomolecular processes.

Protein Labeling: For fluorescence-based detection and imaging studies, 6-Fluorescein phosphoramidite can be linked to proteins, allowing for the tracking of protein localization, interaction, and function within cellular and tissue contexts. This application, pivotal in cell biology and biochemistry research, furnishes insights into protein dynamics and cellular mechanisms, enriching our understanding of biological processes.

Computed Properties

XLogP3 8.5
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 12
Rotatable Bond Count 21
Exact Mass 843.38598205 g/mol
Monoisotopic Mass 843.38598205 g/mol
Topological Polar Surface Area 163Ų
Heavy Atom Count 60
Formal Charge 0
Complexity 1470
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 NumberTitlePriority Date
US-2020256857-A1 Universal histidine-tag binding compounds and methods of use thereof as fluorescent probes and sensors 2014-04-29
WO-2014120681-A2 Optical element for correcting color blindness 2013-01-29
EP-2739997-B1 Optical element for correcting color blindness 2011-08-05
US-2013032758-A1 Optical Element for Correcting Color Blindness 2011-08-05
US-2013033776-A1 Optical Element for Correcting Color Blindness 2011-08-05
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