6-TAMRA phosphoramidite

Oligonucleotides modified with TAMRA derivatives can be used for genomic research, molecular diagnosis, and molecular biology.

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Catalog

BRP-02239

Synonyms

TAMRA phosphoramidite, 6-isomer; N-(6-oxo-6-[(3R,5S)-5-[(4,4'-dimethoxytrityl)-oxymethyl]-3-(N,N-diisopropylamino-2-cyanoethoxyphosphin-oxy)pyrrolidine-1-yl]hexyl)-3',6'-Bis(dimethylamino)-3-oxo-spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-yl-carboxamide

IUPAC Name

(3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-1-(6-(3',6'-bis(dimethylamino)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-6-carboxamido)hexanoyl)pyrrolidin-3-yl (2-cyanoethyl) diisopropylphosphoramidite

Molecular Weight

1145.35

Molecular Formula

C66H77N6O10P

InChI

InChI=1S/C66H77N6O10P/c1-44(2)72(45(3)4)83(79-37-17-35-67)82-55-39-52(43-78-65(47-18-13-11-14-19-47,48-22-28-53(76-9)29-23-48)49-24-30-54(77-10)31-25-49)71(42-55)62(73)20-15-12-16-36-68-63(74)46-21-32-56-59(38-46)66(81-64(56)75)57-33-26-50(69(5)6)40-60(57)80-61-41-51(70(7)8)27-34-58(61)66/h11,13-14,18-19,21-34,38,40-41,44-45,52,55H,12,15-17,20,36-37,39,42-43H2,1-10H3,(H,68,74)/t52-,55+,83?/m0/s1

InChIKey

VDRDQKBQFCBCQK-FYICZBFESA-N

Purity

>95%

Solubility

Soluble in acetonitrile, DCM

Appearance

Dark red solid

Storage

Store at -20 °C

Symbol

5'-TAMRA phosphoramidite (6-TAMRA)

Chemical Structure:

Reference Reading

1. Practical synthesis of isomerically pure 5- and 6-carboxytetramethylrhodamines, useful dyes for DNA probes

Maksim V Kvach, Irina A Stepanova, Igor A Prokhorenko, Aleksander P Stupak, Dmitry A Bolibrukh, Vladimir A Korshun, Vadim V Shmanai. Bioconjug Chem. 2009 Aug 19;20(8):1673-82. doi: 10.1021/bc900037b.

Simple and scalable synthesis of 5- and 6-carboxytetramethylrhodamines (TAMRAs) is reported. Acylation of 3-dimethylaminophenol with 1,2,4-benzenetricarboxylic anhydride afforded a mixture of 4-dimethylamino-2-hydroxy-2',4'(5')-dicarboxybenzophenones, which can be easily separated into individual compounds upon recrystallization from methanol and acetic acid. Individual benzophenones were reacted with 3-dimethylaminophenol to give 5- or 6-carboxytetramethylrhodamines. The dyes were converted into hydroxyprolinol-based phosphoramidite reagents suitable for oligonucleotide synthesis. 5- and 6-TAMRA isomers on oligonucleotides showed similar absorption and emission spectra. Fluorescence quantum yield of the dyes correlates with the presence of dG nucleosides in the adjacent region of oligonucleotide sequence. Several energy transfer primers containing on their 5'-termini (6-FAM)dT(n)(6-TAMRA) dye system (n = 0, 2, 4, 6, 8, 10, 12, 14) were prepared, and their spectral properties were studied.