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H-Phosphonate dA. dA(H-p)

picture of H-Phosphonate dA. dA(H-p)

Modification : H-Phosphonate dA. dA(H-p)

Catalog Reference Number
Category
Modification Code
5 Prime
3 Prime
Internal
Molecular Weight (mw)
Extinction Coeficient (ec)
Technical Info (pdf)
Absorbance MAX
Emission MAX
Absorbance EC



26-6581
Others
H-p dA
Y
Y
Y
298.2
15.4
PS26-6581.pdf
-
-
-


Catalog NoScalePrice
26-6581-0550 nmol$60.00
26-6581-02200 nmol$60.00
26-6581-011 umol$78.00
26-6581-032 umol$117.00
26-6581-1010 umol$624.00
26-6581-1515 umol$780.00

H-phosphonoamidites are deoxynucleoside amidites modified such that, when incorporated into an oligonucleotide, that base position will have an H-phosphonate backbone linkage instead of the standard phosphodiester linkage. In the H-phosphonate linkage, one of the oxygen bound to the phosphorus atom in a phosphodiester linkage has been replaced by hydrogen. H-phosphonate-modified oligos are typically synthesized when a researcher wants to prepare a S-35 radiolabeled phosphorothioate linkage (1). For the radiolabeled phosphorothioate, an H-phosphonate linkage is incorporated at the desired position using phosphoramidite chemistry, and then S-35 is used to replace the hydrogen atom via a sulfurization reaction (2). For the phosphoroamidate, N,N-dimethylaminoethylamine is reacted with the H-phosphonate to form the substituted linkage. Phosphoroamidates, being a cationic linkage, may provide nuclease resistance and improved cell permeability (3).

References
1. Maier, M.A., Guzaev, A.P., Manoharan, M. Synthesis of Chimeric Oligonucleotides Containing Phosphodiester, Phosphorothioate, and Phosphoramidate Linkages. Org. Lett. (2000), 2: 1819-1822.
2. Wallin, R., Kalek, M., Bartoszewicz, A., Thelin, M., Stawinski, J. On the Sulfurization of H-Phosphonate Diesters and Phosphite Triesters Using Elemental Sulfur.Phosphorus, Sulfur, and Silicon (2009), 184: 908-916.
3. Letsinger, R.L., Singman, C.N., Histand, G., Salunkhe, M. Cationic Oligonucleotides.J. Am. Chem. Soc. (1988), 1110: 4470-4471.
- H-Phosphonate dA. dA(H-p)

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