MethylPhosphonate Oligonucleotide Modification

Bio-Synthesis offers methylphosphonate (MP) DNA linkage modification. This modification introduces an electrically neutral methyl phosphonate backbone instead of the standard negative charged phosphodiester linkage. The lack of the charged group improves intracellular transport and nuclease degradation. Hence, methylphosphonate-modified DNA oligonucleotides are ideal for in vitro or in vivo antisense¹ applications where extensive exposure to nucleases is inevitable. However, methylphosphonate oligonucleotides can lower cellular uptake² of these modified oligonucleotides and their ability to hybridize to target sequences³ and also interfere with the activation of RNase H⁴.  Many antisense⁵ applications with a modified 3'- end containing a single methylphosphonate cap have successfully eliminated exonuclease degradation and prevented DNA primer extension⁶.

Methylphosphonate oligo synthesized by Bio-Synthesis can be combined with other bases and/or modified with a sugar group. These methylated oligonucleotides can be specified to be fully modified or modified with a chimeric backbone as requested by our customers. Contact us for methyphosphonate DNA or RNA synthesis.

Product Information

 

Product Name:

MethylPhosphonate Oligonucleotide Modification

Category:

Backbone Modificaiton, Neutral Charge

Modification Code:

[MPhos]

Structure:

Purification:

HPLC

Delivery Format:

Lyophilized

Shipping Conditions:

Room Temperature

Storage Conditions:

-20°C To -70°C
Oligonucleotides are stable in solution at 4°C for up to 2 weeks. Properly reconstituted material stored at -20°C should be stable for at least 6 months. Dried DNA (when kept at -20°C) in a nuclease-free environment should be stable for years.

References/Citations:

1. Sarin, P.S., Agrawal, S., Civeira, M.P., Goodchild, J., Ikeuchi, T., Zamecnik, P.C. Inhibition of acquired immunodeficiency syndrome virus by oligodeoxynucleoside methylphosphonates. Proc. Natl. Acad. Sci. USA (1988), 85: 7448-7451.
2. Blake, K.R., Murakami, A., Spitz, S.A., Glave, S.A., Reddy, M.P., Tso, P.O., Miller, P.S. Hybridization arrest of globin synthesis in rabbit reticulocyte lysates and cells by oligodeoxyribonucleoside methylphosphonates.Biochemistry (1985), 24: 6139-6145.
3. Kibler-Herzog, L., Zon, G., Uznanski, B., Whittier, G, Wilson, W.D. Duplex stabilities of phosphorothioate, methylphosphonate, and RNA analogs of two DNA 14-mers. Nucleic Acids Res. (1991), 19: 2979-2986.
4. Walder, J. Antisense DNA and RNA: progress and prospects. Genes Dev. (1988), 2: 502-504.
5. 5. Prater, C.E., Miller, P.S. 3'-Methylphosphonate-Modified Oligo-2'-O-methylribonucleotides and Their Tat Peptide Conjugates: Uptake and Stability in Mouse Fibroblasts in Culture. Bioconjugate Chem. (2004), 15: 498-507. 6. Niu, H., Xia, J., Lue, N.F. Characterization of the Interaction between the Nuclease and Reverse Transcriptase Activity of the Yeast Telomerase Complex. Mol. Cell. Biol. (2000), 20: 6806-6815.

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