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Molecules 2010, 15(8), 5692-5707; doi:10.3390/molecules15085692

Solid-Phase Synthesis of Oligodeoxynucleotides Containing N4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine Moieties

Institute for Research in Biomedicine (IRB Barcelona), CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Institute for Advanced Chemistry of Catalonia (IQAC) CSIC, Baldiri Reixac 10, E-08028 Barcelona, Spain
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Received: 28 May 2010 / Revised: 28 July 2010 / Accepted: 5 August 2010 / Published: 18 August 2010
(This article belongs to the Special Issue Solid Phase Synthesis)
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Abstract

An efficient route for the synthesis of the phosphoramidite derivative of 5-methylcytosine bearing a tert-butylsulfanyl group protected thiol is described. This building block is used for the preparation of oligonucleotides carrying a thiol group at the nucleobase at the internal position of a DNA sequence. The resulting thiolated oligonucleotides are useful intermediates to generate oligonucleotide conjugates carrying molecules of interest at internal positions of a DNA sequence.
Keywords: solid-phase synthesis; oligonucleotides; DNA; thiol; oligonucleotide conjugates solid-phase synthesis; oligonucleotides; DNA; thiol; oligonucleotide conjugates
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Pérez-Rentero, S.; Garibotti, A.V.; Eritja, R. Solid-Phase Synthesis of Oligodeoxynucleotides Containing N4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine Moieties. Molecules 2010, 15, 5692-5707.

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