solid-phase synthesis of oligodeoxynucleotides containing n4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine moieties固相合成含有陶瓷的oligodeoxynucleotides -[2 -(t-butyldisulfanyl)乙基]5-methylcytosine半个.pdf

Molecules 2010, 15, 5692-5707; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Solid-Phase Synthesis of Oligodeoxynucleotides Containing N4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine Moieties Sónia Pérez-Rentero, Alejandra V. Garibotti and Ramón Eritja * 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; E-Mails: sonia.perez@ (S.P.-R.); alejandra.garibotti@ (A.V.G.); ramon.eritja@cid.csic.es (R.E.) * Author to whom correspondence should be addressed; E-Mail: ramon.eritja@cid.csic.es; Tel.: +34-934039942; Fax: +34-932045904. Received: 28 May 2010; in revised form: 28 July 2010 / Accepted: 5 August 2010 / Published: 18 August 2010 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