synthesis of oligonucleotides carrying thiol groups using a simple reagent derived from threoninol合成寡核苷酸携带巯基共同使用一个简单的试剂来自threoninol.pdf

Molecules 2012, 17, 10026-10045; doi:10.3390/molecules170910026 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of Oligonucleotides Carrying Thiol Groups Using a Simple Reagent Derived from Threoninol Sonia Pérez-Rentero 1,2, Santiago Grijalvo 1,2, Rubén Ferreira 1,2 and Ramon Eritja 1,2,* 1 Institute for Research in Biomedicine (IRB Barcelona), Baldiri Reixac 10, E-08028 Barcelona, Spain; E-Mails: sonia.perez@ (S.P.-R.); santiago.grijalvo@ (S.G.); ruben.ferreira@ (R.F.) 2 Institute for Advanced Chemistry of Catalonia (IQAC), CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Jordi Girona 18, E-08034 Barcelona, Spain * Author to whom correspondence should be addressed; E-Mails: recgma@cid.csic.es or ramon.eritja@; Tel.: +34-93-403-9942; Fax: +34-93-204-5904. Received: 27 June 2012; in revised form: 3 August 2012 / Accepted: 14 August 2012 / Published: 24 August 2012 Abstract: Oligonucleotides carrying thiol groups are useful intermediates for a remarkable number of applications involving nucleic acids. In this study, DNA oligonucleotides carrying tert-butylsulfanyl (t-BuS) protected thiol groups have been prepared. A building block derived from threoninol has been developed to introduce a thiol group at any predetemined position of an oligonucleotide. The resulting thiolated oligonucleotides have been used for the preparation of oligonucleotide conjugates and for the functionalization of gold nanoparticles using the reactivity of the