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Molecules 2012, 17(10), 12378-12392; doi:10.3390/molecules171012378

Synthesis of a Cholesteryl-HEG Phosphoramidite Derivative and Its Application to Lipid-conjugates of the Anti-HIV 5'TGGGAG3' Hotoda’s Sequence

Dipartimento di Scienze Chimiche, Università di Napoli “Federico II”, Complesso Universitario di Monte Sant’Angelo, via Cintia 21, I-80126, Napoli, Italy
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Received: 19 September 2012 / Revised: 16 October 2012 / Accepted: 17 October 2012 / Published: 22 October 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
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Abstract

A novel phosphoramidite derivative of cholesterol, with an ether-linked hexaethylene glycol (HEG) spacer arm, has been obtained through simple and reproducible solid phase modified oligonucleotide synthesis manipulations. This building block and the known phosphoramidite derivative of 3b-(2-hydroxyethoxy)cholesterol have been exploited in standard oligonucleotide synthesis protocols for the preparation of 5'- conjugates of the G-quadruplex-forming 5'TGGGAG3' oligomer, known as the Hotoda’s sequence, to produce new potential anti-HIV agents.
Keywords: phosphoramidite; cholesterol; solid phase synthesis; anti-HIV G-rich oligonucleotides phosphoramidite; cholesterol; solid phase synthesis; anti-HIV G-rich oligonucleotides
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Musumeci, D.; Montesarchio, D. Synthesis of a Cholesteryl-HEG Phosphoramidite Derivative and Its Application to Lipid-conjugates of the Anti-HIV 5'TGGGAG3' Hotoda’s Sequence. Molecules 2012, 17, 12378-12392.

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