Solid-Phase Synthesis of Glyco-Oligonucleotide Conjugates

Synlett ◽  
2001 ◽  
Vol 2001 (06) ◽  
pp. 0745-0748 ◽  
Author(s):  
Matteo Adinolfi ◽  
Lorenzo De Napoli ◽  
Giovanni Di Fabio ◽  
Luigi Guariniello ◽  
Alfonso Iadonisi ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Oligonucleotide Conjugates

scholarly journals A Trisbenzimidazole Phosphoramidite Building Block Enables High-Yielding Syntheses of RNA-Cleaving Oligonucleotide Conjugates

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1842
Author(s):  
Felix Zellmann ◽  
Michael W. Göbel
Keyword(s):  
Building Block ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Reaction Rates ◽  
Phase Synthesis ◽  
Active Ester ◽  
Specific Manner ◽  
The Impact ◽  
Oligonucleotide Conjugates

The RNA cleaving catalyst tris(2-aminobenzimidazole) when attached to the 5’ terminus of oligonucleotides cuts complementary RNA strands in a highly site-specific manner. Conjugation was previously achieved by the acylation of an amino linker by an active ester of the catalyst. However, this procedure was low yielding and not reliable. Here, a phosphoramidite building block is described that can be coupled to oligonucleotides by manual solid phase synthesis in total yields around 85%. Based on this chemistry, we have now studied the impact of LNA (locked nucleic acids) nucleotides on the rates and the site-specificities of RNA cleaving conjugates. The highest reaction rates and the most precise cuts can be expected when the catalyst is attached to a strong 5’ closing base pair and when the oligonucleotide contains several LNA units that are equally distributed in the strand. However, when placed in the 5’ position, LNA building blocks tend to diminish the specificity of RNA cleavage.

Towards a general method for the stepwise solid-phase synthesis of peptide–oligonucleotide conjugates

2002 ◽  
Vol 43 (3) ◽  
pp. 527-530 ◽  
Author(s):  
Maxim Antopolsky ◽  
Elena Azhayeva ◽  
Unni Tengvall ◽  
Alex Azhayev
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Oligonucleotide Conjugates ◽  
General Method

Glycomimetics as Decorating Motifs for Oligonucleotides:  Solid-Phase Synthesis, Stability, and Hybridization Properties of Carbopeptoid−Oligonucleotide Conjugates

2005 ◽  
Vol 16 (5) ◽  
pp. 1299-1309 ◽  
Author(s):  
Jennifer D'Onofrio ◽  
Marcella de Champdoré, ◽  
Lorenzo De Napoli ◽  
Daniela Montesarchio ◽  
Giovanni Di Fabio
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Oligonucleotide Conjugates

scholarly journals Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4266 ◽  
Author(s):  
Mariya I. Meschaninova ◽  
Darya S. Novopashina ◽  
Olga A. Semikolenova ◽  
Vladimir N. Silnikov ◽  
Alya G. Venyaminova
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Polymer Support ◽  
Phase Synthesis ◽  
Wide Range ◽  
Different Types ◽  
Convenient Approach ◽  
Aliphatic Diamines ◽  
Oligonucleotide Conjugates ◽  
Derivatives Of

A novel and convenient approach for the solid-phase 5′-functionalization of oligonucleotides is proposed in this article. The approach is based on the activation of free 5′-hydroxyl of polymer support-bound protected oligonucleotides by N,N′-disuccinimidyl carbonate followed by interaction with amino-containing ligands. Novel amino-containing derivatives of closo-dodecaborate, estrone, cholesterol, and α-tocopherol were specially prepared. A wide range of oligonucleotide conjugates bearing closo-dodecaborate, short peptide, pyrene, lipophilic residues (cholesterol, α-tocopherol, folate, estrone), aliphatic diamines, and propargylamine were synthesized and characterized to demonstrate the versatility of the approach. The developed method is suitable for the conjugate synthesis of oligonucleotides of different types (ribo-, deoxyribo-, 2′-O-methylribo-, and others).

Solid-Phase Synthesis of Azaphthalocyanine−Oligonucleotide Conjugates and Their Evaluation As New Dark Quenchers of Fluorescence

2010 ◽  
Vol 21 (10) ◽  
pp. 1872-1879 ◽  
Author(s):  
Kamil Kopecky ◽  
Veronika Novakova ◽  
Miroslav Miletin ◽  
Radim Kučera ◽  
Petr Zimcik
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Oligonucleotide Conjugates
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