Diisopropylsilyl-linked oligonucleotide analogs: solid-phase synthesis and physicochemical properties

1993 ◽  
Vol 58 (27) ◽  
pp. 7827-7831 ◽  
Author(s):  
Ashis K. Saha ◽  
Mark Sardaro ◽  
Cheryl Waychunas ◽  
Daniel Delecki ◽  
L. I. Kruse ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

scholarly journals Postsynthetic On-Column 2′ Functionalization of RNA by Convenient Versatile Method

2020 ◽  
Vol 21 (14) ◽  
pp. 5127
Author(s):  
Olga A. Krasheninina ◽  
Veniamin S. Fishman ◽  
Alexander A. Lomzov ◽  
Alexey V. Ustinov ◽  
Alya G. Venyaminova
Keyword(s):  
Chemical Synthesis ◽  
Physicochemical Properties ◽  
Functional Groups ◽  
Convenient Method ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protecting Groups ◽  
Hydroxyl Group ◽  
Phase Synthesis ◽  
Wide Range

We report a universal straightforward strategy for the chemical synthesis of modified oligoribonucleotides containing functional groups of different structures at the 2′ position of ribose. The on-column synthetic concept is based on the incorporation of two types of commercial nucleotide phosphoramidites containing orthogonal 2′-O-protecting groups, namely 2′-O-thiomorpholine-carbothioate (TC, as “permanent”) and 2′-O-tert-butyl(dimethyl)silyl (tBDMS, as “temporary”), to RNA during solid-phase synthesis. Subsequently, the support-bound RNA undergoes selective deprotection and follows postsynthetic 2′ functionalization of the naked hydroxyl group. This convenient method to tailor RNA, utilizing the advantages of solid phase approaches, gives an opportunity to introduce site-specifically a wide range of linkers and functional groups. By this strategy, a series of RNAs containing diverse 2′ functionalities were synthesized and studied with respect to their physicochemical properties.

ChemInform Abstract: Diisopropylsilyl-Linked Oligonucleotide Analogues: Solid-Phase Synthesis and Physicochemical Properties.

ChemInform ◽  
2010 ◽  
Vol 25 (20) ◽  
pp. no-no
Author(s):  
A. K. SAHA ◽  
M. SARDARO ◽  
C. WAYCHUNAS ◽  
D. DELECKI ◽  
R. KUTNY ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Oligonucleotide Analogues

Synthesis and Screening of A DNA-Encoded Library of Non-Peptidic Macrocycles

2020 ◽  
Author(s):  
Eric Koesema ◽  
Animesh Roy ◽  
Nicholas G. Paciaroni ◽  
Thomas Kodadek
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Cell Permeability ◽  
Phase Synthesis ◽  
Protein Ligands ◽  
High Affinity ◽  
Scaffold Diversity

There is considerable interest in the development of libraries of non-peptidic macrocycles as a source of ligands for difficult targets. We report here the solid-phase synthesis of a DNA-encoded library of several hundred thousand thioether-linked macrocycles. The library was designed to be highly diverse with respect to backbone scaffold diversity and to minimize the number of amide N-H bonds, which compromise cell permeability. The utility of the library as a source of protein ligands is demonstrated through the isolation of compounds that bind streptavidin, a model target, with high affinity.

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