scholarly journals DNA functionalization by dynamic chemistry

2016 ◽  
Vol 12 ◽  
pp. 2136-2144 ◽  
Author(s):  
Zeynep Kanlidere ◽  
Oleg Jochim ◽  
Marta Cal ◽  
Ulf Diederichsen
Keyword(s):  
Deoxyribonucleic Acid ◽  
Solid Phase ◽  
Building Blocks ◽  
Thermodynamic Control ◽  
Dna Templates ◽  
Phase Synthesis ◽  
Dynamic Combinatorial Chemistry ◽  
Dna Oligonucleotides ◽  
Reversible Reactions ◽  
Modified Nucleobases

Dynamic combinatorial chemistry (DCC) is an attractive method to efficiently generate libraries of molecules from simpler building blocks by reversible reactions under thermodynamic control. Here we focus on the chemical modification of DNA oligonucleotides with acyclic diol linkers and demonstrate their potential for the deoxyribonucleic acid functionalization and generation of libraries of reversibly interconverting building blocks. The syntheses of phosphoramidite building blocks derived from D-threoninol are presented in two variants with protected amino or thiol groups. The threoninol building blocks were successfully incorporated via automated solid-phase synthesis into 13mer oligonucleotides. The amino group containing phosphoramidite was used together with complementary single-strand DNA templates that influenced the Watson–Crick base-pairing equilibrium in the mixture with a set of aldehyde modified nucleobases. A significant fraction of all possible base-pair mismatches was obtained, whereas, the highest selectivity (over 80%) was found for the guanine aldehyde templated by the complementary cytosine containing DNA. The elevated occurrence of mismatches can be explained by increased backbone plasticity derived from the linear threoninol building block as a cyclic deoxyribose analogue.

Development of Strategies for Glycopeptide Synthesis: An Overview on the Glycosidic Linkage

2020 ◽  
Vol 24 (21) ◽  
pp. 2475-2497
Author(s):  
Andrea Verónica Rodríguez-Mayor ◽  
German Jesid Peralta-Camacho ◽  
Karen Johanna Cárdenas-Martínez ◽  
Javier Eduardo García-Castañeda
Keyword(s):  
Chemical Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Heterogeneous Environments ◽  
Phase Synthesis ◽  
Low Concentrations ◽  
Biological Sources ◽  
Synthetic Routes ◽  
The Impact ◽  
Potential Use

Glycoproteins and glycopeptides are an interesting focus of research, because of their potential use as therapeutic agents, since they are related to carbohydrate-carbohydrate, carbohydrate-protein, and carbohydrate-lipid interactions, which are commonly involved in biological processes. It has been established that natural glycoconjugates could be an important source of templates for the design and development of molecules with therapeutic applications. However, isolating large quantities of glycoconjugates from biological sources with the required purity is extremely complex, because these molecules are found in heterogeneous environments and in very low concentrations. As an alternative to solving this problem, the chemical synthesis of glycoconjugates has been developed. In this context, several methods for the synthesis of glycopeptides in solution and/or solid-phase have been reported. In most of these methods, glycosylated amino acid derivatives are used as building blocks for both solution and solid-phase synthesis. The synthetic viability of glycoconjugates is a critical parameter for allowing their use as drugs to mitigate the impact of microbial resistance and/or cancer. However, the chemical synthesis of glycoconjugates is a challenge, because these molecules possess multiple reaction sites and have a very specific stereochemistry. Therefore, it is necessary to design and implement synthetic routes, which may involve various protection schemes but can be stereoselective, environmentally friendly, and high-yielding. This review focuses on glycopeptide synthesis by recapitulating the progress made over the last 15 years.

scholarly journals Recovery, Purification, and Reusability of Building Blocks for Solid Phase Synthesis

2019 ◽  
Vol 41 (2) ◽  
pp. 1900473
Author(s):  
Fadi Shamout ◽  
Lukas Fischer ◽  
Nicole L. Snyder ◽  
Laura Hartmann
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis

Concise solid-phase synthesis of inverse poly(amidoamine) dendrons using AB2 building blocks

2013 ◽  
Vol 49 (51) ◽  
pp. 5784 ◽  
Author(s):  
Adela Ya-Ting Huang ◽  
Ching-Hua Tsai ◽  
Hsing-Yin Chen ◽  
Hui-Ting Chen ◽  
Chi-Yu Lu ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis

Cyclic Enzymatic Solid Phase Synthesis of Isotopically Labeled DNA Oligonucleotides

2009 ◽  
Vol 28 (11-12) ◽  
pp. 1030-1041 ◽  
Author(s):  
Ahmed M. Khan ◽  
Subrata H. Mishra ◽  
Markus W. Germann
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Dna Oligonucleotides

scholarly journals Modular automated solid phase synthesis of dermatan sulfate oligosaccharides

2014 ◽  
Vol 50 (15) ◽  
pp. 1875-1877 ◽  
Author(s):  
Jeyakumar Kandasamy ◽  
Frank Schuhmacher ◽  
Heung Sik Hahm ◽  
James C. Klein ◽  
Peter H. Seeberger
Keyword(s):  
Solid Phase Synthesis ◽  
Dermatan Sulfate ◽  
Solid Phase ◽  
Building Blocks ◽  
Automated Synthesis ◽  
Phase Synthesis ◽  
Iduronic Acid

Orthogonally protected d-galactosamine and l-iduronic acid building blocks and a photo-cleavable linker are instrumental for the automated synthesis of dermatan sulfate oligosaccharides.

Sign in / Sign up

Export Citation Format

Share Document