PDNA as building blocks for membrane-guided self-assemblies

Different semi-synthetic PDNAs (protein–DNA complexes), which encompass a protein core engineered from the cytochrome b5 scaffold, an embedded tuneable redox cofactor, a synthetic linker and a large oligonucleotide, were designed, synthesized and purified to homogeneity. These building blocks can be reversibly attached to Ni-DOGS {1,2-dioleoyl-sn-glycero-3-[N(5-amino-1-carboxypentyl)iminodiacetic acid]succinyl}-doped supported membranes through a metal chelate bridge with the protein part and be polymerized in a fully controllable manner using a solid-phase synthesis strategy and a stepwise addition of suitable complementary oligonucleotides. The resulting structures could recreate a large range of regular distribution of patterned redox and absorbing centres separated by fully tuneable distances and geometry. Kinetic parameters for the self-assembly of building blocks were determined using SPRI (surface plasmon resonance imagery). Structures of resulting nano-objects were characterized using gel electrophoresis and single molecule approaches following decoration of assemblies with quantum dots.

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A convenient solid-phase synthesis methodology for preparing peptide-derived molecular imaging agents Synthesis, characterization, and in vitro screening of Tc(I) chemotactic peptide conjugates

Canadian Journal of Chemistry ◽

10.1139/v05-224 ◽

2005 ◽

Vol 83 (12) ◽

pp. 2060-2066 ◽

Cited By ~ 10

Author(s):

Karin A Stephenson ◽

Sangeeta Ray Banerjee ◽

Nicole McFarlane ◽

Douglas R Boreham ◽

Kevin P Maresca ◽

...

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Metal Chelate ◽

Free Ligand ◽

Peptide Sequence ◽

In Vitro Screening ◽

Chemotactic Peptide ◽

Phase Synthesis ◽

Synthesis Strategy

A versatile solid-phase synthesis strategy for preparing peptidechelate conjugates was developed. The methodology was optimized using a series of ligands, designed to bind Tc(I)/Re(I), and a chemotactic peptide fMFL, which was exploited as a model targeting vector. The peptide derivatives were prepared in parallel using a conventional automated peptide synthesizer in multi-milligram quantities, which provided sufficient material to perform complete characterization, radiolabelling, and in vitro screening studies. Because of the robust nature of the metalchelate complexes, the Re complex of a chelatepeptide conjugate was prepared on the resin using the same methodology employed to prepare the free ligand conjugates. As such, the reported methodology is amenable to the preparation of libraries of novel Tc radiopharmaceutical ligands and their corresponding Re reference standards in which several factors, including peptide sequence, site of derivatization, and both the type and length of the spacer, can be easily varied.Key words: radiopharmaceuticals, technetium, rhenium, peptides, solid-phase synthesis.

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

Current Organic Chemistry ◽

10.2174/1385272824999200701121037 ◽

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.

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Synthesis and Self-assembly of Amphiphilic Precision Glycomacromolecules

Polymer Chemistry ◽

10.1039/d1py00422k ◽

2021 ◽

Author(s):

Alexander Banger ◽

Julian Sindram ◽

Marius Otten ◽

Jessica Kania ◽

Alexander Strzelczyk ◽

...

Keyword(s):

Self Assembly ◽

Solid Phase ◽

Building Blocks ◽

Polymer Synthesis

We present the synthesis of so called amphiphilic glycomacromolecules (APGs) by using solid-phase polymer synthesis. Based on tailor made building blocks, monosdisperse APGs with varying compositions are synthesized, introducing carbohydrate...

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