scholarly journals Synthesis of chimera oligopeptide including furanoid β-sugar amino acid derivatives with free OHs: mild but successful removal of the 1,2-O-isopropylidene from the building block

Amino Acids ◽  
2021 ◽  
Vol 53 (2) ◽  
pp. 281-294
Author(s):  
Kim Hoang Yen Duong ◽  
Viktória Goldschmidt Gőz ◽  
István Pintér ◽  
András Perczel
Keyword(s):  
Amino Acids ◽  
Model Compound ◽  
Building Blocks ◽  
Membered Ring ◽  
Amino Acid Derivatives ◽  
Protecting Group ◽  
Sugar Amino Acids ◽  
Rp Hplc ◽  
Successful Removal ◽  
Chimeric Peptides

AbstractComplementary to hydrophobic five membered ring β-amino acids (e.g. ACPC), β-sugar amino acids (β-SAAs) have found increasing application as hydrophilic building blocks of foldamers and α/β chimeric peptides. Fmoc-protected β-SAAs [e.g. Fmoc-RibAFU(ip)-OH] are indeed useful Lego elements, ready to use for SPPS. The removal of 1,2-OH isopropylidene protecting group increasing the hydrophilicity of such SAA is presented here. We first used N3-RibAFU(ip)-OH model compound to optimize mild deprotection conditions. The formation of the 1,2-OH free product N3-RibAFU-OH and its methyl glycoside methyl ester, N3-RibAFU(Me)-OMe were monitored by RP-HPLC and found that either 50% TFA or 8 eqv. Amberlite IR-120 H+ resin in MeOH are optimal reagents for the effective deprotection. These conditions were then successfully applied for the synthesis of chimeric oligopeptide: -GG-X-GG- [X=RibAFU(ip)]. We found the established conditions to be effective and—at the same time—sufficiently mild to remove 1,2-O-isopropylidene protection and thus, it is proposed to be used in the synthesis of oligo- and polypeptides of complex sequence combination.

scholarly journals Stereoselective Access to Azetidine-Based α-Aminoacids and Applications to Small Peptides Synthesis

2020 ◽  
Author(s):  
Felix Reiners ◽  
Emanuel Joseph ◽  
Benedikt Nißl ◽  
Dorian Didier
Keyword(s):  
Amino Acids ◽  
Recent Progress ◽  
Asymmetric Reduction ◽  
Building Blocks ◽  
Membered Ring ◽  
Small Peptides ◽  
Small Peptide ◽  
Unsaturated Carboxylic Acids ◽  
Peptides Synthesis ◽  
Metal Catalyzed

Recent progress on four-membered ring building blocks has led us to investigate the formation of non-natural azetidine-based amino acids (<i>Aze</i>). A simple organometallic route was developed to access unsaturated carboxylic acids, which were further engaged in metal catalyzed asymmetric reduction. Functionalized <i>Aze</i> derivatives were finally employed in the formation of small peptide chains.

scholarly journals Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton

2009 ◽  
Vol 5 ◽  
Author(s):  
Matthias Breuning ◽  
Tobias Häuser ◽  
Christian Mehler ◽  
Christian Däschlein ◽  
Carsten Strohmann ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Side Chain ◽  
Amino Acid Derivatives ◽  
Chiral Auxiliaries ◽  
Pyrrolidine Ring ◽  
Asymmetric Organocatalysis

An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C1 or -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for β-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.

scholarly journals C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies

Amino Acids ◽  
2016 ◽  
Vol 49 (2) ◽  
pp. 223-240 ◽  
Author(s):  
Adrienn Nagy ◽  
Barbara Csordás ◽  
Virág Zsoldos-Mády ◽  
István Pintér ◽  
Viktor Farkas ◽  
...  
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Sugar Amino Acids ◽  
Coupling Strategies

scholarly journals Stereoselective Access to Azetidine-Based α-Aminoacids and Applications to Small Peptides Synthesis

2020 ◽  
Author(s):  
Felix Reiners ◽  
Emanuel Joseph ◽  
Benedikt Nißl ◽  
Dorian Didier
Keyword(s):  
Amino Acids ◽  
Recent Progress ◽  
Asymmetric Reduction ◽  
Building Blocks ◽  
Membered Ring ◽  
Small Peptides ◽  
Small Peptide ◽  
Unsaturated Carboxylic Acids ◽  
Peptides Synthesis ◽  
Metal Catalyzed

Recent progress on four-membered ring building blocks has led us to investigate the formation of non-natural azetidine-based amino acids (<i>Aze</i>). A simple organometallic route was developed to access unsaturated carboxylic acids, which were further engaged in metal catalyzed asymmetric reduction. Functionalized <i>Aze</i> derivatives were finally employed in the formation of small peptide chains.

Tropolone-Based Treatments for Visualising Latent Fingermarks on Porous Surfaces

2019 ◽  
Author(s):  
Clara M. Agapie ◽  
Melissa Sampson ◽  
William Gee
Keyword(s):  
Amino Acids ◽  
Uv Radiation ◽  
Membered Ring ◽  
Diazonium Salts ◽  
Chemical Detection ◽  
Latent Fingerprints ◽  
Porous Surfaces

The work describes a new chemical means of visualising latent fingerprints (fingermarks) using tropolone. Tropolone reacts with amino acids within the fingermark residue to form adducts that absorb UV radiation. These adducts provide useful contrast on highly-fluorescent prous surfaces will illuminated with UV radiation. The conjugated seven-membered ring of the tropolone adduct can be reacted further diazonium salts, which is demonstrated here with formation of two dyes. The methodology is extremely rapid, occurring in minutes with mild heating, and can be applied before ninhydrin in a chemical detection sequence. <br>

scholarly journals Chiroptical activity of hydroxycarboxylic acids with implications for the origin of biological homochirality

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Jana Bocková ◽  
Nykola C. Jones ◽  
Uwe J. Meierhenrich ◽  
Søren V. Hoffmann ◽  
Cornelia Meinert
Keyword(s):  
Amino Acids ◽  
Lactic Acid ◽  
Organic Molecules ◽  
Building Blocks ◽  
Aliphatic Chain ◽  
Monocarboxylic Acids ◽  
Hydroxycarboxylic Acids ◽  
Polarised Light ◽  
Suitable Target ◽  
Anisotropy Spectra

AbstractCircularly polarised light (CPL) interacting with interstellar organic molecules might have imparted chiral bias and hence preluded prebiotic evolution of biomolecular homochirality. The l-enrichment of extra-terrestrial amino acids in meteorites, as opposed to no detectable excess in monocarboxylic acids and amines, has previously been attributed to their intrinsic interaction with stellar CPL revealed by substantial differences in their chiroptical signals. Recent analyses of meteoritic hydroxycarboxylic acids (HCAs) – potential co-building blocks of ancestral proto-peptides – indicated a chiral bias toward the l-enantiomer of lactic acid. Here we report on novel anisotropy spectra of several HCAs using a synchrotron radiation electronic circular dichroism spectrophotometer to support the re-evaluation of chiral biomarkers of extra-terrestrial origin in the context of absolute photochirogenesis. We found that irradiation by CPL which would yield l-excess in amino acids would also yield l-excess in aliphatic chain HCAs, including lactic acid and mandelic acid, in the examined conditions. Only tartaric acid would show “unnatural” d-enrichment, which makes it a suitable target compound for further assessing the relevance of the CPL scenario.

scholarly journals Synthesis, Characterization and Evaluation of Peptide Nanostructures for Biomedical Applications

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4587
Author(s):  
Fanny d’Orlyé ◽  
Laura Trapiella-Alfonso ◽  
Camille Lescot ◽  
Marie Pinvidic ◽  
Bich-Thuy Doan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Biomedical Applications ◽  
Chemical Reactivity ◽  
Physical Stability ◽  
Chemical Properties ◽  
Building Blocks ◽  
Imaging Probes ◽  
Therapeutic Molecules

There is a challenging need for the development of new alternative nanostructures that can allow the coupling and/or encapsulation of therapeutic/diagnostic molecules while reducing their toxicity and improving their circulation and in-vivo targeting. Among the new materials using natural building blocks, peptides have attracted significant interest because of their simple structure, relative chemical and physical stability, diversity of sequences and forms, their easy functionalization with (bio)molecules and the possibility of synthesizing them in large quantities. A number of them have the ability to self-assemble into nanotubes, -spheres, -vesicles or -rods under mild conditions, which opens up new applications in biology and nanomedicine due to their intrinsic biocompatibility and biodegradability as well as their surface chemical reactivity via amino- and carboxyl groups. In order to obtain nanostructures suitable for biomedical applications, the structure, size, shape and surface chemistry of these nanoplatforms must be optimized. These properties depend directly on the nature and sequence of the amino acids that constitute them. It is therefore essential to control the order in which the amino acids are introduced during the synthesis of short peptide chains and to evaluate their in-vitro and in-vivo physico-chemical properties before testing them for biomedical applications. This review therefore focuses on the synthesis, functionalization and characterization of peptide sequences that can self-assemble to form nanostructures. The synthesis in batch or with new continuous flow and microflow techniques will be described and compared in terms of amino acids sequence, purification processes, functionalization or encapsulation of targeting ligands, imaging probes as well as therapeutic molecules. Their chemical and biological characterization will be presented to evaluate their purity, toxicity, biocompatibility and biodistribution, and some therapeutic properties in vitro and in vivo. Finally, their main applications in the biomedical field will be presented so as to highlight their importance and advantages over classical nanostructures.

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