Fluorinated aminoanthranilamides: non-native amino acids for bringing proteomic approaches to charge-transfer systems

2017 ◽  
Vol 19 (11) ◽  
pp. 7871-7876 ◽  
Author(s):  
Jillian M. Larsen-Clinton ◽  
Eli M. Espinoza ◽  
Maximillian F. Mayther ◽  
John Clark ◽  
Christina Tao ◽  
...  
Keyword(s):  
Amino Acids ◽  
Charge Transfer ◽  
Building Blocks ◽  
Selective Substitution

A highly selective substitution leads to a set of unique non-native amino acids that can serve as building blocks for molecular electrets.

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.

Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Amino Alcohols

1996 ◽  
Vol 61 (2) ◽  
pp. 288-297 ◽  
Author(s):  
Vladimír Pouzar ◽  
Ivan Černý
Keyword(s):  
Amino Acids ◽  
Hydroxy Group ◽  
Building Blocks ◽  
Amino Alcohols ◽  
New Approach ◽  
Alternative Synthesis ◽  
Oxime Derivatives ◽  
A Chain ◽  
Derivatives Of

New approach to the preparation of steroids with connecting bridge, based on an O-carboxymethyloxime (CMO) structure, and with terminal hydroxy group, is presented. 17-CMO derivatives of 3β-acetoxy- and 3β-methoxymethoxyandrost-5-en-17-one were condensed with α,ω-amino alcohols to give derivatives with a chain of seven to nine atoms. After THP-protection, these compounds were converted to 3-keto-4-ene derivatives. An alternative synthesis consisted in transformation of 17-CMO derivatives with bonded amino acids by reduction of the terminal carboxyl. The resulting compounds were designed as building blocks for the preparation of bis-haptens for sandwich immunoassays.

scholarly journals An aza-Diels–Alder route to quinoline-based unnatural amino acids and polypeptide surrogates

RSC Advances ◽  
2021 ◽  
Vol 11 (23) ◽  
pp. 14132-14139
Author(s):  
M. J. Umerani ◽  
H. Yang ◽  
P. Pratakshya ◽  
J. S. Nowick ◽  
A. A. Gorodetsky
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Building Blocks ◽  
Solid Support ◽  
Diels Alder

The synthesis of quinoline-based unnatural amino acids and the subsequent preparation of polypeptide surrogates from these building blocks on solid support.

Amino Acids Profiling in Fruit Juices by High Performance Liquid Chromatography: A Review

2020 ◽  
Vol 11 (SPL4) ◽  
pp. 2756-2767
Author(s):  
Vijaya Vemani ◽  
Mounika P ◽  
Poulami Das ◽  
Anand Kumar Tengli
Keyword(s):  
Amino Acids ◽  
High Performance Liquid Chromatography ◽  
Liquid Chromatography ◽  
High Performance ◽  
Amino Acid Content ◽  
Building Blocks ◽  
Fruit Juices ◽  
The Body ◽  
Total Amino Acid ◽  
Analytical Approaches

In the preservation of normal physiological functions, the building blocks of the body called amino acids play a crucial role. A number of valuable and nutritional phytoconstituents are contained in fruit juices, such as vitamins, minerals, microelements, organic acids, antioxidants, flavonoids, amino acids and other components. Due to the growing population and demand, the quality of fruit juices is decreasing. One of the unethical and harmful practices called adulteration or food fraudulence has been adopted by most food and beverage industries. The amino acids which is one of the most important phytochemicals of fruit and fruit juices which affects the organoleptic properties like color, odor, and taste of juices and also helps in authenticity process from governing bodies by providing total amino acid content. Consequently, the main aim of the present review work is to provide information regarding the importance of amino acids, how they are adulterated, the potential analytical approach to detected amino acids and which methods are generally accepted method by the food industries. According to the literature review, we presume that reverse phased high-performance liquid chromatography with pre-column derivatization was the most adopted method for quality checking due to its advantages over other old and recent analytical approaches like simple, rapid, cost-effective nature, less / no sample matrix effect with high sensitivity, accuracy, and precision.

scholarly journals Synthesis of new Cα-tetrasubstituted α-amino acids

2009 ◽  
Vol 5 ◽  
Author(s):  
Andreas A Grauer ◽  
Burkhard König
Keyword(s):  
Amino Acids ◽  
Secondary Structure ◽  
Aromatic Aldehydes ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Peptide Backbone ◽  
Aliphatic Aldehydes ◽  
New Class ◽  
Cyclic Amino Acids

Cα-Tetrasubstituted α-amino acids are important building blocks for the synthesis of peptidemimetics with stabilized secondary structure, because of their ability to rigidify the peptide backbone. Recently our group reported a new class of cyclic Cα-tetrasubstituted tetrahydrofuran α-amino acids prepared from methionine and aromatic aldehydes. We now report the extension of this methodology to aliphatic aldehydes. Although such aldehydes are prone to give aldol products under the reaction conditions used, we were able to obtain the target cyclic amino acids in low to moderate yields and in some cases with good diastereoselectivity.

scholarly journals Stereocontrolled Synthesis of Cyclopropanol Amino Acids from Allylic Sulfones: Conformationally Restricted Building Blocks.

ChemInform ◽  
2004 ◽  
Vol 35 (5) ◽  
Author(s):  
David Diez ◽  
P. Garcia ◽  
Isidro S. Marcos ◽  
N. M. Garrido ◽  
P. Basabe ◽  
...  
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Conformationally Restricted ◽  
Stereocontrolled Synthesis

ChemInform Abstract: Blue Fluorescent Amino Acids as in vivo Building Blocks for Proteins

ChemInform ◽  
2010 ◽  
Vol 41 (17) ◽  
Author(s):  
Lars Merkel ◽  
Michael G. Hoesl ◽  
Marcel Albrecht ◽  
Andreas Schmidt ◽  
Nediljko Budisa
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Fluorescent Amino Acids

scholarly journals A Straightforward Methodology to Overcome Solubility Challenges for N-Terminal Cysteinyl Peptide Segments Used in Native Chemical Ligation

2020 ◽  
Author(s):  
Skander Abboud ◽  
El hadji Cisse ◽  
Michel Doudeau ◽  
Hélène Bénédetti ◽  
Vincent AUCAGNE
Keyword(s):  
Amino Acids ◽  
Chemical Synthesis ◽  
Building Blocks ◽  
Native Chemical Ligation ◽  
Synthetic Approach ◽  
Chemical Ligation ◽  
Limited Solubility ◽  
Peptide Segments

One of the main limitations encountered during the chemical synthesis of proteins through native chemical ligation (NCL) is the limited solubility of some of the peptide segments. The most commonly used solution to overcome this problem is to derivatize the segment with a temporary solubilizing tag. Conveniently, the tag can be introduced on the thioester segment in such a way that it is removed concomitantly with the NCL reaction. We herein describe a generalization of this approach to N-terminal cysteinyl segment counterparts, using a straightforward synthetic approach that can be easily automated from commercially available building blocks, and applied it to a well-known problematic target, SUMO-2 (93 amino acids).

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