scholarly journals Heteroaromatic N-Oxides Modified with a Chiral Oxazoline Moiety, Synthesis and Catalytic Applications

Catalysts ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 444
Author(s):  
Zuzanna Wrzeszcz ◽  
Renata Siedlecka
Keyword(s):  
Amino Acids ◽  
Amino Alcohols ◽  
Starting Point ◽  
Nitroaldol Reaction ◽  
Catalytic Applications ◽  
The Stability ◽  
Natural Amino Acids

Interesting properties of N-oxides and pyridine oxazoline compounds have become the starting point to synthesize compounds connecting both groups. A multi-step synthesis of a series of chiral oxazoline substituted pyridine N-oxides, alkyl derived of pyridine N-oxides, bipyridine N-oxides, and isoquinoline N-oxides, based on amino alcohols derived from natural amino acids or other previously prepared, is presented herein. Various synthetic pathways have been designed and tested according to the properties and limitations imposed by the target products. The encountered problems related to the stability of the products were discussed. The resulting compounds (eighteen structures) were tested as catalysts in th e allylation of benzaldehyde (obtaining up to 79% ee) as well as in nitroaldol reaction (obtaining up to 48% ee).

scholarly journals Impact of non-proteinogenic amino acids in the discovery and development of peptide therapeutics

Amino Acids ◽  
2020 ◽  
Vol 52 (9) ◽  
pp. 1207-1226
Author(s):  
Yun Ding ◽  
Joey Paolo Ting ◽  
Jinsha Liu ◽  
Shams Al-Azzam ◽  
Priyanka Pandya ◽  
...  
Keyword(s):  
Amino Acids ◽  
Its Sequence ◽  
Peptide Therapeutics ◽  
Large Proteins ◽  
Drug Candidates ◽  
Ongoing Development ◽  
The Stability ◽  
Natural Amino Acids ◽  
The Impact ◽  
As Toxicity

Abstract With the development of modern chemistry and biology, non-proteinogenic amino acids (NPAAs) have become a powerful tool for developing peptide-based drug candidates. Drug-like properties of peptidic medicines, due to the smaller size and simpler structure compared to large proteins, can be changed fundamentally by introducing NPAAs in its sequence. While peptides composed of natural amino acids can be used as drug candidates, the majority have shown to be less stable in biological conditions. The impact of NPAA incorporation can be extremely beneficial in improving the stability, potency, permeability, and bioavailability of peptide-based therapies. Conversely, undesired effects such as toxicity or immunogenicity should also be considered. The impact of NPAAs in the development of peptide-based therapeutics is reviewed in this article. Further, numerous examples of peptides containing NPAAs are presented to highlight the ongoing development in peptide-based therapeutics.

Chiral amino alcohols derived from natural amino acids as chiral solvating agents for carboxylic acids

2008 ◽  
Vol 19 (10) ◽  
pp. 1193-1199 ◽  
Author(s):  
Wenge Wang ◽  
Xiumin Shen ◽  
Fengnian Ma ◽  
Zijing Li ◽  
Cong Zhang
Keyword(s):  
Amino Acids ◽  
Carboxylic Acids ◽  
Amino Alcohols ◽  
Natural Amino Acids ◽  
Chiral Amino Alcohols

Synthesis and characteristics of ethylenediamine-N,N'-di-S-α-isovalerate and isomers of its cobalt(III) complexes

1982 ◽  
Vol 47 (1) ◽  
pp. 210-216 ◽  
Author(s):  
Milan Strašák ◽  
František Bachratý ◽  
Jaroslav Majer
Keyword(s):  
Amino Acids ◽  
Absolute Configuration ◽  
Electronic Absorption ◽  
Electronic Absorption Spectra ◽  
Chemical Parameters ◽  
Methyl Group ◽  
Nmr Data ◽  
Physico Chemical ◽  
Natural Amino Acids ◽  
C Nmr

The synthesis and physico-chemical parameters are described of a new complexone based on natural amino acids, viz. ethylenediamine-N,N'-di-S-α-isovalerate (SS-EDDIV). 1H- and 13C-NMR data revealed that the methyl group in the substance are not equivalent. The isomers of the cobalt(III) complex with the asymmetric tetradentate SS-EDDIV ligand were prepared and separated; their characteristics are given. The absolute configuration of two of the five theoretically feasible isomers was determined based on their electronic absorption spectra and circular dichroism data.

scholarly journals Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids, Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes

2021 ◽  
Author(s):  
Eryn Nelson ◽  
Jeffrey S. S. K. Formen ◽  
Christian Wolf
Keyword(s):  
Amino Acids ◽  
Absolute Configuration ◽  
Rapid Determination ◽  
Amino Alcohols ◽  
Enantioselective Synthesis ◽  
Widespread Occurrence ◽  
Chiral Compounds ◽  
New Methods ◽  
The Absolute

The widespread occurrence and significance of chiral compounds does not only require new methods for their enantioselective synthesis but also efficient tools that allow rapid determination of the absolute configuration,...

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