Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine DOI Creative Commons
Paula Oroz, Claudio D. Navo, Alberto Avenoza

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14308 - 14318

Published: Sept. 30, 2022

Chemo- and diastereoselective 1,4-conjugate additions of anionic radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, carbon photolysis by catalytic photoredox process using simple method with metal-free photocatalyst provides exceptional yields selectivities at room temperature. Moreover, these offer an excellent starting point for synthesizing enantiomerically pure carbon-β-substituted unnatural α-amino acids (UAAs), which could have high potential applications in chemical biology.

Language: Английский

Chemoselective modification of chitosan with arginine and hydroxyproline: Development of antibacterial composite films for wound healing applications DOI

Sara Torkaman,

Seyed Heydar Mahmoudi Najafi, Alireza Ashori

et al.

International Journal of Biological Macromolecules, Journal Year: 2024, Volume and Issue: 282, P. 137081 - 137081

Published: Oct. 30, 2024

Language: Английский

Citations

1
NEW DRUGS ON THE PHARMACEUTICAL MARKET CONTAINING FLUORINE AND RESIDUES OF TAILOR-MADE AMINO ACIDS DOI Open Access
Jianlin Han, Alicja Wzorek, Gagan Dhawan

et al.

Ukrainian Chemistry Journal, Journal Year: 2024, Volume and Issue: 90(9), P. 31 - 56

Published: Oct. 25, 2024

This article profiles five newly drugs containing fluorine along with fragments of amino acids or their derivatives approved by the FDA in 2024. These pharmaceuticals include Voy­deya® (danicopan), Ojemda® (tovorafenib), Itovebi® (inavolisib), Scemblix® (asciminib), and Revuforj® (revumenib). For each drug, we discuss discovery, therapeutic areas application, detailed chemical synthesis.

Language: Английский

Citations

1
Asymmetric Synthesis of α‐Difluorinated β‐Amino Sulfones through Detrifluoroacetylative Mannich Reactions DOI
Ziyi Li, Nana Wang, Haibo Mei

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(21), P. 3035 - 3038

Published: May 5, 2021

Abstract Asymmetric detrifluoroacetylative Mannich reactions between α‐fluorinated arylsulfonyl gem ‐diols and fluoroalkyl imines have been developed under operationally convenient conditions. Varieties of are well tolerated with the corresponding α‐difluorinated β‐amino sulfone products generated in moderate to excellent yields as high diastereoselectivity. The reaction can be reproduced on gram‐scale uncompromised yield stereochemical outcome. synthetic value is demonstrated by two transformations means desulfonylation removal sulfinyl protecting‐group.

Language: Английский

Citations

7
Diaminopimelic acid and its analogues: Synthesis and biological perspective DOI
Bhaskar Chatterjee, Dhananjoy Mondal, Smritilekha Bera

et al.

Tetrahedron, Journal Year: 2021, Volume and Issue: 100, P. 132403 - 132403

Published: Aug. 13, 2021

Language: Английский

Citations

7
Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine DOI Creative Commons
Paula Oroz, Claudio D. Navo, Alberto Avenoza

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14308 - 14318

Published: Sept. 30, 2022

Chemo- and diastereoselective 1,4-conjugate additions of anionic radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, carbon photolysis by catalytic photoredox process using simple method with metal-free photocatalyst provides exceptional yields selectivities at room temperature. Moreover, these offer an excellent starting point for synthesizing enantiomerically pure carbon-β-substituted unnatural α-amino acids (UAAs), which could have high potential applications in chemical biology.

Language: Английский

Citations

5