Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications

被引：0

作者：

Picois, Nathan ^{[1
,2
]}

Boutahri, Yazid ^{[1
,2
]}

Milbeo, Pierre ^{[1
,2
]}

Zanato, Chiara ^{[1
,2
]}

Lensen, Nathalie ^{[1
,2
]}

Chaume, Gregory ^{[1
,2
]}

Brigaud, Thierry ^{[1
,2
]}

机构：

[1] CY Cergy Paris Univ, CNRS, BioCIS UMR 8076, F-95000 Cergy Pontoise, France

[2] Univ Paris Saclay, CNRS, BioCIS UMR 8076, F-91400 Orsay, France

来源：

MOLECULES | 2024年 / 29卷 / 06期

关键词：

amino acids; asymmetric synthesis; fluorinated compounds; peptides; medicinal chemistry; chemical biology; ZINC/BINOL-CATALYZED ALKYNYLATION; POSITRON-EMISSION-TOMOGRAPHY; C-H BONDS; BUILDING-BLOCKS; DIASTEREOSELECTIVE SYNTHESIS; TRIFLUOROMETHYLATED PROLINE; DIFLUOROMETHYL AMINES; BIOLOGICAL EVALUATION; PEPTIDE; DERIVATIVES;

D O I：

10.3390/molecules29061408

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Due to the specific properties provided by fluorine atoms to biomolecules, amino acids with fluorinated side chains are of great interest for medicinal chemistry and chemical biology. Among them, alpha-fluoroalkyl-alpha-amino acids constitute a unique class of compounds. In this review, we outline the strategies adopted for their syntheses in enantiopure or enantioenriched forms and their incorporation into peptides. We then describe the consequences of the introduction of fluorine atoms in these compounds for the modulation of their hydrophobicity and the control of their conformation. Emerging applications are presented in the areas of enzyme inhibition, medicinal chemistry, hydrolytic stability of peptides, antimicrobial peptides, PET, and 19F NMR probes.

引用

页数：42

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