Synthesis of Amino-Acid-Based Nitroalkenes

Fatty-acid-based nitroalkenes have recently received great attention because of their bioactivities. On the contrary, peptide- or amino-acid-based nitroalkenes have been scarcely explored so far, although they may exhibit interesting biological properties, for example, as enzyme inhibitors. In this...

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Bibliographic Details
Published in:Organics (Basel) 2022-06, Vol.3 (2), p.137-149
Main Authors: Gerogianni, Velisaria-Eleni, Koutoulogenis, Giorgos S., Gerokonstantis, Dimitrios Triantafyllos, Kokotos, George
Format: Article
Language:English
Subjects:
Alcohol
Amino acids
Aqueous solutions
Chromatography
Drugs
elimination reaction
Fatty acids
Henry reaction
Methods
Natural products
nitroalkenes
Peptides
Potassium
Severe acute respiratory syndrome coronavirus 2
Spectrum analysis
synthesis
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Summary:Fatty-acid-based nitroalkenes have recently received great attention because of their bioactivities. On the contrary, peptide- or amino-acid-based nitroalkenes have been scarcely explored so far, although they may exhibit interesting biological properties, for example, as enzyme inhibitors. In this work, we study protocols for the efficient synthesis of nitroalkenes based on natural amino acids. A variety of N-protected amino alcohols and Weinreb amides, derived from α-amino acids, were converted to the corresponding N-protected amino aldehydes, and, through a Henry reaction with nitroalkanes, produced the corresponding nitro alcohols. The subsequent elimination reaction led to the (E)-isomer of amino-acid-based nitroalkenes in moderate to high yields.
ISSN:2673-401X
2673-401X
DOI:10.3390/org3020011