Efficient Enzymatic Routes for the Synthesis of New Eight-membered Cyclic β-Amino Acid and β-Lactam Enantiomers

Forró, Enikő and Kiss, Loránd and Árva, Judit and Fülöp, Ferenc (2017) Efficient Enzymatic Routes for the Synthesis of New Eight-membered Cyclic β-Amino Acid and β-Lactam Enantiomers. MOLECULES, 22 (12). ISSN 1420-3049

Preview

Text forro_molecules_2017.pdf Download (1MB) | Preview

Abstract

Efficient enzymatic resolutions are reported for the preparation of new eight-membered ring-fused enantiomeric -amino acids [(1R,2S)-9 and (1S,2R)-9] and -lactams [(1S,8R)-3, (1R,8S)-3 (1S,8R)-4 and (1R,8S)-7], through asymmetric acylation of (+/-)-4 (E > 100) or enantioselective hydrolysis (E > 200) of the corresponding inactivated (+/-)-3 or activated (+/-)-4 -lactams, catalyzed by PSIM or CAL-B in an organic solvent. CAL-B-catalyzed ring cleavage of (+/-)-6 (E > 200) resulted in the unreacted (1S,8R)-6, potential intermediate for the synthesis of enantiomeric anatoxin-a. The best strategies, in view of E, reaction rate and product yields, which underline the importance of substrate engineering, are highlighted.

Actions (login required)

Edit Item