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Molecules 2017, 22(12), 2211; doi:10.3390/molecules22122211

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

1
Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary
2
Research Group of Stereochemistry of the Hungarian Academy of Sciences, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary
*
Authors to whom correspondence should be addressed.
Received: 3 November 2017 / Revised: 6 December 2017 / Accepted: 8 December 2017 / Published: 13 December 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

Efficient enzymatic resolutions are reported for the preparation of new eight-membered ring-fused enantiomeric β-amino acids [(1R,2S)-9 and (1S,2R)-9] and β-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 β-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. View Full-Text
Keywords: anatoxin-a; β-Amino acid; enzyme catalysis; β-Lactam; traceless activating group anatoxin-a; β-Amino acid; enzyme catalysis; β-Lactam; traceless activating group
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Forró, E.; Kiss, L.; Árva, J.; Fülöp, F. Efficient Enzymatic Routes for the Synthesis of New Eight-membered Cyclic β-Amino Acid and β-Lactam Enantiomers. Molecules 2017, 22, 2211.

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