Next Article in Journal
The Potential of Frog Skin-Derived Peptides for Development into Therapeutically-Valuable Immunomodulatory Agents
Previous Article in Journal
Incorporating Methyl and Phenyl Substituted Stannylene Units into Oligosilanes. The Influence on Optical Absorption Properties
Open AccessArticle

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.
Molecules 2017, 22(12), 2211; https://doi.org/10.3390/molecules22122211
Received: 3 November 2017 / Revised: 6 December 2017 / Accepted: 8 December 2017 / Published: 13 December 2017
(This article belongs to the Section Organic Chemistry)
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
Show Figures

Graphical abstract

MDPI and ACS Style

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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop