Cabrele, Chiara and Clerici, F. and Gandolfi, R. and Gelmi, Maria Luisa and Molinari, F. and Pellegrino, S. (2006) Chemoenzymatic resolution of epimeric cis 3-carboxycyclopentylglycine derivatives. TETRAHEDRON, 62 (15). pp. 3502-3508. ISSN 0040-4020,
Full text not available from this repository. (Request a copy)Abstract
Epimeric 3-carboxycyclopentylglycines (+)-10/(-)-10 and (+)-11/(-)-11 were efficiently prepared by the way of a sequence of D\iels-Alder and retro-Claisen reactions. The synthesis incorporates a concise and inexpensive chemoenzymatic resolution of racemic compounds 4,5a, the N,O-protected derivatives of amino acids 10,11. Systematic screening with different enzymes and microorganisms was performed to select a very efficient catalyst for the separation of the racemic mixtures. The reaction conditions allowing deprotection of both ester and amino functions and to avoiding epimerization processes were studied. Enantiomers (i.e., (+)-10/(-)-10 and (+)-11/(-)-11) were obtained in high enantiopurity. The absolute configuration of all stereocenters was unequivocally assigned. (c) 2006 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ALPHA-AMINOADIPIC ACID; AMINO-ACIDS; PENICILLIN; ESTERS; 3-carboxycyclopentylglycines; enzymatic resolution; Aspergillus melleus; absolute configuration |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Dr. Chiara Cabrele |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 16 Feb 2021 10:02 |
| Last Modified: | 16 Feb 2021 10:02 |
| URI: | https://pred.uni-regensburg.de/id/eprint/34698 |
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