Guitot, Karine and Carboni, Stefano and Reiser, Oliver and Piarulli, Umberto (2009) Synthesis of (S)- and (R)-5-Oxo-piperazine-2-Carboxylic Acid and Its Application to Peptidomimetics. JOURNAL OF ORGANIC CHEMISTRY, 74 (21). pp. 8433-8436. ISSN 0022-3263,
Full text not available from this repository. (Request a copy)Abstract
A straightforward synthesis of (S)- and (R)-N-Boc-5-oxopiperazine-2-carboxylic acid is reported starting from L- or D-serine and ethyl glyoxylate. Those were evaluated as constituents in two tetrapeptides by studying their secondary Structure by H-1 NMR spectroscopy. In the case of Boc-Val-(S)-PCA-Gly-Leu-OMe, two readily interconverting conformations (in a 40%: 60% ratio) were observed, differing for the cis-trans isomerizaton of the tertiary amide bond, while Boc-Val-(R)-PCA-Gly-Lcu-OMe displayed an equilibrium between a gamma-turn and it type II beta-turn conformation.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | STEREOSELECTIVE TOTAL-SYNTHESIS; PIPECOLIC ACID; ASYMMETRIC-SYNTHESIS; PEPTIDE-BONDS; DERIVATIVES; ENANTIOMERS; RESOLUTION; ANALOGS; MODEL; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 02 Sep 2020 05:46 |
| Last Modified: | 02 Sep 2020 05:46 |
| URI: | https://pred.uni-regensburg.de/id/eprint/28139 |
Actions (login required)
 |
View Item |
