PREPARATION OF RACEMIC 2r-CARBOXY-TRANS, TRANS-3, 4-DIDEUTERO-PYRROLIDINE (DL-TRANS, TRANS-3, 4-DIDEUTERO-PROLINE) AND UNAMBIGUOUS ASSIGNMENT OF PROTONS IN THE 1H N.M.R. SPECTRUM OF PROLINE
- 12 January 2009
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 14 (5), 445-450
- https://doi.org/10.1111/j.1399-3011.1979.tb01955.x
Abstract
Racemic trans, trans-3,4-dideutero proline was prepared by catalytic deuteration of 3-pyrroline-2-carboxylic acid. The stereospecificity of the reduction (i.e., trans to the carboxylic group) was ascertained after transformation of the dideutero compound into the diketopiperazide c/Pro, Aib/[proline, .alpha.-aminoisobutyric acid-diketopiperazide], for which unambiguous proton assignments in the 1H NMR spectrum were obtained previously. The identification of the configuration of the dideuteroproline allowed for the affirmation of the correctness of proton assignments as previously proposed in literature.Keywords
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