Sequential arrangement of gamma-valerolactone enantiomers enclathrated in cholic acid channels as studied by 13C solid-state NMR: elucidation of the optical resolution mechanism

Journal of the American Chemical Society
Shinji NakamuraTakehiko Terao

Abstract

The mechanism of the optical resolution of gamma-valerolactone (VAL) enantiomers by enclathration in cholic acid (CA) channels was investigated. 13C cross-polarization magic-angle spinning spectra of CA/VAL inclusion compounds show four methyl 13C peaks of VAL with different intensities depending on the enantiomeric ratios. The four peaks were assigned to the inner and end (S)-(-)-enantiomers (S) in the S domain and the inner and end (R)-(+)-enantiomers (R). The relative intensities of the four methyl 13C peaks cannot be explained by the random process model for inclusion but are successfully reproduced by assuming the first-order Markov process, in which the inclusion probabilities of S and R depend on which enantiomer has precedingly entered the CA channel. The probability p(S/S) that two S enantiomers successively enter a channel is thus found to be 83%, and p(R/R) is 50%. The large probability of p(S/S) indicates that once an S enantiomer enters a channel, it become easy for other S enantiomers to successively enter the channel, and thus the large enantiomeric excess of S is obtained. The inclusion probabilities of S and R were confirmed by 1D 13C-13C polarization-transfer experiments among the four methyl carbons of VAL in...Continue Reading

Citations

Oct 26, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mikiji MiyataIchiro Hisaki
Oct 27, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Arto ValkonenReijo Kauppinen
Dec 3, 2014·Colloids and Surfaces. B, Biointerfaces·Meng-Xin HuZhi-Kang Xu
Sep 11, 2009·Chirality·Olga BortoliniMarco Fogagnolo
Jul 22, 2008·Steroids·Arto ValkonenErkki Kolehmainen

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