ISSN:
0025-116X
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The interactions of the hydrobromides of (R)- and (S)-alanine-N-methylanilides (1) with 24-, 27- and 36-membered ring pseudopeptides (H-24, H-27 and H-36, respectively) derived from glycine and (2S,3′ S)-4-methyl-2-(2′-oxo-3′-isobutyl-1′-piperazinyl)pentanoic acid were studied by means of 1H and 13C NMR measurements in CDCl3. It was found from these results that H-24 and H-27 distinguished (R)- and (S)-isomers of 1, while H-36 did not entirely. Moreover, the enantioface-differentiating abilities of these cyclic peptides were investigated by means of 1H NMR measurements in CDCI3 using (R)- and (S)-1-phenylethylammonium and (R)- and (S)-p-methoxy-1-phenylethylammonium bromides as the substrates, showing that the enantio-selectivity of H-36 is superior to those of H-24 and H-27. Also, the chiral recognition ability of H-24 for the hydrochlorides of (R)- and (S)-alanine (Ala), -leucine (Leu), -methionine (Met), -phenylalanine (Phe), -proline (Pro) and -valine (Val) methyl esters were examined by 1H and 13C NMR measurements in CDCl3. Among these hydrochlorides, HCl · Phe—OCH3 was distinguished more effectively with H-24.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1993.021940707
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