Chiral solute–solvent systems. Selective interaction between N-dodecanoyl-L-valine amides and N-trifluoroacetyl esters of the enantiomers of 2-aminoalkan-1-ols and α-, β-, and γ-amino-acids

doi:10.1039/P29790001230

Paper

Chiral solute–solvent systems. Selective interaction between N-dodecanoyl-L-valine amides and N-trifluoroacetyl esters of the enantiomers of 2-aminoalkan-1-ols and α-, β-, and γ-amino-acids

Published 1979 · B. Feibush, A. Balan, B. Altman

Journal of The Chemical Society-perkin Transactions 1

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Abstract

Optically active 2-aminoalkan-1-ols in the form of their O-acyl-N-trifluoroacetyl derivatives have been resolved by g.l.c. with N-dodecanoyl-L-valine 6-undecylamide (1) as the stationary phase. A bulky O-acyl group substantially facilitates resolution. Resolutions of the N-trifluoroacetyl-esters of α-, β-, and γ-amino-acids on diamide phases are also reported. The order of emergence of the derivatives of the 2-aminoalkan-1-ols and the γ-amino-acids is D after the L-isomer, i.e., the reverse of that found for the α-amino-acids.The mechanism of resolution is discussed on the basis of association complexes involving the formation of two hydrogen bonds between the solutes and the solvent.

Study Snapshot

N-dodecanoyl-L-valine amides and N-trifluoroacetyl esters of 2-aminoalkan-1-ols can selectively resolve chiral solute-solvent systems, with the mechanism involving two hydrogen bonds between solutes and solvent

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Chiral solute–solvent systems. Selective interaction between N-dodecanoyl-L-valine amides and N-trifluoroacetyl esters of the enantiomers of 2-aminoalkan-1-ols and α-, β-, and γ-amino-acids

References

Citations

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