Document Detail


Gas chromatographic resolution of enantiomeric amphetamines and related amines. II. Effects of cyclic structures on diastereomer and enantiomer resolution.
MedLine Citation:
PMID:  1202044     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Proline and other cyclic amino acids were used as acylated acid chlorides for the resolution of enantiomers of amphentamine and related amines as diastereomers by gas chromatography. Variation of ring size or incorporation of a heteroatom into the ring of the cyclic resolving agent changed retention times and separation factors, depending on the racemic amine derivatized. Separations were achieved on a short, packed Carbowax 20M column. Because N-trifluoroacetyl L-prolyl chloride has proved especially effective for derivatization of amine enantiomers to give diastereomers which often may be resolved by gas chromatography, the proline ring was incorporated into a new optically active stationary phase. For the enantiomeric derivatives examined, the new proline ester phase gave separations essentially equivalent to those obtained on the commercially available phase, carbonyl bis-(L-valine isopropyl ester). The fact that resolution was achieved on the new phase is evidence that, as has been previously suggested, the ester carbonyls of this type of phase are the significant sites of interaction with the antipodes undergoing separation.
Authors:
R W Souter
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of chromatography     Volume:  114     ISSN:  -     ISO Abbreviation:  J. Chromatogr.     Publication Date:  1975 Nov 
Date Detail:
Created Date:  1976-03-01     Completed Date:  1976-03-01     Revised Date:  2013-12-13    
Medline Journal Info:
Nlm Unique ID:  0427043     Medline TA:  J Chromatogr     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  307-13     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Acylation
Amino Acids / analysis
Amphetamines / analysis*
Chromatography, Gas*
Cyclization
Indicators and Reagents
Proline
Stereoisomerism
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Amphetamines; 0/Indicators and Reagents; 9DLQ4CIU6V/Proline

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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