Document Detail


1-phenylethyl isocyanate is a powerful reagent for the chiral analysis of secondary alcohols and hydroxy fatty acids with remote stereogenic centres.
MedLine Citation:
PMID:  17697687     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
1-phenylethyl isocyanate (1-PEIC), a chiral derivatisation reagent for the resolution of secondary alcohols is a powerful tool to determine the configuration and enantiomeric excess of medium- to long-chain secondary alcohols by capillary gas chromatography. The separation of 1-phenylethylcarbamates (1-PECs) of secondary alcohols was systematically evaluated depending on the position of the stereogenic centre in the molecule, namely in alkanols (C(15)-C(18)), alkenols (C(15)-C(18)) and hydroxy fatty acids (C(14)-C(18)). The successful separation of the diastereomeric carbamates of (+/-)-heptadecan-7-ol or (+/-)-12-hydroxyoctadecanoic acid methyl ester by gas liquid chromatography demonstrates the unique separation power for 1-PECs for analytes with remote stereogenic centres. Saturated derivatives showed consistently higher resolution factors than the corresponding unsaturated derivatives.
Authors:
Andreas Habel; Dieter Spiteller; Wilhelm Boland
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-07-31
Journal Detail:
Title:  Journal of chromatography. A     Volume:  1165     ISSN:  0021-9673     ISO Abbreviation:  J Chromatogr A     Publication Date:  2007 Sep 
Date Detail:
Created Date:  2007-09-03     Completed Date:  2007-11-29     Revised Date:  2009-01-15    
Medline Journal Info:
Nlm Unique ID:  9318488     Medline TA:  J Chromatogr A     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  182-90     Citation Subset:  IM    
Affiliation:
Max Planck Institute for Chemical Ecology, Bioorganic Chemistry, 07745 Jena, Germany.
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MeSH Terms
Descriptor/Qualifier:
Alcohols / isolation & purification*
Fatty Acids / isolation & purification*
Gas Chromatography-Mass Spectrometry / methods*
Isocyanates / chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Alcohols; 0/Fatty Acids; 0/Isocyanates; 1943-82-4/phenylethyl isocyanate

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


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