Linked Life Data

16078691

Source:http://linkedlifedata.com/resource/pubmed/id/16078691

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1-2
pubmed:dateCreated
2005-8-4
pubmed:abstractText
Cinchona alkaloid based chiral stationary phases (CSPs) were evaluated and compared for the enantiomer separation of a set of alpha-amino acid derivatives as selectands (SA), using ortho-phthalaldehyde (OPA), naphthalene-2,3-dicarboxaldehyde (NDA) and anthracene-2,3-dicarboxaldehyde (ADA) as reagents in the presence of acetonitrile. Protocols have been developed for the derivatization of most common amino acids in the absence of the usual thiol components (2-mercaptoethanol, mercaptosulphonic acid, sodium sulfite) under acidic and neutral conditions providing the corresponding isoindolin-1-one (phthalimidine) derivatives. They are stable for hours at various reaction conditions compared to thiol or sulfide modified isoindoles resulted by the OPA-thiol reaction type. Among the derivatizing agents, ADA afforded the highest retention factors (k) and for the majority of the analytes also resolution (Rs) and enantioselectivity (alpha) values (i.e. for tryptophan k1 = 23, Rs = 4.93 and alpha = 1.43). Structure variation of the CSPs and selector (SO), respectively indicates that steric arrangement around the binding cleft plays a major role in the enantiodiscriminating events. To provide more detailed information about the derivatization reaction itself, the proposed mechanism for the formation of the OPA derivative (isoindolin-l-one) was further evaluated by deuterium labeling and LC-MS analysis.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Aug
pubmed:issn
0021-9673
pubmed:author
pubmed:issnType
Print
pubmed:day
12
pubmed:volume
1083
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
80-8
pubmed:dateRevised
2009-1-15
pubmed:meshHeading
pubmed:year
2005
pubmed:articleTitle
Comparative study on the use of ortho-phthalaldehyde, naphthalene-2,3-dicarboxaldehyde and anthracene-2,3-dicarboxaldehyde reagents for alpha-amino acids followed by the enantiomer separation of the formed isoindolin-1-one derivatives using quinine-type chiral stationary phases.
pubmed:affiliation
Institute of Analytical Chemistry and Food Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, Austria.
pubmed:publicationType
Journal Article, Comparative Study, Research Support, Non-U.S. Gov't