Document Detail


Behavior and characteristics of the o-phthaldialdehyde derivatives of n-C6-C8 amines and phenylethylamines with four additive SH-containing reagents.
MedLine Citation:
PMID:  15058567     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The stability and characteristics of the C6-C8 n-aliphatic and phenylethylamines have been investigated as their o-phthaldialdehyde (OPA)/3-mercaptopropionic acid, OPA/N-acetyl-L-cysteine, OPA/2-mercaptoethanol and OPA/ethanethiol derivatives. Stoichiometric studies have been followed by photodiode array and fluorescence detection, simultaneously, while the composition of derivatives was confirmed by on line HPLC-electrospray ionization (ESI)-MS measurements. All four amines having in their original structure the NH2-CH2- moiety in accordance with the C1-C4 aliphatic, mono and diamines and amino acids of the same structure--furnished more than one OPA derivative: their initially formed isoindoles transform to further ones. Depending on the composition of the OPA reagents and on the pH of derivatizations different type of transformed species have been identified, in various proportions. Applying the OPA/SH additive reagent in the molar ratio of 1/3, favors the formation of one additional OPA molecule-containing isoindole, while using the OPA/SH additive (1/50) reagent resulted in the formation of one additional SH additive-containing species, identified and measured at the first time by HPLC. Transformation rate and stability of derivatives proved to be associated with the composition of the OPA reagent, with the type of the SH additive, with the pH of derivatizations, and, in selected cases also with the chain length of the amine. Results of stoichiometric and mechanism studies have been utilized to define optimum analytical conditions.
Authors:
R Hanczkó; D Kutlán; F Tóth; I Molnár-Perl
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of chromatography. A     Volume:  1031     ISSN:  0021-9673     ISO Abbreviation:  J Chromatogr A     Publication Date:  2004 Mar 
Date Detail:
Created Date:  2004-04-02     Completed Date:  2004-10-07     Revised Date:  2009-01-15    
Medline Journal Info:
Nlm Unique ID:  9318488     Medline TA:  J Chromatogr A     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  51-66     Citation Subset:  IM    
Affiliation:
Institute of Inorganic and Analytical Chemistry, L. Eötvös University, P.O. Box 32, H-1518 Budapest 112, Hungary.
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MeSH Terms
Descriptor/Qualifier:
Amines / chemistry*
Buffers
Data Display
Hydrogen-Ion Concentration
Indicators and Reagents
Mass Spectrometry
Phenethylamines / chemistry*
Reference Standards
Solutions
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Sulfhydryl Reagents / chemistry*
o-Phthalaldehyde / analogs & derivatives*,  chemistry*
Chemical
Reg. No./Substance:
0/Amines; 0/Buffers; 0/Indicators and Reagents; 0/Phenethylamines; 0/Solutions; 0/Sulfhydryl Reagents; 643-79-8/o-Phthalaldehyde

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