Separation of amino acid enantiomers and chiral amines using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase liquid chromatography

Einarsson, Stefán; Josefsson, Björn; Møller, Per; Sánchez, Domènec J.

doi:10.1021/ac00135a025

Cited by 332 publications

(90 citation statements)

References 28 publications

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“…HCI in 960 ml distilled water; pH 7.61 in an anaerobic chamber at 37 "C. Cell wall peptidoglycan was prepared and hydrolysed by the methods of Kawamoto et al (1981), and the amino acid composition was analysed with an automatic amino acid analyser (model 835; Hitachi). The neutral amino acid fraction was reacted with a chiral reagent [(+)-1-(9-fluoreny1)ethyl chloroformate] and used for HPLC as described by Einarsson & Josefsson (1987). DNA studies.…”

Section: Methodsmentioning

confidence: 99%

Phylogenetic and phenotypic evidence for the transfer of Eubacterium aerofaciens to the genus Collinsella as Collinsella aerofaciens gen. nov., comb. nov.

Kageyama

Benno

Nakase

1999

International Journal of Systematic and Evolutionary Microbiology

113

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Three strains of Eubacterium aerofaciens, JCM 10188T, JCM 7790 and JCM 7791, and 178 freshly isolated strains of the Eubacterium aerofaciens group from human faeces were characterized by biochemical tests, cell wall peptidoglycan type and 165 rRNA analysis. The Eubacterium aerofaciens group was divided into four groups by fermentation patterns of sucrose and cellobiose, and were further divided into 16 sub-groups by fermentation patterns of aesculin, salicin and amygdalin. All of the strains of the Eubacterium aerofaciens group were shown to be phylogenetically distantly related to Eubacterium limosum, which is the type species of genus Eubacterium. Eubacterium aerofaciens was shown to have a specific phylogenetic association with Coriobacterium glomerans. All the strains belonging to Eubacterium aerofaciens resembled Coriobacterium glomerans in possessing a high G+C content (60 mol%). Cell wall analysis, however, revealed the presence of different A4P (L-Ala)-D-GIu-L-Orn-L-Asp peptidoglycan types. Based on a 165 rRNA sequence divergence of greater than 9 % with Coriobacterium glomerans and the presence of a unique peptidoglycan type, a new genus, Collinsella, is proposed for Eubacterium aerofaciens, with one species, Collinsella aerofaciens. The type strain of Collinsella aerofaciens is JCM 101 88T.

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Section: Methodsmentioning

confidence: 99%

Phylogenetic and phenotypic evidence for the transfer of Eubacterium aerofaciens to the genus Collinsella as Collinsella aerofaciens gen. nov., comb. nov.

Kageyama

Benno

Nakase

1999

International Journal of Systematic and Evolutionary Microbiology

113

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“…30 -50% decomposition in methanol-water solution within 25 min when exposed to daylight [26]. Recently, 9-fluorenylmethyl chloroformate (FMOC) [32], 1-(9-fluorenyl)ethyl chloroformate, FLEC, [33], 6-oxy-(N-succinimidyl acetate)-9-(2-methoxycarbonyl)fluorescein [34] and 2-(9-anthyl)ethyl chloroformate, AEOC, [35] reagents have been used for the derivatization of amines, amino acids and peptides for chiral or non-chiral separation in LC or CE. Derivatization with these reagents produces derivatives with high molar absorption co-efficients in the ultraviolet as well as high response factors in LIF.…”

Section: Introductionmentioning

confidence: 99%

Application of 10‐ethyl‐acridine‐3‐sulfonyl chloride for HPLC determination of aliphatic amines in environmental water using fluorescence and APCI‐MS

You

Zhao

Sun

et al. 2009

J of Separation Science

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Original PaperApplication of 10-ethyl-acridine-3-sulfonyl chloride for HPLC determination of aliphatic amines in environmental water using fluorescence and APCI-MS A simple, sensitive method for the determination of aliphatic amines based on a sulfonylation reaction using 10-ethyl-acridine-3-sulfonyl chloride (EASC) as pre-column labeling reagent with fluorescence detection and APCI-MS identification has been developed. The labeled derivatives exhibited high stability and were enough to be efficiently analyzed by HPLC with an excitation maximum at k ex 270 nm and an emission maximum at k em 430 nm. Identification of derivatives was carried out by online post-column MS in positive-ion mode. Comparing with the widely used 5-dimethylaminonaphthalene-1-sulfonylchloride (Dansyl-Cl), EASC-amine derivatives not only exhibited high fluorescence but also exhibited excellent MS ionizable potential. Detection limits obtained from 0.10 pmol injection, at a S/N of 3, were 4.0 -12.7 fmol. The mean intra-and inter-assay precision for all aliphatic amine levels were a3.84 and 3.21%, respectively. Excellent linear responses were observed with coefficients of A0.9995.

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“…Derivatization methods have been reported with time requirements ranging from nearly instantaneous derivative formation with chloroformates with a bulky fluorene moiety [1,2], over one to two minutes requirement for treatment with the popular o.phthalaldehyde [3,4], to several minutes for derivatization with, e.g. phenylisothiocyanate [5,6].…”

mentioning

confidence: 99%

Amino acid derivatization and analysis in five minutes

Hušek

1991

FEBS Letters

140

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M~rch 1991Peer Hu,~ek Re.Y¢clreh In~titltte ¢~f l~ndt~crin¢~hJ~v. Nr)rndni ttid, ,~. CS.I i6 ~4 Pr~tx,e I. C:¢chn.~lnvakla Recei red 14 December 1990 A conv©nient method i~rmits amino acid ~par~ttion t~:t capillary Ba~ chroraalogr~aphy in mim~t¢~ =~ the ~uilable anal:clio form~ are preps, reel in tt¢~ond~,Amino ~tcid ~cparatio0; Oa~ chrom;llollr~ph?Among present methods of amino acid determination by both gas.liquid chromatography (GC) and reversedphase liquid chromatography (LC) after a precolumn derivatization, there is no one method which combines rapid sample pretreatment with rapid analysis of the derivatized forms. Because in LC analysis not all the active hydrogen-containing groups need to be treated and condensation of amino group is by far the prevailing approach, the average time for sample pretreatment is shorter than in GC.Derivatization methods have been reported with time requirements ranging from nearly instantaneous derivative formation with chloroformates with a bulky fluorene moiety [1,2], over one to two minutes requirement for treatment with the popular o.phthalaldehyde [3,4], to several minutes for derivatization with, e.g. phenylisothiocyanate [5,6]. With the last mentioned reagent the most rapid analysis of a complete mixture of protein amino acids was achieved, in 12 rain, which is the shortest time for determination of amino acids by LC. However, 60 min were necessary for physiological samples of amino acids [5,71 using the same method and the one hour analysis time can be considered as an average for LC performed amino acid analyses. Unlike GC analysis, use of capillary columns in LC lengthens the total time of a chromatographic run [8,9]. When considering GC in connection with amino acid analysis rather the opposite is to be expected; rapid analysis, but slow derivatization [10]. The widely used esterification-acylation procedures require on average one hour When summarizing criteria aiming to the establishment of a hypothetic, ideal procedure of amino acid determination, the following are required: (a) simple sample handling with possibly one reagent only, (b) ability to derivatize in aqueous medium, (c) an instate. taneous or very rapid reaction course proceeding at room temperature, (d) few-minute analysis with a good resolution and (e) low reagent and instrumental costs. Reviewing the nearly 40 years spent on amino acid methodology it would be rather unrealistic to expect fulfilment of all these requirements in one single procedure.But miracles happen. With the procedure reported here we are close to that ideal. The derivatization may no longer be the Achilles heel of GC. The chemical pretreatment of the sample determines the rapidity of analysis. This method takes about one minute and requires only five microliters of an inexpensive reagent. And the chemical conversion tolerates water, even dilute hydrochloric acid.The procedure is based on the treatment of aqueous amino acid solutions with ethyl chloroformate (ECF). An approach using isobutyl ehloroformate to the same purpo...

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Separation of amino acid enantiomers and chiral amines using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase liquid chromatography

Cited by 332 publications

References 28 publications

Phylogenetic and phenotypic evidence for the transfer of Eubacterium aerofaciens to the genus Collinsella as Collinsella aerofaciens gen. nov., comb. nov.

Phylogenetic and phenotypic evidence for the transfer of Eubacterium aerofaciens to the genus Collinsella as Collinsella aerofaciens gen. nov., comb. nov.

Application of 10‐ethyl‐acridine‐3‐sulfonyl chloride for HPLC determination of aliphatic amines in environmental water using fluorescence and APCI‐MS

Amino acid derivatization and analysis in five minutes

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