NDLI: Application of cyanuric chloride-based six new chiral derivatizing reagents having amino acids and amino acid amides as chiral auxiliaries for enantioresolution of proteinogenic amino acids by reversed-phase high-performance liquid chromatography

Content Provider	Springer Nature Link
Author	Bhushan, Ravi Dixit, Shuchi
Copyright Year	2011
Abstract	Six dichloro-s-triazine (DCT) reagents having l-Leu, d-Phg, l-Val, l-Met, l-Ala and l-Met-NH2 as chiral auxiliaries in cyanuric chloride were introduced for enantioseparation of 13 proteinogenic amino acids. Four other DCTs and six monochloro-s-triazine (MCT) reagents having amino acid amides as chiral auxiliaries were also synthesized. These 16 chiral derivatizing reagents (CDRs) were used for synthesis of diastereomers of all the 13 analytes using microwave irradiation, which were resolved by reversed-phase high-performance liquid chromatography (RP-HPLC) using C18 column and gradient eluting mixture of aqueous TFA and acetonitrile with UV detection at 230 nm. It required only 60–90 s for derivatization using microwave irradiation. Better resolution and lower retention times were observed for the diastereomers prepared with CDRs having amino acids as chiral auxiliaries as compared to counterparts prepared with reagents having amino acid amides as chiral auxiliaries. As the best resolution of all the 13 analytes was observed for their diastereomers prepared using the DCT reagent having l-Leu as chiral auxiliary, this CDR was further employed for derivatization of Lys, Tyr, His and Arg followed by RP-HPLC analysis of resulting diastereomers. The results are discussed in light of acid and amide groups of chiral auxiliaries constituting CDRs, electronegativities of the atoms of achiral moieties constituting CDRs and hydrophobicities of side chains of amino acids constituting CDRs and analytes.
Starting Page	1371
Ending Page	1378
Page Count	8
File Format	PDF
ISSN	09394451
Journal	Amino Acids
Volume Number	42
Issue Number	4
e-ISSN	14382199
Language	English
Publisher	Springer Vienna
Publisher Date	2011-01-19
Publisher Place	Vienna
Access Restriction	Subscribed
Subject Keyword	Cyanuric chloride Amino acids Chiral derivatizing reagents Reversed-phase high-performance liquid chromatographic separation Enantioseparation Neurobiology Proteomics Biochemical Engineering Life Sciences Biochemistry Analytical Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Clinical Biochemistry

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