Reversed-phase liquid chromatographic resolution of diastereomers of protein and non-protein amino acids prepared with newly synthesized chiral derivatizing reagents based on cyanuric chloride

Amino Acids

Volumn 40, Issue 2, 2011, Pages 403-409

  Bhushan, Ravi ^a   Agarwal, Charu ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

Author keywords

Amino acids; Cyanuric chloride; Indirect resolution; Reversed phase liquid chromatography

Indexed keywords

AMINO ACID; CYANURIC ACID; CYANURIC CHLORIDE; N (4 CHLORO 6 PIPERIDINYL[1,3,5]TRIAZINE 2 YL)LEUCINAMIDE; N (4 CHLORO 6 PIPERIDINYL[1,3,5]TRIAZINE 2 YL)LEUCINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; DERIVATIZATION; DIASTEREOISOMER; HYDROPHOBICITY; PRIORITY JOURNAL; PROTEIN ANALYSIS; REVERSED PHASE LIQUID CHROMATOGRAPHY; SEPARATION TECHNIQUE; SYNTHESIS; VALIDATION PROCESS;

AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, REVERSE-PHASE; PROTEINS; STEREOISOMERISM; TRIAZINES;

EID: 78751579279     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0650-z     Document Type: Article

References (15)

1. HMS Ali R Pätzold H Brückner 2010 Gas chromatographic determination of amino acid enantiomers in bottled and aged wines Amino Acids 38 951 958 1:CAS:528:DC%2BC3cXjt1eqsrg%3D 10.1007/s00726-009-0304-1 19504228
2. C B'Hymer M Montes-Bayon JA Caruso 2003 Marfey's reagent: past, present, and future uses of 1-fluoro-2, 4-dinitrophenyl-5-l-alanine amide J Sep Sci 26 7 19 10.1002/jssc.200390019 (Pubitemid 36253745)
3. Bhushan R, Agarwal C (2010) Application of (S)-N-(4-nitrophenoxycarbonyl) phenylalanine methoxyethyl ester as a chiral derivatizing reagent for reversed-phase high-performance liquid chromatographic separation of diastereomers of amino alcohols, non-protein amino acids and PenA. Amino Acids. doi: 10.1007/s00726-010-0472-z
4. R Bhushan H Brückner 2004 Marfey's reagent for chiral amino acid analysis: a review Amino Acids 27 231 247 1:CAS:528:DC%2BD2cXhtVGgt7vO 10.1007/s00726-004-0118-0 15503232 (Pubitemid 40110064)
5. R Bhushan V Kumar 2008 Indirect enantioseparation of α-amino acids by reversed-phase liquid chromatography using new chiral derivatizing reagents synthesized from s-triazine chloride J Chromatogr A 1201 35 42 1:CAS:528:DC%2BD1cXosFSnsb0%3D 10.1016/j.chroma.2008.05.087 18556008
6. R Bhushan V Kumar S Tanwar 2009 Chromatographic separation of enantiomers of non-protein α-amino acids after derivatization with Marfey's reagent and its four variants Amino Acids 36 571 579 1:CAS:528:DC%2BD1MXisVOktb0%3D 10.1007/s00726-008-0135-5 18612776
7. H Brückner C Keller-Hoehl 1990 HPLC separation of dl-amino acids derivatized with N2-(5-fluoro-2, 4-dinitrophenyl)-l-amino acid amides Chromatographia 30 621 629 10.1007/BF02269735
8. H Brückner M Wachsmann 1996 Liquid chromatographic separation of amino acid enantiomers on a silica-bonded chiral s-triazine column J Chromatogr 728 447 454 10.1016/0021-9673(95)01204-4 (Pubitemid 26143296)
9. H Brückner M Wachsmann 2003 Design of chiral monochloro-s-triazine reagents for the liquid chromatographic separation of amino acid enantiomers J Chromatogr 998 73 82 10.1016/S0021-9673(03)00638-1 (Pubitemid 36629462)
10. M De Zotti F Damato F Formaggio M Cirsma E Schievano S Mammi B Kaptein QB Broxterman PJ Felock DJ Hazuda SB Singh J Kirschbaum H Brückner C Toniolo 2010 Total synthesis, characterization, and conformational analysis of the naturally occurring hexadecapeptide integramide A and a diastereomer Chem Eur J 16 316 327 10.1002/chem.200900945
11. K Fujii Y Ikai T Mayumi H Oka M Suzuki K Harada 1997 A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: elucidation of limitations of Marfey's method and of its separation mechanism Anal Chem 69 3346 3352 1:CAS:528:DyaK2sXkslKmtb4%3D 10.1021/ac9701795 (Pubitemid 27357548)
12. Hunt S (1985) In: Barrett GC (ed) Chemistry and Biochemistry of the amino acids. Chapman and Hall, London, p 55
13. J-Y Lin M-H Yang 1993 High-performance liquid chromatographic separation of enantiomeric amino acids on bis[carbamoyl(alkyl)methylamino]-6-chloro-s- triazine-derived chiral stationary phases J Chromatogr 644 277 283 1:CAS:528:DyaK3sXmvVGnu7Y%3D 10.1016/0021-9673(93)80709-H (Pubitemid 23242459)
14. P Marfey 1984 Determination of d-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene Carlsberg Res Comm 49 591 596 1:CAS:528:DyaL2MXhs1Oisbw%3D 10.1007/BF02908688
15. M Wachsmann H Brückner 1998 Ligand-exchange chromatographic separation of dl-amino acids on aminopropylsilica-bonded chiral s-triazines Chromatographia 47 637 642 1:CAS:528:DyaK1cXkvVynu7k%3D 10.1007/BF02467446 (Pubitemid 28307803)