Synthesis and application of new chiral variants of Marfey's reagent for liquid chromatographic separation of the enantiomers of α -amino acids

• Autorzy: Bhushan R. , Kumar V.
• Języki publikacji: EN

Abstrakty

EN

Two new structural variants of Marfey's reagent (1-fluoro-2,4-dinitrophenyl-5-L -alaninamide, FDNP-L -Ala-NH 2 ) were synthesized by nucleophilic substitution of one fluorine atom in 1,5-difluoro-2,4-dinitrobenzene (DFDNB) by L -methioninamide or D -phenylglycinamide. The new variants FDNP-L -Met-NH 2 and FDNP-D -Phg-NH 2 were characterized and used for derivatization of twenty-six α-amino acids. The resulting diastereomeric derivatives were separated on a reversed-phase C ₁₈ HPLC column using a linear gradient of acetonitrile and aqueous trifluoroacetic acid (TFA) and the results were compared with those obtained by use of Marfey's reagent. To determine and establish the efficiency of both the new variants, separation results were compared for diastereomers of five representative amino acids (Ala, Phe, Ser, Asp, and Asn) prepared with MR, FDNP-_L-Phe-NH 2 , FDNP-_L -Val-NH 2 , FDNP-_L -Leu-NH 2 , and FDNP-_L -Pro-NH 2 , experiments being performed under identical conditions. Both the new chiral reagents enabled better separation of the diastereomers than Marfey's reagent for most of the amino acids. The reagent FDNP-_D -Phg-NH 2 enabled excellent separation for serine and asparagine whereas other reagents failed or provided poor results.

Słowa kluczowe

EN

chiral separation; alpha-amino acids; Marfey's reagent; structural variants; FDNP-L-Met-NH 2; FDNP-D-Phg-NH 2; RP-HPLC

• Wydawca: University of Silesia in Katowice ; Akademiai Kiado
• Czasopismo: Acta Chromatographica
• Rocznik: 2008
• Tom: Vol. 20, no. 3
• Strony: 329--347
• Opis fizyczny: Bibliogr. 21 poz., rys., tab.

Twórcy

autor

Bhushan R.

autor

Kumar V.

• Indian Institute of Technology Roorkee Department of Chemistry Roorkee 247 667 India [e-mail],

Bibliografia

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