Application of d,l-FDLA derivatization to determination of absolute configuration of constituent amino acids in peptide by advanced Marfey's method

Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757

“…These derivatives were also analyzed by LC/MS at m/ z 414 and 459 in the positive ion mode (Figure 4). 15 Using the DL-FDLA method, 16 it was possible to conclude that the two amino acids have the L configuration. It was also found that the intense peak observed at around 4 min shown in Figure 3 has a molecular weight of 616.…”

A new anti-MRSA antibiotic complex, WAP-8294A II. Structure characterization of minor components by ESI LCMS and MS/MS

“…Their absolute configurations were determined by amino acid analysis using the advanced Marfey's method. [14][15][16] The mass chromatograms of the amino acid derivatives from 1 and 4 using ESI-LC/MS are shown in Figures 2A and B Table 1.…”

“…This solution was divided into two portions, and each portion was derivatized with L-or D-FDLA. 16 Each solution was then evaporated to dryness, and the residue was dissolved in 75 ml of water and 25 ml of methanol. To each amino acid solution, 20 ml of 1 M sodium bicarbonate and then 100 ml of 1% L-or D-FDLA in acetone were added.…”

Optical Resolution of 1,2-Diamino Compounds Using Advanced Marfey's Method

“…As a result of these experiments, the elution order was as follows: (S,S), (R,R), and meso, and the behavior was finally confirmed by the 9A-FDLA method. 4) 3.3 Proposed method for determination of the absolute configuration of 1,2-diaminoethane compounds The elution behavior of 1,2-diphenylethylene-1,2-diamine derivatized with A-and 9-FDLA was carefully investigated, and the following pattern was found: 1) (S,S)-isomer-A-DLA derivative is eluted prior to the (R,R)-isomer-A-DLA derivative; 2) The (R,R)-and mesoisomers-A-DLA derivatives are closely eluted; 3) There is no di#erence between the retention time of both the A-and 9-DLA derivatives of the meso-isomer; 4) This regularity is fundamentally consistent with that of the diamino acids, such as diaminopimelic acid and diaminosuccinic acid except for the elution behavior of the meso-isomer. In this case, because the (S,S)-isomer corresponds to the (A,A)-isomer of the diamino acid, the separation behavior can be probably explained using the separation mechanism for advanced Marfey's method.…”

“…Advanced Marfey's method in combination with chemical racemization and 9A-FDLA methods 4) was further used to determine the absolute configuration of several diamino acids including A 2 pm with a "meso" configuration. 5) Based on the elution order, the absolute configuration was definitely determined.…”