A Nonempirical Method Using LC/MS for Determination of the Absolute Configuration of Constituent Amino Acids in a Peptide:  Combination of Marfey's Method with Mass Spectrometry and Its Practical Application

Fujii, Kiyonaga; Ikai, Yoshitomo; Oka, Hisao; Suzuki, and Makoto; Harada, Kenichi

doi:10.1021/ac970289b

Cited by 408 publications

(462 citation statements)

References 17 publications

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“…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.…”

Section: General Properties Of the Wap-8294a Componentsmentioning

confidence: 99%

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

Kato

Hirata

Ohashi³

et al. 2011

J Antibiot

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The anti-MRSA antibiotic, WAP-8294A, was isolated from the fermentation broth of Lysobacter sp. The major component,and 2 mol of L-Ser, D-Orn and D-3-hydroxy-7-Me-octanoic acid. The structure of the WAP-8294A2 was mainly determined as a cyclic depsipeptide by 2D NMR experiments. However, it was difficult to use the NMR experiment to determine the minor components, A1, A4 and Ax13, isolated in small amounts. In the present study, ESI MS/MS was applied to the structure elucidation of these minor components. The structures of these minor components were determined on the basis of the fragmentation pattern of the product ions of WAP-8294A2 in the ESI MS/MS. As a result, it was confirmed that A1 and A4 had the same amino acid sequence as A2, while A1 and A4 had the 3-OH-octanoic acid and 3-OH-8-Me-nonanoic acid, respectively, in the place of the 3-OH-7-Meoctanoic acid in A2. In the structure of Ax13, it was found that Gly of A2 was changed to b-Ala of Ax13.

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Section: General Properties Of the Wap-8294a Componentsmentioning

confidence: 99%

“…14,15 Each 500 mg sample was hydrolyzed at 110 1C for 1 h with 500 ml of 6 M HCl. This solution was divided into two portions, and each portion was derivatized with L-or D-FDLA.…”

Section: Determination Of Chirality Of Amino Acidmentioning

confidence: 99%

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

Kato

Hirata

Ohashi³

et al. 2011

J Antibiot

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“…This method is named the "advanced Marfey's methods". 16,17) First of all, a peptide is subjected to the usual acidic hydrolysis to obtain each constituent amino acid. The reaction product is divided into two portions (samples 1 and 2), one of which is derivatized with L-FDLA (1-fluoro-2,4-dinitrophenylleucinamide) and another is derivatized with D-FDLA.…”

Section: How To Isolate Desired Compounds and To Determine Their Strumentioning

confidence: 99%

Production of Secondary Metabolites by Freshwater Cyanobacteria

Harada

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Freshwater cyanobacteria produce lethal toxins such as microcystins and anatoxins. During the purification of microcystins in bloom samples we found that a toxic cyanobacterium produced not only microcystins but also other types-peptides in early 1990. Since then we have isolated approximately thirty peptides from freshwater cyanobacteria. In this manuscript we focused on the following topics concerning the isolated peptides: 1) how to isolate desired compounds and to determine their structures, 2) structural classification of isolated compounds, 3) isolation of similar peptides from laboratory strains and bloom materials, 4) structurally related peptides from freshwater and marine origins, 5) b b-amino acid containing peptides from cyanobacteria, 6) comprehensive analysis system for the biosynthetic study of peptides produced by cyanobacteria, 7) biological activities of isolated compounds.

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“…Pipecolic acid and lysine were labeled with 14) and the L-FDLA derivatives of pipecolic acid and lysine were analyzed by HPLC on a YMC-Pack s-5 60A ODS (4.6×150 mm) column maintained at 359 C using a acetonitrile concentration gradient in 1z acetic acid aqueous solution from 40z to 80z for 20 minutes with a ‰ow rate of 1.0 ml per minute. The derivatives were detected by UV-monitoring at 340 nm.…”

Section: )mentioning

confidence: 99%

Biotransformation ofL-Lysine toL-Pipecolic Acid Catalyzed byL-Lysine 6-Aminotransferase and Pyrroline-5-carboxylate Reductase

Fujii

Mukaihara

Agematu

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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A Nonempirical Method Using LC/MS for Determination of the Absolute Configuration of Constituent Amino Acids in a Peptide: Combination of Marfey's Method with Mass Spectrometry and Its Practical Application

Cited by 408 publications

References 17 publications

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

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

Production of Secondary Metabolites by Freshwater Cyanobacteria

Biotransformation ofL-Lysine toL-Pipecolic Acid Catalyzed byL-Lysine 6-Aminotransferase and Pyrroline-5-carboxylate Reductase

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