Determination ofd-Amino Acids Labeled with Fluorescent Chiral Reagents,R(−)- andS(+)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7- (N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazoles, in Biological and Food Samples by Liquid Chromatography

Jin, Dongri; Miyahara, Taketsune; Oe, Tomoyuki; Toyo’oka, Toshimasa

doi:10.1006/abio.1998.3090

Cited by 76 publications

(33 citation statements)

References 31 publications

(34 reference statements)

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“…The major organic components of human urine include urea, uric acid, and creatinine (44). Free amino acids are also present in urine, including all of the known amino acid substrates of CycA in the following concentration ranges: L-alanine (0.26 to 9.1 g/ml) (28-30), ␤-alanine (0.2 to 1.0 g/ml) (45), D-serine (1 to 39 g/ml) (28,30,46), D-alanine (0.004 to 7.5 g/ml) (28)(29)(30), and glycine (0.34 to 7.5 g/ml) (31,32). The presence of CycA substrates in human urine, and possibly LB, suggests E. coli most likely does not transport DCS through CycA due to substrate competition.…”

Section: Discussionmentioning

confidence: 99%

Characterization of Escherichia coli d -Cycloserine Transport and Resistant Mutants

2013

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b D-Cycloserine (DCS) is a broad-spectrum antibiotic that inhibits D-alanine ligase and alanine racemase activity. When Escherichia coli K-12 or CFT073 is grown in minimal glucose or glycerol medium, CycA transports DCS into the cell. E. coli K-12 cycA and CFT073 cycA mutant strains display increased DCS resistance when grown in minimal medium. However, the cycA mutants exhibit no change in DCS sensitivity compared to their parental strains when grown in LB (CFT073 and K-12) or human urine (CFT073 only). These data suggest that cycA does not participate in DCS sensitivity when strains are grown in a non-minimal medium. The small RNA GvcB acts as a negative regulator of E. coli K-12 cycA expression when grown in LB. Three E. coli K-12 gcvB mutant strains failed to demonstrate a change in DCS sensitivity when grown in LB. This further suggests a limited role for cycA in DCS sensitivity. To aid in the identification of E. coli genes involved in DCS sensitivity when grown on complex media, the Keio K-12 mutant collection was screened for DCS-resistant strains. dadA, pnp, ubiE, ubiF, ubiG, ubiH, and ubiX mutant strains showed elevated DCS resistance. The phenotypes associated with these mutants were used to further define three previously characterized E. coli DCS-resistant strains (316, 444, D -Cycloserine (DCS) is a broad-spectrum antibiotic produced by Streptomyces garyphalus, Streptomyces orchidaceus, andStreptomyces lavendulae. DCS is a cyclic, structural analog of D-alanine that inhibits alanine racemase and D-alanine ligase activity (1, 2). Inactivation of these enzymes results in a failure to produce mature peptidoglycan and an increased susceptibility to osmotic lysis. DCS is occasionally used as a second-line drug in the treatment of multidrug-resistant Mycobacterium tuberculosis infections (3, 4).DCS is not commonly used in chemotherapy regimens due to its adverse neurological side effects when administered at an effective dose (5). Unfortunately, physicians are increasingly being forced to use drugs like DCS to combat antibiotic-resistant bacterial infections. The development of new drugs is in high demand. The continued characterization of drugs like DCS could play a pivotal role in the development of novel drugs. The identification of additional DCS targets and the characterization of additional DCS resistance mechanisms could contribute to the development of new drugs with novel targets that possess less adverse effects.The Escherichia coli cycA gene codes for a permease that transports the antibiotic D-cycloserine and the amino acids ␤-/L-/Dalanine, glycine, and D-serine when grown in minimal glucose or glycerol media (6-10). A mutation in the cycA gene in the E. coli K-12 and the uropathogenic E. coli (UPEC) CFT073 strains results in increased DCS resistance when grown in a minimal medium (6,11,12). The resistance to and transport of DCS in a complex medium, like Luria Bertani (LB), or a biologically relevant medium, such as human urine, has not been reported for E. coli. As a result, the role cycA ...

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Section: Discussionmentioning

confidence: 99%

Characterization of Escherichia coli d -Cycloserine Transport and Resistant Mutants

2013

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“…Several D-AAs were detected in foodstuffs (e.g., yogurt and other fermented foods) and/or biological samples (e.g., plasma). 71 The use of DBDPyNCS enantiomers (R and S forms) seems to provide significantly advanced analyses in the field of D-AAs.…”

Section: Reagents For Chiral Amines and Carboxylic Acidsmentioning

confidence: 99%

Derivatization-based High-throughput Bioanalysis by LC-MS

Toyo’oka

2017

ANAL. SCI.

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Liquid chromatography coupled with mass spectrometry (LC-MS) is one of the most prominent analytical techniques due to its inherent selectivity and sensitivity. LC-MS is currently the first choice for high-throughput bioanalysis due to the advancements in MS instruments and the analytical software. Based on this situation, we are developing various types of derivatization reagents, including chiral reagents for MS and/or MS/MS detection. These developed reagents are adopted for the detection of biomarker candidates related to diseases. The biomarker candidates include not only achiral molecules, but also chiral ones. Although determining the already-identified chiral molecules is relative easy, it is very difficult to identify and/or determine unknown enantiomer(s) in real samples. To solve this difficulty, we proposed a new strategy to identify unknown enantiomeric biomarkers related to diseases. This review paper deals with the development of derivatization reagents for amines and carboxylic acids in LC-MS analysis and their application to bioanalysis.

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“…The absolute configuration of alanine was determined by LC-MS as a fluorescence-labelled chiral derivative, as described previously. 23) NMR spectroscopy. NMR spectra of O-antigen polysaccharide and core oligosaccharide were recorded on Bruker Avance 400 and 800 spectrometers (Bruker Biospin, Karlsruhe, Germany) in D 2 O with acetone as internal standard ( H 2.225 and C 31.45).…”

Section: ) D-rham-mentioning

confidence: 99%

“…Detached soybean leaves (three for each strain) were soaked in bacterial suspension for 20 min or sprayed with the suspension. The inoculated leaves were incubated under 85% humidity in a growth cabinet for 10-14 d at 23 C under an 18-h photoperiod. To maintain turgidity, the detached leaves were watered to the cut petiole.…”

Section: )mentioning

confidence: 99%

Defects inD-Rhamnosyl Residue Biosynthetic Genes Affect Lipopolysaccharide Structure, Motility, and Cell-Surface Hydrophobicity inPseudomonas syringaePathovarglycineaRace 4

Chiku

Tsunemi

Yamamoto

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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Determination ofd-Amino Acids Labeled with Fluorescent Chiral Reagents,R(−)- andS(+)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7- (N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazoles, in Biological and Food Samples by Liquid Chromatography

Cited by 76 publications

References 31 publications

Characterization of Escherichia coli d -Cycloserine Transport and Resistant Mutants

Characterization of Escherichia coli d -Cycloserine Transport and Resistant Mutants

Derivatization-based High-throughput Bioanalysis by LC-MS

Defects inD-Rhamnosyl Residue Biosynthetic Genes Affect Lipopolysaccharide Structure, Motility, and Cell-Surface Hydrophobicity inPseudomonas syringaePathovarglycineaRace 4

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