Synthesis of Biocytin

Wolf, Donald E.; Valiant, John; Peck, Robert L.; Folkers, Karl

doi:10.1021/ja01128a039

Cited by 31 publications

(12 citation statements)

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“…CML was synthesized as described before with minor modifications. 12,15 In brief, deuterated lysine was dissolved in water and the a-amino group was protected by addition of copper (CuCO 3 ). At alkaline pH (pH > 8) 2-bromoacetic acid was added and the solution was stirred at room temperature over 5 days.…”

Section: Synthesis Of the Labelled CML As Internal Standardmentioning

confidence: 99%

Determination of N^ε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry

Gonzalez-Reche¹,

Kucharczyk²,

Musiol³

et al. 2006

Rapid Comm Mass Spectrometry

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In order to identify new biomarkers for pulmonary diseases in exhaled breath condensate (EBC) it was the aim of this study to develop an analytical method for the identification and quantification of N epsilon-(carboxymethyl)lysine (CML) in EBC. As detection by liquid chromatography with positive electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) offers the advantage of structurally related detection with the necessary specificity required for the identification of a substance, it was the method chosen for the determination of the non-volatile compound. Specific mass transitions and comparison of retention times with standards under given conditions were used for the unequivocal identification of CML in EBC of healthy subjects. Synthesis of isotopically labelled CML was performed and used as an internal standard for an accurate determination. It was possible to identify the advanced glycation end-product CML in 8 out of 10 healthy subjects. The concentration range determined in the quantifiable examined samples ranged between 35 and 110 pg/mL. EBC samples from 11 patients with different diseases such as diabetes and chronic obstructive pulmonary disease were also measured. In one patient with pneumonia a concentration of 1509 pg CML/mL EBC could be detected. This is the first time that CML has been identified and determined in EBC. The developed LC/ESI-MS/MS method could be used to address the utility of CML as a biomarker in pulmonary diseases.

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Section: Synthesis Of the Labelled CML As Internal Standardmentioning

confidence: 99%

Determination of N^ε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry

Gonzalez-Reche¹,

Kucharczyk²,

Musiol³

et al. 2006

Rapid Comm Mass Spectrometry

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“…(25), and a-N-formyl-L-lysine (26) were obtained from the corresponding carbobenzoxy derivative followed by hydrogenation. a-N-Formyl-L-ornithine was prepared as for the lysine derivative (26), except that contaminating ornithine was removed with Amberlite IRC-50; yield, 59 %.…”

Section: Methodsmentioning

confidence: 99%

On the selectivity of acylation of unprotected diamino acids

Leclerc¹,

Benoiton²

1968

Can. J. Chem.

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p-Nitrophenyl acetate and other esters except formates, will acylate the unprotected diamino acids homolysine, lysine, and ornithine, exclusively at the ω-amino group at pH 11. At lower alkaline pH's, the reaction is preferential but not selective. The reaction with diaminobutyric acid and diaminopropionic acid is not selective at any alkaline pH. ε-N-Acetyllysine can be prepared directly by the action of excess phenyl acetate on lysine at pH 11.

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“…synthesis and purification of cml, cel, and labeled analogs Synthesis of CML, CEL, and their 2 H 4 -labeled analogs was essentially as described for biocytin (20 ). Briefly, lysine (or 2 H 4 -lysine) was converted to its copper complex to protect the ␣-amino group.…”

Section: Plasma Samplesmentioning

confidence: 99%

Measurement of Nε-(Carboxymethyl)lysine and Nε-(Carboxyethyl)lysine in Human Plasma Protein by Stable-Isotope-Dilution Tandem Mass Spectrometry

Teerlink

Barto²,

Brink³

et al. 2004

Clinical Chemistry

119

104

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Results: CML and CEL were separated with baseline resolution with a total analysis time of 21 min. The lower limit of quantification was 0.02 mol/L for both compounds. Mean recoveries from plasma samples to which CML and CEL had been added were 92% for CML and 98% for CEL. Within-day CVs were <7.2% for CML and <8.2% for CEL, and between-day CVs were <8.5% for CML and <9.0% for CEL. In healthy individuals (n ‫؍‬ 10), mean (SD) plasma concentrations of CML and CEL were 2.80 (0.40) mol/L (range, 2.1-3.4 mol/L) and 0.82 (0.21) mol/L (range, 0.5-1.2 mol/L), respectively. In hemodialysis (n ‫؍‬ 17) and peritoneal dialysis (n ‫؍‬ 9) patients, plasma concentrations of CML and CEL were increased two-to threefold compared with controls, with-

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Synthesis of Biocytin

Cited by 31 publications

References 0 publications

Determination of N^ε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry

Determination of N^ε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry

On the selectivity of acylation of unprotected diamino acids

Measurement of Nε-(Carboxymethyl)lysine and Nε-(Carboxyethyl)lysine in Human Plasma Protein by Stable-Isotope-Dilution Tandem Mass Spectrometry

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Synthesis of Biocytin

Cited by 31 publications

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Determination of Nε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry

Determination of Nε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry

On the selectivity of acylation of unprotected diamino acids

Measurement of Nε-(Carboxymethyl)lysine and Nε-(Carboxyethyl)lysine in Human Plasma Protein by Stable-Isotope-Dilution Tandem Mass Spectrometry

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Determination of N^ε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry

Determination of N^ε‐(carboxymethyl)lysine in exhaled breath condensate using isotope dilution liquid chromatography/electrospray ionization tandem mass spectrometry