1999
DOI: 10.1021/jf990237i
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Convenient Synthesis of Lactuloselysine and Its Use for LC-MS Analysis in Milk-like Model Systems

Abstract: The synthesis of the Amadori product lactuloselysine [N(epsilon)-(1-deoxy-D-lactulosyl-1)-L-lysine] was obtained starting from FMOC-lysine-OH (N(alpha)-9-fluorenylmethoxy-carbonyl-N(epsilon)H(2)-L-lysine-OH) and lactose. Compound identity was confirmed by MALDI-ToF, electrospray, and NMR analysis. A selective LC-MS procedure which allowed the detection of lactuloselysine up to 10 ng mL(-)(1) was set up and used to follow the formation of the compound in a lactose-lysine model system; quantification of this mol… Show more

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Cited by 13 publications
(8 citation statements)
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“…Detection of lactulosyllysine has been conducted by spectroscopy techniques such as MALDI-TOF, electrospray and nuclear magnetic resonance (NMR) analysis. A selective liquid chromatography (LC)-MS procedure allowed the detection and quantification of lactulosyllysine after complete enzymatic hydrolysis in milk samples [48]. One of the main problems related to the direct quantification of lactulosyl-lysine and other Amadori compounds is the lack of a pure standard [35,49].…”
Section: Direct Analysis Of Amadori Compoundsmentioning
confidence: 99%
“…Detection of lactulosyllysine has been conducted by spectroscopy techniques such as MALDI-TOF, electrospray and nuclear magnetic resonance (NMR) analysis. A selective liquid chromatography (LC)-MS procedure allowed the detection and quantification of lactulosyllysine after complete enzymatic hydrolysis in milk samples [48]. One of the main problems related to the direct quantification of lactulosyl-lysine and other Amadori compounds is the lack of a pure standard [35,49].…”
Section: Direct Analysis Of Amadori Compoundsmentioning
confidence: 99%
“…A HPLC‐MS quantification of lactuloselysine in milk‐like model system using synthetic N ‐(1‐deoxy‐ d ‐lactulosyl‐1)‐ l ‐lysine‐OH as standard is set up to monitor the blockage of lysine residues during milk processing (Vinale, Monti, Panunzi, & Fogliano, ). While most of these methods are suitable for single AC or ACs in single kind of food material (Katayama et al., ).…”
Section: Introductionmentioning
confidence: 99%
“…Initially, early products are formed, such as lactosyllysine and the Amadori product, lactulosyllysine. The latter can be measured in heated milk after enzymatic degradation by ion-exchange chromatography [1] or HPLC/MS [2]. Using an antibody specific for lactosylated proteins, the Amadori product can also be detected in processed milk without hydrolysis step by enzymelinked immunosorbent assay (ELISA) or immunoblotting [3,4].…”
Section: Introductionmentioning
confidence: 99%