Convenient synthesis of lactuloselysine and its use for LC-MS analysis in milk-like model systems

Francesco Vinale; Simona Maria Monti; Barbara Panunzi; Vincenzo Fogliano

doi:10.1021/jf990237i

Convenient synthesis of lactuloselysine and its use for LC-MS analysis in milk-like model systems

Francesco Vinale, Simona Maria Monti, Barbara Panunzi, Vincenzo Fogliano^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

10 Citations (Scopus)

Abstract

The synthesis of the Amadori product lactuloselysine [N(ε)(1-deoxy-D- lactulosyl-1)-L-lysine] was obtained starting from FMOC-lysine-OH (N(α)-9- fluorenylmethoxy-carbonyl-N(ε)H₂-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 molecule after complete enzymatic hydrolysis of whey-proteins from milk samples was also performed.

Original language	English
Pages (from-to)	4700-4706
Number of pages	7
Journal	Journal of Agricultural and Food Chemistry
Volume	47
Issue number	11
DOIs	https://doi.org/10.1021/jf990237i
Publication status	Published - Nov 1999
Externally published	Yes

Keywords

Lactuloselysine
LC-MS
Maillard reaction
Milklike model systems

Access to Document

10.1021/jf990237i

Cite this

@article{84ec212d03d3411f938603cea23e9189,

title = "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(ε)(1-deoxy-D- lactulosyl-1)-L-lysine] was obtained starting from FMOC-lysine-OH (N(α)-9- fluorenylmethoxy-carbonyl-N(ε)H2-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 molecule after complete enzymatic hydrolysis of whey-proteins from milk samples was also performed.",

keywords = "Lactuloselysine, LC-MS, Maillard reaction, Milklike model systems",

author = "Francesco Vinale and Monti, {Simona Maria} and Barbara Panunzi and Vincenzo Fogliano",

year = "1999",

month = nov,

doi = "10.1021/jf990237i",

language = "English",

volume = "47",

pages = "4700--4706",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Convenient synthesis of lactuloselysine and its use for LC-MS analysis in milk-like model systems

AU - Vinale, Francesco

AU - Monti, Simona Maria

AU - Panunzi, Barbara

AU - Fogliano, Vincenzo

PY - 1999/11

Y1 - 1999/11

N2 - The synthesis of the Amadori product lactuloselysine [N(ε)(1-deoxy-D- lactulosyl-1)-L-lysine] was obtained starting from FMOC-lysine-OH (N(α)-9- fluorenylmethoxy-carbonyl-N(ε)H2-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 molecule after complete enzymatic hydrolysis of whey-proteins from milk samples was also performed.

AB - The synthesis of the Amadori product lactuloselysine [N(ε)(1-deoxy-D- lactulosyl-1)-L-lysine] was obtained starting from FMOC-lysine-OH (N(α)-9- fluorenylmethoxy-carbonyl-N(ε)H2-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 molecule after complete enzymatic hydrolysis of whey-proteins from milk samples was also performed.

KW - Lactuloselysine

KW - LC-MS

KW - Maillard reaction

KW - Milklike model systems

U2 - 10.1021/jf990237i

DO - 10.1021/jf990237i

M3 - Article

C2 - 10552875

AN - SCOPUS:0033230062

SN - 0021-8561

VL - 47

SP - 4700

EP - 4706

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 11

ER -

Convenient synthesis of lactuloselysine and its use for LC-MS analysis in milk-like model systems

Abstract

Keywords

Access to Document

Fingerprint

Cite this