A Fundamental Study of Amadori Rearrangement Products in Reducing Sugar-Amino Acid Model System by Electrospray Ionization Mass Spectrometry and Computation

Y.F. Zhang; E.D. Ruan; H. Wang; Y.Y. Ruan; G.J. Shao; J.L. Aalhus; M. Juarez

doi:10.14233/ajchem.2014.16078

Issue

Vol. 26 No. 10 (2014): Vol 26 Issue 10

Issue Published : May 10, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

A Fundamental Study of Amadori Rearrangement Products in Reducing Sugar-Amino Acid Model System by Electrospray Ionization Mass Spectrometry and Computation

https://doi.org/10.14233/ajchem.2014.16078

Y.F. Zhang

Hebei Key Laboratory of Applied Chemistry, College of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao 066004, P.R. China ; These authors have equal contribution

E.D. Ruan

Agriculture and Agri-Food Canada, 6000 C&E Trail, Lacombe Research Centre, Alberta, T4L 1W1, Canada ;These authors have equal contribution

H. Wang

Agriculture and Agri-Food Canada, 6000 C&E Trail, Lacombe Research Centre, Alberta, T4L 1W1, Canada

Y.Y. Ruan

Department of Bioengineering, Jilin Agriculture Science and Technology College, Jilin 132101, P.R. China

G.J. Shao

Hebei Key Laboratory of Applied Chemistry, College of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao 066004, P.R. China

J.L. Aalhus

Agriculture and Agri-Food Canada, 6000 C&E Trail, Lacombe Research Centre, Alberta, T4L 1W1, Canada

M. Juarez

Agriculture and Agri-Food Canada, 6000 C&E Trail, Lacombe Research Centre, Alberta, T4L 1W1, Canada

Corresponding Author(s) : E.D. Ruan

Eric.Ruan@Agr.gc.ca; shaogj@ysu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 10 (2014): Vol 26 Issue 10
Article Published : May 10, 2014

Abstract

It is crucial to characterize Amadori rearrangement products (ARPs) formed in the early stage of Maillard reaction, one of the most important modifications in food science. We setup a reaction model system using six selected amino acids (arginine, asparagines, glutamine, histamine, lysine and tryptophan) and their N-terminal acetylated forms with different reducing sugars for a fundamental study of Amadori rearrangement products. The effects on forming Amadori rearrangement products were studied by using electrospray ionization mass spectrometry (ESI-MS). The reaction rate was affected by reaction temperature, reaction time, property of sugars and amino acids and the fragmentation mechanism of Amadori rearrangement products was illustrated by tandem MS (MS²) with collision-induced dissociation. The proposed fragmentation mechanism of Amadori rearrangement products in MS² was provided based on MS² data and it was supported by their computational data of density functional theory (DFT) at the B3LYP/6-31++G(d,p) level.

Keywords

Amadori rearrangement products Maillard reaction ESI-MS Density functional theory Fragmentation

Zhang, Y., Ruan, E., Wang, H., Ruan, Y., Shao, G., Aalhus, J., & Juarez, M. (2014). A Fundamental Study of Amadori Rearrangement Products in Reducing Sugar-Amino Acid Model System by Electrospray Ionization Mass Spectrometry and Computation. Asian Journal of Chemistry, 26(10), 2941–2944. https://doi.org/10.14233/ajchem.2014.16078

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References

L.C. Maillard, C.R. Acad. Sci. Ser. 2, 154, 66 (1912).
L.C. Maillard, C.R. Seances Soc. Biol. Paris, 72, 599 (1912).
J.E. Hodge, J. Agric. Food Chem., 1, 928 (1953); doi:10.1021/jf60015a004.
J.E. Hodge and C.E. Rist, J. Am. Chem. Soc., 75, 316 (1953); doi:10.1021/ja01098a019.
A. Abrams, P.H. Lowy and H. Borsook, J. Am. Chem. Soc., 77, 4794 (1955); doi:10.1021/ja01623a030.
T. Davidek, F. Robert, S. Devaud, F.A. Vera and I. Blank, J. Agric. Food Chem., 54, 6677 (2006); doi:10.1021/jf060668i.
M. Roscic, C. Versluis, A.J. Kleinnijenhuis, S. Horvat and A.J. Heck, Rapid Commun. Mass Spectrom., 15, 1002 (2001); doi:10.1002/rcm.334.
P.J. Thornalley, Ann. N. Y. Acad. Sci., 1043, 111 (2005); doi:10.1196/annals.1333.014.
M.C. Thomas, J.W. Baynes, S.R. Thorpe and M.E. Cooper, Curr. Drug Targets, 6, 453 (2005); doi:10.2174/1389450054021873.
O. Novotny, K. Cejpek and J. Velisek, Czech. J. Food Sci., 25, 119 (2007).
F. Robert, F.A. Vera, F. Kervella, T. Davidek and I. Blank, Ann. N. Y. Acad. Sci., 1043, 63 (2005); doi:10.1196/annals.1333.008.
A. Frolov, P. Hoffmann and R. Hoffmann, J. Mass Spectrom., 41, 1459 (2006); doi:10.1002/jms.1117.
L.B. Fay and H. Brevard, Mass Spectrom. Rev., 24, 487 (2005); doi:10.1002/mas.20028.
T. Yalcin and A.G. Harrison, J. Mass Spectrom., 31, 1237 (1996); doi:10.1002/(SICI)1096-9888(199611)31:11<1237::AID-JMS416>3.0.CO;2-P.
A.D. Becke, Chem. Phys., 98, 5648 (1993); doi:10.1063/1.464913.
T. Clark, J. Chandrasekhar, G.W. Spitznagel and P.R. Schleyer, J. Comput. Chem., 4, 294 (1983); doi:10.1002/jcc.540040303.
V.F. Taylor, R.E. March, H.P. Longerich and C.J. Stadey, Int. J. Mass Spectrom., 243, 71 (2005); doi:10.1016/j.ijms.2005.01.001.
S. Horvat and A. Jakas, J. Pept. Sci., 10, 119 (2004); doi:10.1002/psc.519.
A. Jakas, A. Katic, N. Bionda and S. Horvat, Carbohydr. Res., 343, 2475 (2008); doi:10.1016/j.carres.2008.07.003.
I. Jeric, C. Versluis, S. Horvat and A.J.R. Heck, J. Mass Spectrom., 37, 803 (2002); doi:10.1002/jms.337.

References

L.C. Maillard, C.R. Acad. Sci. Ser. 2, 154, 66 (1912).

L.C. Maillard, C.R. Seances Soc. Biol. Paris, 72, 599 (1912).

J.E. Hodge, J. Agric. Food Chem., 1, 928 (1953); doi:10.1021/jf60015a004.

J.E. Hodge and C.E. Rist, J. Am. Chem. Soc., 75, 316 (1953); doi:10.1021/ja01098a019.

A. Abrams, P.H. Lowy and H. Borsook, J. Am. Chem. Soc., 77, 4794 (1955); doi:10.1021/ja01623a030.

T. Davidek, F. Robert, S. Devaud, F.A. Vera and I. Blank, J. Agric. Food Chem., 54, 6677 (2006); doi:10.1021/jf060668i.

M. Roscic, C. Versluis, A.J. Kleinnijenhuis, S. Horvat and A.J. Heck, Rapid Commun. Mass Spectrom., 15, 1002 (2001); doi:10.1002/rcm.334.

P.J. Thornalley, Ann. N. Y. Acad. Sci., 1043, 111 (2005); doi:10.1196/annals.1333.014.

M.C. Thomas, J.W. Baynes, S.R. Thorpe and M.E. Cooper, Curr. Drug Targets, 6, 453 (2005); doi:10.2174/1389450054021873.

O. Novotny, K. Cejpek and J. Velisek, Czech. J. Food Sci., 25, 119 (2007).

F. Robert, F.A. Vera, F. Kervella, T. Davidek and I. Blank, Ann. N. Y. Acad. Sci., 1043, 63 (2005); doi:10.1196/annals.1333.008.

A. Frolov, P. Hoffmann and R. Hoffmann, J. Mass Spectrom., 41, 1459 (2006); doi:10.1002/jms.1117.

L.B. Fay and H. Brevard, Mass Spectrom. Rev., 24, 487 (2005); doi:10.1002/mas.20028.

T. Yalcin and A.G. Harrison, J. Mass Spectrom., 31, 1237 (1996); doi:10.1002/(SICI)1096-9888(199611)31:11<1237::AID-JMS416>3.0.CO;2-P.

A.D. Becke, Chem. Phys., 98, 5648 (1993); doi:10.1063/1.464913.

T. Clark, J. Chandrasekhar, G.W. Spitznagel and P.R. Schleyer, J. Comput. Chem., 4, 294 (1983); doi:10.1002/jcc.540040303.

V.F. Taylor, R.E. March, H.P. Longerich and C.J. Stadey, Int. J. Mass Spectrom., 243, 71 (2005); doi:10.1016/j.ijms.2005.01.001.

S. Horvat and A. Jakas, J. Pept. Sci., 10, 119 (2004); doi:10.1002/psc.519.

A. Jakas, A. Katic, N. Bionda and S. Horvat, Carbohydr. Res., 343, 2475 (2008); doi:10.1016/j.carres.2008.07.003.

I. Jeric, C. Versluis, S. Horvat and A.J.R. Heck, J. Mass Spectrom., 37, 803 (2002); doi:10.1002/jms.337.

Issue

Vol. 26 No. 10 (2014): Vol 26 Issue 10

A Fundamental Study of Amadori Rearrangement Products in Reducing Sugar-Amino Acid Model System by Electrospray Ionization Mass Spectrometry and Computation

Corresponding Author(s) : E.D. Ruan

Abstract

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