Synlett 2012(4): 531-534  
DOI: 10.1055/s-0031-1290348
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient Synthesis of N ε-(Carboxymethyl)lysine, a Key Advanced Glycation Endproduct Biomarker

Jeanette M. Andersena, Thomas Hjelmgaarda, Lars O. Dragstedb, John Nielsen*a
a Department of Basic Sciences and Environment, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark
Fax: +45(353)32398; e-Mail: jn@life.ku.dk;
b Department of Human Nutrition, University of Copenhagen, Rolighedsvej 30, 1958 Frederiksberg C, Denmark
Further Information

Publication History

Received 22 October 2011
Publication Date:
10 February 2012 (online)

Abstract

Advanced glycation endproducts (AGEs) are formed when sugars react with peptides and proteins without the help of enzymes and by thermal processing of food such as baking and frying. AGEs and especially N ε-(carboxymethyl)lysine (CML) has been used as general key biomarkers for oxidative stress and a number of diseases associated with poor lifestyle. Herein we present the first synthetic pathway to the free zwitter ion of CML via a protected intermediate.

    References

  • 1 Glomb MA. Monnier VM. J. Biol. Chem.  1995,  270:  10017 
  • 2 Fu M.-X. Requena JR. Jenkins AJ. Lyons TJ. Baynes JW. Thorpe SR. J. Biol. Chem.  1996,  271:  9982 
  • 3 Zhang Q. Ames JM. Smith RD. Baynes JW. Metz TO. J. Proteome Res.  2009,  8:  754 
  • 4 Sell DR. Monnier VM. J. Biol. Chem.  1989,  264:  21597 
  • 5 Wells-Knecht KJ. Brinkmann E. Baynes JW. J. Org. Chem.  1995,  60:  6246 
  • 6 Ahmed MU. Thorpe SR. Baynes JW. J. Biol. Chem.  1986,  261:  4889 
  • 7 Uribarri J. Cal W. Sandu O. Peppa M. Goldberg T. Vlassara H. Ann. N. Y. Acad. Sci.  2005,  1043:  461 
  • 8 Gerrard JA. Trends Food Sci. Technol.  2006,  17:  324 
  • 9 Vlassara H. Striker GE. Nat. Rev. Endocrinol.  2011,  7:  526 
  • 10 Ahmed MU. Thorpe SR. Baynes JW. J. Biol. Chem.  1986,  261:  4889 
  • 11 Delatour T. Fenaille F. Parisod V. Arce Vera F. Buetler T. Amino Acids  2006,  30:  25 
  • 12 Pashikanti S. de Alba DR. Boissonneault GA. Cervantes-Laurean D. Free Radical Biol. Med.  2010,  48:  656 
  • 13 Takanashi M. Sakurai T. Tsuchiya S. Chem. Pharm. Bull.  1992,  40:  705 
  • 14 Matsutani H. Kusumoto S. Koizumi R. Shiba T. Phytochemistry  1979,  18:  661 
  • 15 Csuk R. Stark S. Barthel A. Kluge R. Ströhl D. Synthesis  2009,  1933 
  • 16a Grunwald S. Krause R. Bruch M. Henle T. Brandsch M. Br. J. Nutr.  2006,  95:  1221 
  • 16b Hellwig M. Geissler S. Matthes R. Peto A. Silow C. Brandsch M. Henle T. ChemBioChem  2011,  12:  1270 
  • 17 De León-Rodriguez LM. Kovacs Z. Dieckmann GR. Sherry AD. Chem. Eur. J.  2004,  10:  1149 
  • 18 Bishop JE. O’Connell JF. Rapoport H. J. Org. Chem.  1991,  56:  5079 
  • 19 Messeguer J. Masip I. Montolio M. del Rio JA. Soriano E. Messeguer A. Tetrahedron  2010,  66:  2444 
  • 20 Maresca KP. Marquis JC. Hillier SM. Lu G. Femia FJ. Zimmerman CN. Eckelman WC. Joyal JL. Babich JW. Bioconjugate Chem.  2010,  21:  1032 
  • 21 Wu X. Jiang Z. Shen H.-M. Lu Y. Adv. Synth. Catal.  2007,  349:  812 
  • 22 Gruber P. Hofmann T. J. Peptide Res.  2005,  66:  111