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Formyline, a new glycation compound from the reaction of lysine and 3-deoxypentosone

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Abstract

A previously uncharacterized glycation compound was isolated from a reaction mixture of N-α-Boc-lysine and 3-deoxypentosone by semi-preparative ion-exchange chromatography and was identified by nuclear magnetic resonance (NMR) spectroscopy as 6-(2-formyl-1-pyrrolyl)-l-norleucine (formyline). 3-Deoxypentosone and pentoses like ribose, arabinose, or xylose were identified as the predominant precursors of the new glycation compound, but formyline can also be formed from lysine and degradation products of disaccharides and glucuronic acid. The Amadori products lactuloselysine and ribuloselysine, which were synthesized by improved methods and characterized by NMR spectroscopy, were shown not to form formyline when heated in dry state without lysine added, indicating that reactions between the lysine side chain and dicarbonyl compounds are the main pathways for formyline formation rather than transformation of lysine containing Amadori products. Finally, it was shown by HPLC analysis after enzymatic digestion that peptide-bound formyline can be formed during incubation of casein and 3-deoxypentosone under conditions comparable to food processing.

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Acknowledgments

We thank Dr. Uwe Schwarzenbolz, Institute of Food Chemistry, for the acquisition of the mass spectra. We are grateful to the members of the Institute of Organic Chemistry, namely Dr. Margit Gruner and Anett Rudolph, for recording the NMR spectra and Anke Peritz for performing the elemental analyses. This work was supported by a research grant of the Deutsche Forschungsgemeinschaft (HE 2306/9-1).

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  1. Institute of Food Chemistry, Technische Universität Dresden, 01062, Dresden, Germany

    Michael Hellwig & Thomas Henle

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  1. Michael Hellwig
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  2. Thomas Henle
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Correspondence to Thomas Henle.

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Hellwig, M., Henle, T. Formyline, a new glycation compound from the reaction of lysine and 3-deoxypentosone. Eur Food Res Technol 230, 903–914 (2010). https://doi.org/10.1007/s00217-010-1237-3

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  • DOI: https://doi.org/10.1007/s00217-010-1237-3

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