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Are α-Oxoaldehydes Precursors for Pentosidine formation? A Comparative DFT Study.
MedLine Citation:
PMID:  22335775     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
We report a comprehensive density functional theory (DFT) study of the mechanism of pentosidine formation. This work is a continuation of our earlier studies in which we proposed pathways for formation of glucosepane (Journal of Molecular Modeling, 2011; online published; DOI 10.1007/s00894-011-1161-x), GODIC (glyoxal-derived imidazolium cross-link) and MODIC (methyl glyoxal-derived imidazolium cross-link) (Journal of Physical Chemistry, 2011; online published; DOI: 10.1021/jp205558d). Here we show that formation of pentosidine via reaction of α-oxoaldehydes with lysine and arginine in aqueous solution is possible thermodynamically and kinetically, in good agreement with the available experimental evidence. Five pathways, A-E, were characterized, as in our previous GODIC and MODIC work. In pathways A and B, a Schiff base is first formed from lysine and methyl glyoxal (MGO), and this is followed by addition of arginine and glyoxal (GO). By contrast, in pathways C, D and E, addition of arginine to MGO occurs first, resulting in formation of imidazolone, which then reacts with lysine and GO to give pentosidine. Our calculations show that the reaction process is highly exothermic, and that the three pathways, A, C and E, are competitive. These results serve to underline the potentially important role that α-oxoaldehydes play as precursors in pentosidine formation in the complex field of glycation.
Authors:
Rasoul Nasiri; Martin J Field; Mansour Zahedi
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-2-15
Journal Detail:
Title:  The journal of physical chemistry. A     Volume:  -     ISSN:  1520-5215     ISO Abbreviation:  -     Publication Date:  2012 Feb 
Date Detail:
Created Date:  2012-2-16     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9890903     Medline TA:  J Phys Chem A     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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