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The role of dicarbonyl compounds in non-enzymatic crosslinking: a structure-activity study.

Abstract：

:The Maillard reaction is a complex network of reactions that has been shown to result in the non-enzymatic crosslinking of proteins. Recent attention has focussed on the role of alpha-dicarbonyl compounds as important in vivo contributors to protein crosslinking but, despite extensive research, the molecular mechanisms of the crosslinking reaction remain open to conjecture. In particular, no relationship between the structure of the carbonyl-containing compounds and their activity as crosslinking agents has been established. In an effort to elucidate a structure-reactivity relationship, a wide range of dicarbonyl compounds, including linear, cyclic, di-aldehyde and di-ketone compounds, were reacted with the model protein ribonuclease A and their crosslinking activity assessed. Methylglyoxal and glutaraldehyde were found to be the most efficient crosslinkers, whilst closely related molecules effected crosslinking at a much lower rate. Cyclopentan-1,2-dione was also shown to be a reactive crosslinking agent. The efficiency of methylglyoxal and glutaraldehyde at crosslinking is thought to be related to their ability to form stable heterocyclic compounds that are the basis of protein crosslinks. The reasons for the striking reactivity of these two compounds, compared to closely related structures is explained by subtle balances between competing pathways in a complex reaction network.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Meade SJ,Miller AG,Gerrard JA

doi

10.1016/s0968-0896(02)00564-3

subject

Has Abstract

pub_date

2003-03-20 00:00:00

pages

853-62

issue

6

eissn

0968-0896

issn

1464-3391

pii

S0968089602005643

journal_volume

11

pub_type

杂志文章

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