Protein fructosylation: fructose and the Maillard reaction

https://doi.org/10.1093/ajcn/58.5.779SGet rights and content

ABSTRACT

Fructose, as is the case for other reducing sugars, undergoes the Maillard reaction with proteins and amino acids. The first stage of the reaction results in one or more substituted amino sugars. These products in turn enter the advanced and final stages of the Maillard reaction, which involve the formation of reactive intermediates, cross-linking of proteins, and the formation of brown and fluorescent polymeric materials. It would appear that the initial stages of the reaction occur more rapidly with fructose than with glucose. The Maillard reaction with any sugar, including fructose, results in a decrease in protein quality due to the loss of amino acid residues and decreased protein digestibility. Maillard products can inhibit the uptake and metabolism of free amino acids and of other nutrients such as zinc and some advanced Maillard products have mutagenic and/ or anticarcinogenic properties. In vivo the Maillard reactions between proteins and fructose, glucose, and other reducing sugars may play a role in aging and in some of the clinical complications of diabetes.

References (120)

  • OimomiM et al.

    Fructose-related glycation

    Diabetes Res Clin Pract

    (1989)
  • RazaK et al.

    Non-enzymic modification of lens proteins by glucose and fructose: effects of ibuprofen

    Exp Eye Res

    (1991)
  • DanehyJP

    Maillard reactions: nonenzymatic browning in food systems with special reference to the development of flavor

    Adv Food Res

    (1986)
  • KatoH et al.

    Metabolism of 3-deoxyglucosone, an intermediate compound in the Maillard reaction, administered orally or intravenously to rats

    Biochim Biophys Acta

    (1990)
  • KnechtKJ et al.

    Detection of 3-deoxyfructose and 3-deoxyglucosone in human urine and plasma: evidence for intermediate stages of the Maillard reaction in vivo

    Arch Biochem Biophys

    (1992)
  • DillsWL

    3-Deoxy-D-ezyr/iro-hexulose: a convenient synthesis and its interaction with the enzymes of fructose metabolism

    Carbohydr Res

    (1990)
  • YenGC et al.

    Antimutagenic effect of Maillard browning products obtained from amino acids and sugars

    Food Chem Toxicol

    (1992)
  • MacGregorJT et al.

    Non-clastogenicity in mouse bone marrow of fructose/lysine and other sugar/amino acid browning products with in vitro genotoxicity

    Food Chem Toxicol

    (1989)
  • ChanRIM et al.

    Antimutagenic activity of browning reaction products

    Cancer Lett

    (1982)
  • PoulsomR et al.

    The effects of long-term treatment of streptozotocin-diabetic rats with an aldose reductase inhibitor

    Exp Eye Res

    (1983)
  • MayesPA

    Intermediary metabolism of fructose.

    Am J Clin Nutr

    (1993)
  • BaynesJW et al.

    The Maillard reaction in aging, diabetes, and nutrition.

    (1989)
  • FinotPA et al.

    The Maillard reaction.

    Advances in life sciences.

    (1990)
  • HodgeJE

    Chemistry of browning reactions in model systems

    J Agric Food Chem

    (1953)
  • MauronJ

    The Maillard reaction in food: a critical review from the nutritional standpoint

    Prog Food Sci

    (1981)
  • CeramiA

    Hypothesis, glucose as a mediator of aging

    J Am Geriatr Soc

    (1985)
  • MonnierVM et al.

    Mechanisms of protection against damage mediated by the Maillard reactions of aging

    Geronotology

    (1991)
  • KaananeA et al.

    The Maillard reaction in foods.

  • OsteR

    Effect of Maillard reaction products on protein digestion.

  • FinotPA et al.

    Metabolic transit and toxicity of Maillard reaction products.

  • HurrellRF

    Influence of the Maillard reaction on the nutritional value of foods.

  • FinotPA

    Metabolism and physiological effects of Maillard reaction products (MRP).

  • MonnierVM

    Toward a Maillard theory of aging.

  • MonnierVM et al.

    The Maillard reaction as a basis for the theory of aging.

  • LedlF et al.

    Chemical pathways of the Maillard reaction.

  • NjorogeFG et al.

    The chemistry of the Maillard reaction under physiological conditions: a review.

  • LedlF

    Chemical pathways of the Maillard reaction.

  • KatoY et al.

    Maillard reaction in sugar protein systems.

  • HeynsK et al.

    About the formation of 2-aminoaldoses during the decomposition of ketosylamines (Uber die Gewinnung von 2-Amino-aldosen durch Umlagerung von Ketosylaminen).

    Chem Ber

    (1957)
  • IsbelHS et al.

    Mutarotation, hydrolysis, and rearrangement reactions of glycosylamines

    J Org Chem

    (1958)
  • HeynsK et al.

    Formation of N-Substituted-2-amino-2-deoxy-glucoses during the reaction of fructose with peptides (N-Substi-tuierte 2-Amino-2-deoxy-D-glucosen durch Umsetzung von D-Fructose mit Peptiden).

    Chem Ber

    (1959 50)
  • HeynsK et al.

    The reaction of fructose with gelatin (Die Umsetzung von D-Fructose mit Gelatine).

    Chem Ber

    (1959)
  • HeynsK et al.

    The reaction of fructose with L-Lysine and L-Arginine and its relationship to the nonenzymatic browning reactions (Die Umsetzung von D-Fructose mit L-Lysin und L-Argigni und deren Bezeihung zu nichtenzymatischen Braunungsreak-tionen).

    Chem Ber

    (1962)
  • HeynsK et al.

    The reaction of L-Tryptophan and L-Histidine with hexoses (Die Umsetzung von L-Tryptophan und L-Histidin mit Hexosen).

    Chem Ber

    (1964)
  • McPhersonJD et al.

    Role of fructose in glycation and cross-linking of proteins

    Biochemistry

    (1988)
  • SuarezG

    Nonenzymatic browning of proteins and the sorbitol pathway.

  • KatoH et al.

    3-Deoxygluco-sone, an intermediate product of the Maillard reaction.

  • IgakiN et al.

    The role of 3-deoxyglucosone in the Maillard reaction.

  • ShinDB et al.

    Polymerization of proteins caused by reaction with sugars and the formation of 3-deoxyglucosone under physiological conditions

    Agric Biol Chem

    (1988)
  • ImasatoH et al.

    Maillard reaction VI: structural determinations in melanoidins from fructose and glycine

    An Acad Bras Cienc

    (1981)
  • Cited by (0)

    View full text