159
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Autoxidation of ascorbate mediates lysine N-pyrrolation

, , &
Pages 749-759 | Received 05 Sep 2022, Accepted 26 Jan 2023, Published online: 07 Feb 2023

References

  • Golumbic C, Mattill HA. Antioxidants and the autoxidation of fats. XIII. The antioxygenic action of ascorbic acid in association with tocopherols, hydroquinones and related compounds. J Am Chem Soc. 1941;63(5):1279–1280.
  • Burton GW, Ingold KU. Vitamin E: application of the principles of physical organic chemistry to the exploration of its structure and function. Acc Chem Res. 1986;19(7):194–201.
  • Levine M, Morita K. Ascorbic acid in endocrine systems. Vitam Horm. 1985;42:1–64.
  • Nemet I, Monnier VM. Vitamin C degradation products and pathways in the human lens. J Biol Chem. 2011;286(43):37128–37136.
  • Dunn JA, Ahmed MU, Murtiashaw MH, et al. Reaction of ascorbate with lysine and protein under autoxidizing conditions: formation of Nε-(carboxymethyl)lysine by reaction between lysine and products of autoxidation of ascorbate. Biochemistry. 1990;29(49):10964–10970.
  • Nagaraj RH, Sell DR, Prabhakaram M, et al. High correlation between pentosidine protein crosslinks and pigmentation implicates ascorbate oxidation in human lens senescence and cataractogenesis. Proc Natl Acad Sci USA. 1991;88(22):10257–10261.
  • Tessier F, Obrenovich M, Monnier VM. Structure and mechanism of formation of human lens fluorophore LM-1. Relationship to vesperlysine A and the advanced Maillard reaction in aging, diabetes, and cataractogenesis. J Biol Chem. 1999;274(30):20796–20804.
  • Brownlee M, Cerami A, Vlassara H. Advanced glycosylation end products in tissue and the biochemical basis of diabetic complications. N Engl J Med. 1988;318(20):1315–1321.
  • Baynes JW, Monnier VM. The Maillard reaction in aging, diabetes and nutrition. Proceedings of an NIH Conference. Bethesda, MD, September 22–23, 1988. Dedicated to John E. Hodge on the occasion of his 75th birthday. Prog Clin Biol Res. 1989;304:1–410.
  • Miyashita H, Chikazawa M, Otaki N, et al. Lysine pyrrolation is a naturally-occurring covalent modification involved in the production of DNA mimic proteins. Sci Rep. 2014;4:5343.
  • Chikazawa M, Yoshitake J, Lim SY, et al. Glycolaldehyde is an endogenous source of lysine N-pyrrolation. J Biol Chem. 2020;295(22):7697–7709.
  • Buettner GR. In the absence of catalytic metals ascorbate does not autoxidize at pH 7: ascorbate as a test for catalytic metals. J Biochem Biophys Methods. 1988;16(1):27–40.
  • Sutton HC, Winterbourn CC. Chelated iron-catalyzed OH. formation from paraquat radicals and H2O2: mechanism of formate oxidation. Arch Biochem Biophys. 1984;235(1):106–115.
  • Shen J, Griffiths PT, Campbell SJ, et al. Ascorbate oxidation by iron, copper and reactive oxygen species: review, model development, and derivation of key rate constants. Sci Rep. 2021;11(1):7417.
  • Qian SY, Buettner GR. Iron and dioxygen chemistry is an important route to initiation of biological free radical oxidations: an electron paramagnetic resonance spin trapping study. Free Radic Biol Med. 1999;26(11–12):1447–1456.
  • Thornalley P, Wolff S, Crabbe J, et al. The autoxidation of glyceraldehyde and other simple monosaccharides under physiological conditions catalysed by buffer ions. Biochim Biophys Acta. 1984;797(2):276–287.
  • Onyango AN. Small reactive carbonyl compounds as tissue lipid oxidation products; and the mechanisms of their formation thereby. Chem Phys Lipids. 2012;165(7):777–786.
  • Greven WL, Waanders F, Nagai R, et al. Mesangial accumulation of GA-pyridine, a novel glycolaldehyde-derived AGE, in human renal disease. Kidney Int. 2005;68(2):595–602.
  • Nagai R, Hayashi CM, Xia L, et al. Identification in human atherosclerotic lesions of GA-pyridine, a novel structure derived from glycolaldehyde-modified proteins. J Biol Chem. 2002;277(50):48905–48912.
  • Acharya AS, Manning JM. Reaction of glycolaldehyde with proteins: latent crosslinking potential of alpha-hydroxyaldehydes. Proc Natl Acad Sci U S A. 1983;80(12):3590–3594.
  • Argirov OK, Lin B, Olesen P, et al. Isolation and characterization of a new advanced glycation endproduct of dehydroascorbic acid and lysine. Biochim Biophys Acta. 2003;1620(1–3):235–244.
  • Fu MX, Requena JR, Jenkins AJ, et al. The advanced glycation end product, Nε-(carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions. J Biol Chem. 1996;271(17):9982–9986.
  • Reddy S, Bichler J, Wells-Knecht KJ, et al. Nε-(carboxymethyl)lysine is a dominant advanced glycation end product (AGE) antigen in tissue proteins. Biochemistry. 1995;34(34):10872–10878.
  • Dixon SJ, Lemberg KM, Lamprecht MR, et al. Ferroptosis: an iron-dependent form of nonapoptotic cell death. Cell. 2012;149(5):1060–1072.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.