95464-27-0Relevant articles and documents
Transport of the Advanced Glycation End Products Alanylpyrraline and Pyrralylalanine by the Human Proton-Coupled Peptide Transporter hPEPT1
Stefanie, Geissler,Michael, Hellwig,Madlen, Zwarg,Fritz, Markwardt,Thomas, Henle,Matthias, Brandsch
, p. 2543 - 2547 (2010)
The glycation compound pyrraline, which originates from the advanced Maillard reaction, appears in urine after consumption of pyrraline-containlng food. We hypothesized that the absorption of pyrraline occurs In the form of dipeptides rather than the free amino acid. The human Intestinal peptide transporter hPEPT1 was transiently expressed in HeLa cells. In hPEPT1-transfected cells but not in cells transfected with empty vector, the uptake of [14C]glycylsarcosine was strongly inhibited by alanylpyrraline (Ala-Pyrr) and pyrralylalanine (Pyrr-Ala). Free pyrraline did not inhibit peptide uptake. In Xenopus laevis oocytes expressing human PEPT1, both Ala-Pyrr and Pyrr-Ala generated significant inward directed currents. In a third approach, uptake of the dipeptides into hPEPT1 -transfected HeLa cells was analyzed by HPLC. Ala-Pyrr and Pyrr-Ala were taken up by hPEPT1-expressing cells at a 4- to 7-fold higher rate than by HeLa cells transfected with the empty vector. We conclude that pyrraline containing dipeptides are transported by hPEPT1 in an electrogenlc manner into Intestinal cells. 2010 American Chemical Sudety.
Transport of free and peptide-bound pyrraline at intestinal and renal epithelial cells
Hellwig, Michael,Geissler, Stefanie,Peto, Anett,Knuetter, Ilka,Brandsch, Matthias,Henle, Thomas
, p. 6474 - 6480 (2009)
Pyrraline is a quantitatively dominating glycation compound of the advanced Maillard reaction in foods and can be found in urine after consumption of pyrraline-containing food items. The purpose of this study was to investigate the transport of pyrraline
Synthesis of monolysyl advanced glycation endproducts and their incorporation into collagen model peptides
Woods, Tom M.,Kamalov, Meder,Harris, Paul W. R.,Cooper, Garth J. S.,Brimble, Margaret
, p. 5740 - 5743 (2013/01/15)
The synthesis of advanced glycation endproducts (AGEs), CML, CEL, and pyrraline and their incorporation into collagen model peptides is reported. AGEs are modified amino acids that form on proteins such as collagen and are thought to play a significant role in the pathogenesis of many diseases, particularly diabetes. The synthesis and incorporation of these compounds into synthetic peptides is a key step in developing model systems with which to investigate AGE-modified proteins.
Identification of new heterocyclic nitrogen compounds from glucose-lysine and xylose-lysine Maillard model systems
Bailey, Richard G.,Ames, Jennifer M.,Mann, John
, p. 6240 - 6246 (2007/10/03)
Aqueous sugar (glucose or xylose)-lysine model systems were heated at 80°C for 6 h with the pH maintained at a predetermined value (3, 4, or 5). Selected compounds were isolated by combinations of solvent extraction and semipreparative HPLC, prior to identification by NMR and mass spectrometry. Two compounds were identified from the pH 5 glucose system and were identified as ε-[2-formyl-5-(hydroxymethyl)pyrrole 1-yl]-L-norleucine (pyrraline) and the new compound, 1-(5-carboxy-5-aminopentyl)-2-formyl-3-(1,2,3-trihydroxypropyl)pyrrole. A third compound was partially characterized. 2-Acetyl-5-hydroxymethyl-5,6-dihydro-4H-pyridinone was identified in the pH 3 xylose system, and the new compound, 8-furan-2-yl-methyl-5-hydroxymethyl-5,6-dihydro-indolizine-1,7-dione, was identified in the pH 4 xylose system. 2-Furfurylidene-4-hydroxy-5-methyl-3(2H)-furanone was identified in both xylose systems. Mechanisms of formation are proposed for the novel compounds.
Formation of Aromatic Compounds from Carbohydrates. IX. Reaction of D-Glucose and L-Lysine in Slightly Acidic, Aqueous Solution
Miller, Raya,Olsson, Kjell,Pernemalm, Per-Ake
, p. 689 - 694 (2007/10/02)
The title reaction yielded 1-deoxy-1-(N6-lysino)-D-fructose, (+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine, the new 5-(3,4,5,6-tetrahydropyrid-3-ylidenemethyl)-2-furanmethanol and several compounds previously identified as products in the reaction of D-glucose with methylamine or glycine under similar conditions.The lysine slowly racemized during the reaction.Such racemization of amino acids might contribute to the nutritional loss caused by Maillard reactions in food.
