Pyrraline

Chemical name: (2S)-2-amino-6-(formyl-5-hydroxymethyl-pyrrol-1-yl)-hexanoic acid // Synonyms: epsilon-Pyrrole-L-lysine

Product code:HAA3040
CAS No.:74509-14-1
Formula:C12H18N2O4
Molecular weight:254,28 g/mol
Grouped product items
Qty Packing unit Price SKU
5 mg
$290.25
HAA3040.0005
10 mg
$459.00
HAA3040.0010
Safety Data Sheets
New
description

Maillard Reaction Products (MRPs) are indicators for the heat treatment of food, as well as markers of nutritional quality. They also appear naturally in the human body as so-called Advanced Glycation End Products (AGEs). As such, they are indicators for body health and disease processes, including inflammation, diabetes, cancer and ageing. Consequently, AGEs gained broad attention in cosmetics, biochemistry, food, and pharmaceutical applications.

This material is supplied as a salt containing varying contents of the acid counterion. The net content of each batch is specified in the respective certificate of analysis.


references

Formation of ε-(2-Formyl-5-hydroxy-methyl-pyrrol-1-yl)-l-norleucine in the Maillard Reaction betweend-Glucose andl-Lysine; T. Nakayama, F. Hayase and H. Kato; Agricultural and Biological Chemistry 2014; 44: 1201-1202. https://doi.org/10.1080/00021369.1980.10864104

Transport of free and peptide-bound pyrraline at intestinal and renal epithelial cells; M. Hellwig, S. Geissler, A. Peto, I. Knutter, M. Brandsch and T. Henle; J Agric Food Chem 2009; 57: 6474-80. https://doi.org/10.1021/jf901224p

Synthesis of pyrraline reference material; T. Henle and A. Bachmann; Z Lebensm Unters Forsch 1996; 202: 72-4. https://doi.org/10.1007/BF01229689

Pyrraline ether crosslinks as a basis for protein crosslinking by the advanced Maillard reaction in aging and diabetes; R. H. Nagaraj, M. Portero-Otin and V. M. Monnier; Archives of biochemistry and biophysics 1996; 325: 152-8. https://doi.org/10.1006/abbi.1996.0019

First evidence for accumulation of protein-bound and protein-free pyrraline in human uremic plasma by mass spectrometry; H. Odani, T. Shinzato, Y. Matsumoto, I. Takai, S. Nakai, M. Miwa, N. Iwayama, I. Amano and K. Maeda; Biochemical and biophysical research communications 1996; 224: 237-41. https://doi.org/10.1006/bbrc.1996.1013

Chromatographic evidence for pyrraline formation during protein glycation in vitro and in vivo; M. Portero-Otin, R. H. Nagaraj and V. M. Monnier; Biochim Biophys Acta 1995; 1247: 74-80. https://doi.org/10.1016/0167-4838(94)00209-y

Determination of protein-bound 2-amino-6-(2-formyl-1-pyrrolyl)-hexanoic acid (“pyrraline”) by ion exchange Chromatography and photodiode array detection; T. Henle and H. Klostermeyer; Zeitschrift fr Lebensmittel-Untersuchung und -Forschung 1993; 196: 1-4. https://doi.org/10.1007/bf01192975

Maillard-reaktion von rinderserumalbumin mit glucose hochleistung-flüssigkeitschromatographischer nachweis des 2-formyl-5-(hydroxymethyl)pyrrol-1-norleucins nach alkalischer hydrolyse; M. Sengl, F. Ledl and T. Severin; Journal of Chromatography A 1989; 463: 119-125. https://doi.org/10.1016/s0021-9673(01)84458-7

[Maillard reaction of bovine serum albumin with glucose. Determination of 2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine by high-performance liquid chromatography after alkaline hydrolysis]; M. Sengl, F. Ledl and T. Severin; J Chromatogr 1989; 463: 119-25. https://doi.org/10.1016/s0021-9673(01)84458-7

Direct determination of 2-amino-6-(2-formyl-5-hydroxymethyl-l-pyrrolyl)-hexanoic acid in hydrolyzed protein by reversed-phase HPLC; U. Schüssler and F. Ledl; Zeitschrift fr Lebensmittel-Untersuchung und -Forschung 1989; 189: 32-35. https://doi.org/10.1007/bf01120444

Synthesis of 2-amino-6-(2-formyl-5-hydroxymethyl-1-pyrrolyl-)hexanoic acid; U. Schfiler and F. Ledl; Zeitschrift fr Lebensmittel-Untersuchung und -Forschung 1989; 189: 138-140. https://doi.org/10.1007/bf01332948

Aging of proteins: immunological detection of a glucose-derived pyrrole formed during maillard reaction in vivo; F. Hayase, R. H. Nagaraj, S. Miyata, F. G. Njoroge and V. M. Monnier; J Biol Chem 1989; 264: 3758-64.

High-performance liquid chromatographic determination of .epsilon.-pyrrole lysine in processed food; G. H. Chiang; Journal of Agricultural and Food Chemistry 1988; 36: 506-509. https://doi.org/10.1021/jf00081a025

Effect of Maillard reaction products on protein digestion. Studies on pure compounds; Effet des produits de la réaction de Maillard sur la digestion des protéines. Etude sur des composés purifiés; R. E. Oste, R. Miller, H. Sjostrom and O. Noren; J. agric. food chem. (Print) 1987; 35: 938-942.

Formation of aromatic compounds from carbohydrates. IX. Reaction of D-glucose and L-lysine in slightly acidic, aqueous solution; R. Miller, K. Olsson and P.-A. Pernemalm; Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry 1984; 38: 689-694.



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