Pyrraline-d4

Chemical name: (2S)-2-amino-6-(formyl-5-hydroxymethyl-pyrrol-1-yl)-(4,4,5,5-tetradeutero)hexanoic acid // Synonyms: epsilon-Pyrrole-[4,4,5,5-D4]-L-lysine, epsilon-pyrrolyl-(4,4,5,5-tetradeutero)-lysine

Product code:HAA3045
CAS No.:2446534-02-5
Formula:C12H14D4N2O4
Molecular weight:258,31 g/mol
Grouped product items
Qty Packing unit Price SKU
5 mg
$715.50
HAA3045.0005
10 mg
$1,282.50
HAA3045.0010
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description
Maillard reaction product (MRP) are indicators for heat treatment of food and biomarkers. Pyrraline can also be called an Advanced Glycation End product (AGE), derived from reaction of glucose with lysine residues. This is the D4-isotope labelled derivative to the unlabeled compound HAA3040.

references
Formation of -(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: 1201-1 202. 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-flssigkeitschromatographischer 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. Schssler 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 raction de Maillard sur la digestion des protines. Etude sur des composs purifis; 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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