Fmoc-L-Argpyrimidine(Pbf,TBMS)-OH

Chemischer Name: (S)-2-(9-Fluorenylmethyloxycarbonylamino)-5-(N-(4,6-dimethyl-5-(t-butyldimethylsilyloxy)pyrimidin-2-yl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonamido)pentanoic acid // Synonyme: Fmoc-Argpyrimidine(Pbf,TBMS)-OH,(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(N-(4,6-dimethyl-5-(t-butyldimethylsilyloxy)pyrimidin-2-yl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonamid o)pentanoicacid; related CAS: 2147738-36-9

Art-Nr.:FAA5530
CAS Nr.:2389078-23-1
Formel:C₄₅H₅₈N₄O₈SSi
Molare Masse:843,11 g/mol

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description

Maillard reaction product (MRP) are indicators for heat treatment of food. They are used as marker of the nutritional quality of food.

Argpyrimidine is a fluorescent adduct derived from methylglyoxal and arginine residues.

references

Antioxidant properties of argpyrimidine; N. Sreejayan, X. Yang, K. Palanichamy, K. Dolence and J. Ren; Eur J Pharmacol 2008; 593: 30-5. https://doi.org/10.1016/j.ejphar.2008.07.030

Argpyrimidine, a methylglyoxal-derived advanced glycation end-product in familial amyloidotic polyneuropathy; R. Gomes, M. Sousa Silva, A. Quintas, C. Cordeiro, A. Freire, P. Pereira, A. Martins, E. Monteiro, E. Barroso and A. Ponces Freire; The Biochemical journal 2005; 385: 339-45. https://doi.org/10.1042/BJ20040833

Therapeutic potential of breakers of advanced glycation end product-protein crosslinks; S. Vasan, P. Foiles and H. Founds; Archives of biochemistry and biophysics 2003; 419: 89-96. https://doi.org/10.1016/j.abb.2003.08.016

N(delta)-(5-hydroxy-4,6-dimethylpyrimidine-2-yl)-l-ornithine, a novel methylglyoxal-arginine modification in beer; M. A. Glomb, D. Rosch and R. H. Nagaraj; J Agric Food Chem 2001; 49: 366-72. https://doi.org/10.1021/jf000493r

Argpyrimidine, a blue fluorophore in human lens proteins: high levels in brunescent cataractous lenses; P. S. Padayatti, A. S. Ng, K. Uchida, M. A. Glomb and R. H. Nagaraj; Invest Ophthalmol Vis Sci 2001; 42: 1299-304.

Methylglyoxal modification of protein. Chemical and immunochemical characterization of methylglyoxal-arginine adducts; T. Oya, N. Hattori, Y. Mizuno, S. Miyata, S. Maeda, T. Osawa and K. Uchida; J Biol Chem 1999; 274: 18492-502. https://doi.org/10.1074/jbc.274.26.18492

Protein modification by methylglyoxal: chemical nature and synthetic mechanism of a major fluorescent adduct; I. N. Shipanova, M. A. Glomb and R. H. Nagaraj; Archives of biochemistry and biophysics 1997; 344: 29-36. https://doi.org/10.1006/abbi.1997.0195

Novel modifications of Nα-boc-arginine and Nα-CBZ-lysine by methylglyoxal; Y. Al-Abed, T. Mitsuhashi, P. Ulrich and R. Bucala; Bioorganic & Medicinal Chemistry Letters 1996; 6: 1577-1578. https://doi.org/10.1016/s0960-894x(96)00276-4

Synthetic Approach to Argpyrimidine as a Tool for Investigating Nonenzymatic Posttranslational Modification of Proteins; M. Matveenko and C. F. W. Becker; Synlett 2017; 28: 1950-1955. https://doi.org/10.1055/s-0036-1588225

Impaired Chaperone Activity of Human Heat Shock Protein Hsp27 Site-Specifically Modified with Argpyrimidine; M. Matveenko, E. Cichero, P. Fossa and C. F. W. Becker; Ang. Chem. Int. Ed. 2016; 55: 11397-11402. https://doi.org/10.1002/anie.201605366

Random coil shifts of posttranslationally modified amino acids; A. C. Conibear, K. J. Rosengren, C. F. W. Becker and H. Kaehlig; Journal of Biomolecular NMR 2019; 73: 587-599. https://doi.org/10.1007/s10858-019-00270-4