Methods of the site-selective solid phase synthesis of peptide-derived Amadori products

Amino Acids

Volumn 38, Issue 3, 2010, Pages 881-889

  Stefanowicz, Piotr ^a   Kijewska, Monika ^a   Kapczyńska, Katarzyna ^a   Szewczuk, Zbigniew ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

Amadori rearrangement; Enzymatic stability; Glycation; Solid phase peptide synthesis

Indexed keywords

2,3:4,5 DI O ISOPROPYLIDENE BETA DEXTRO ARABINO HEXOS 2 ULO 2,6 PYRANOSE; CARBOHYDRATE; CYANOBOROHYDRIDE SODIUM; LYSINE; PEPTIDE DERIVATIVE; SODIUM CYANIDE; UNCLASSIFIED DRUG;

ALKYLATION; AMADORI REARRANGEMENT; ARTICLE; BETA TURN; CIRCULAR DICHROISM; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN GLYCOSYLATION; PROTEIN HYDROLYSIS; PROTEIN STRUCTURE; REDUCTION; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; FRUCTOSE; GLYCOSYLATION; GLYCOSYLATION END PRODUCTS, ADVANCED; LYSINE; MAILLARD REACTION; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; PROTEIN CONFORMATION; SERUM ALBUMIN, BOVINE; SOLVENTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 77951665751     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-009-0294-z     Document Type: Article

References (25)

1. N Ahmed PJ Thornalley 2003 Quantitative screening of protein biomarkers of early glycation, advanced glycation, oxidation and nitrosation in cellular and extracellular proteins by tandem mass spectrometry multiple reaction monitoring Biochem Soc Trans 31 1417 1422 10.1042/BST0311417 10.1042/BST0311417 1:CAS:528:DC%2BD3sXps12jtL8%3D 14641078 (Pubitemid 38030990)
2. JW Brock DJ Hinton WE Cotham TO Metz SR Thorpe JW Baynes JM Ames 2003 Proteomic analysis of the site specificity of glycation and carboxymethylation of ribonuclease J Proteome Res 2 506 513 10.1021/pr0340173 10.1021/pr0340173 1:CAS:528:DC%2BD3sXkvFyjs7k%3D 14582647 (Pubitemid 37376845)
3. Chan Weng C, White PD (eds) (1999) Fmoc solid phase peptide synthesis: a practical approach. Oxford University Press, Oxford
4. II Cubero MTP Lopez-Espinosa 1990 Enantiospecific synthesis of spiroacetals. 1. An enantiospecific synthesis of (-)-talaromycin-A and (-)-talaromycin-B from d-fructose Carbohydr Res 205 293 304 10.1016/0008- 6215(90)80148-V 10.1016/0008-6215(90)80148-V
5. NJ Forrow MJ Batchelor 1990 Synthesis of the N-glycopeptide partial sequence A(1)-A(12) of the β-chain of glycosylated hemoglobin HBA1C - a new approach to Amadori N-glycopeptides Tetrahedron 31 3493 3494 10.1016/S0040-4039(00)97431-8 10.1016/S0040-4039(00)97431-8 1:CAS:528: DyaK3cXlvFWqtrw%3D (Pubitemid 20188150)
6. A Frolov R Hoffmann 2008 Separation of Amadori peptides from their unmodified analogs by ion-pairing RP-HPLC with heptafluorobutyric acid as ion-pair reagent Anal Bioanal Chem 392 1209 1214 10.1007/s00216-008-2377-1 10.1007/s00216-008-2377-1 1:CAS:528:DC%2BD1cXht1yqsbrN 18813915
7. A Frolov P Hoffmann R Hoffmann 2006 Fragmentation behavior of glycated peptides derived from d-glucose, d-fructose, and d-ribose in tandem mass spectrometry J Mass Spectrom 41 1459 1469 10.1002/jms.1117 10.1002/jms.1117 1:CAS:528:DC%2BD28XhtlWqs7bP 17063450 (Pubitemid 44875656)
8. A Frolov D Singer R Hoffmann 2006 Site-specific synthesis of Amadori-modified peptides on solid phase J Pept Sci 12 389 395 10.1002/psc.739 10.1002/psc.739 1:CAS:528:DC%2BD28XmvVWqs7o%3D 16342332 (Pubitemid 43933226)
9. A Frolov D Singer R Hoffmann 2007 Solid-phase synthesis of glucose-derived Amadori peptides J Pept Sci 13 862 867 10.1002/psc.901 10.1002/psc.901 1:CAS:528:DC%2BD1cXkslyksg%3D%3D 17883244 (Pubitemid 350303225)
10. S Horvat A Jakas 2004 Peptide and amino acid glycation: new insights into the Maillard reaction J Pept Sci 10 119 137 10.1002/psc.519 10.1002/psc.519 1:CAS:528:DC%2BD2cXjsFertLc%3D 15113085 (Pubitemid 38477090)
11. MJ Howard CM Smales 2005 NMR analysis of synthetic human serum albumin alpha-helix 28 identifies structural distortion upon amadori modification J Biol Chem 280 22582 22589 10.1074/jbc.M501480200 10.1074/jbc.M501480200 1:CAS:528:DC%2BD2MXltVyhsL8%3D 15837789 (Pubitemid 40853161)
12. A Lapolla D Fedele R Reitano NC Arico R Seraglia P Traldi E Marotta R Tonani 2004 Enzymatic digestion and mass spectrometry in the study of advanced glycation end products/peptides J Am Soc Mass Spectrom 15 496 509 10.1016/j.jasms.2003.11.014 10.1016/j.jasms.2003.11.014 1:CAS:528: DC%2BD2cXisVGhurs%3D 15047055 (Pubitemid 38407135)
13. DL Mendez RA Jensen LA McElroy JM Pena RM Esquerra 2005 The effect of non-enzymatic glycation on the unfolding of human serum albumin Arch Biochem Biophys 444 92 99 10.1016/j.abb.2005.10.019 10.1016/j.abb.2005.10.019 1:CAS:528:DC%2BD2MXht1OltL%2FN 16309624 (Pubitemid 41728341)
14. PI Moreira MA Smith XW Zhu A Nunomura RJ Castellani G Perry 2005 Oxidative stress and neurodegeneration Ann N Y Acad Sci 1043 545 552 10.1196/annals.1333.062 10.1196/annals.1333.062 1:CAS:528:DC%2BD2MXpvVKqtLk%3D 16037277 (Pubitemid 41123944)
15. MA Mosier JR Occhipinti NL Burstein 1986 Autofluorescence of the crystalline lens in diabetes Arch Ophthalmol 104 1340 1343 1:STN:280: DyaL28zit1KnsQ%3D%3D 3753285
16. G Munch M Gerlach J Sian A Wong P Riederer 1998 Advanced glycation end products in neurodegeneration: more than early markers of oxidative stress? Ann Neurol 44 S85 S88 1:CAS:528:DyaK1cXmtFGktrw%3D 9749578 (Pubitemid 28423833)
17. A Perczel M Hollosi BM Foxman GD Fasman 1991 Conformational-analysis of pseudocyclic hexapeptides based on quantitative circular dichroism (CD), NOE, and X-ray data - the pure CD spectra of type-I and type-II β-turns J Am Chem Soc 113 9772 9784 10.1021/ja00026a010 10.1021/ja00026a010 1:CAS:528:DyaK3MXmvVSmsL4%3D
18. JF Povey MJ Howard RA Williamson CM Smales 2008 The effect of peptide glycation on local secondary structure J Struct Biol 161 151 161 10.1016/j.jsb.2007.10.004 10.1016/j.jsb.2007.10.004 1:CAS:528: DC%2BD1cXptlCgtw%3D%3D 18036831
19. M Roscic S Horvat 2006 Transformations of bioactive peptides in the presence of sugars-characterization and stability studies of the adducts generated via the Maillard reaction Bioorg Med Chem 14 4933 4943 10.1016/j.bmc.2006.03.006 10.1016/j.bmc.2006.03.006 1:CAS:528: DC%2BD28XltFOmurw%3D 16563774 (Pubitemid 43767125)
20. P Stefanowicz J Boratyński U Kańska I Petry Z Szewczuk 2001 Evaluation of high temperature glycation of proteins and peptides by electrospray ionization mass spectrometry Acta Biochim Pol 48 1137 1142 1:CAS:528:DC%2BD38XhsFKrt7k%3D 11995980 (Pubitemid 33602368)
21. P Stefanowicz K Kapczyńska A Kluczyk Z Szewczuk 2007 A new procedure for the synthesis of peptide-derived Amadori products on a solid support Tetrahedron Lett 48 967 969 10.1016/j.tetlet.2006.12.022 10.1016/j.tetlet.2006.12.022 1:CAS:528:DC%2BD2sXnvFGnsA%3D%3D (Pubitemid 46072990)
22. SR Thorpe JW Baynes 1996 Role of Maillard reaction in diabetes mellitus and diseases of aging Drugs Aging 9 69 77 10.2165/00002512-199609020-00001 10.2165/00002512-199609020-00001 1:STN:280:DyaK28vhvVSjtQ%3D%3D 8820792
23. E Vass M Hollosi M Kveder B Kojic-Prodic M Cudic S Horvat 2000 Spectroscopic evidence of β-turn in N-glycated peptidomimetics related to leucine-enkephalin Spectrochim Acta A Mol Biomol Spectrosc 56 2479 2489 10.1016/S1386-1425(00)00336-X 10.1016/S1386-1425(00)00336-X
24. Woody RW (1985) Circular dichroism of peptides. In: Hruby VJ, Meienhofer J (eds) The peptides, vol 7. Academic Press, New York, pp 16-114
25. QB Zhang A Frolov N Tang R Hoffmann T van de Goor TO Metz RD Smith 2007 Application of electron transfer dissociation mass spectrometry in analyses of non-enzymatically glycated peptides Rapid Commun Mass Spectrom 21 661 666 10.1002/rcm.2884 10.1002/rcm.2884 1:CAS:528:DC%2BD2sXis12hsrY%3D 17279487 (Pubitemid 46340309)