Kinetics of Isomerization and Inversion of Aspartate 58 of αA-Crystallin Peptide Mimics under Physiological Conditions

PLoS ONE

Volumn 8, Issue 3, 2013, Pages

  Aki, Kenzo ^a   Fujii, Norihiko ^a   Fujii, Noriko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CRYSTALLIN; ASPARTATE 58; ASPARTIC ACID; SUCCINIMIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; HUMAN; HYDROLYSIS KINETICS; ISOMERIZATION; PHASE SEPARATION; PROTEIN DETERMINATION; PROTEIN HYDROLYSIS; PROTEIN PURIFICATION; RACEMIZATION; RESIDUE ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEQUENCE ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ADOLESCENT; ADULT; AGED; AGED, 80 AND OVER; AGING; ALPHA-CRYSTALLIN A CHAIN; ASPARTIC ACID; CHILD; CHILD, PRESCHOOL; COMPUTER SIMULATION; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; INFANT; INFANT, NEWBORN; KINETICS; LIFE EXPECTANCY; MIDDLE AGED; MODELS, THEORETICAL; MOLECULAR MIMICRY; PEPTIDES; STEREOISOMERISM; SUCCINIMIDES; TEMPERATURE; YOUNG ADULT;

EID: 84874707855     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0058515     Document Type: Article

References (26)

1. Masters PM, Bada JL, Zigler JS Jr, (1978) Aspartic acid racemization in heavy molecular weight crystallins and water insoluble protein from normal human lenses and cataracts. Proc Natl Acad Sci U S A 75: 1204-1208.
2. Fujii N, Satoh K, Harada K, Ishibashi Y, (1994) Simultaneous stereoinversion and isomerization at specific aspartic acid residues in alpha A-crystallin from aged human lens. J Biochem 116: 663-669.
3. Fujii N, Ishibashi Y, Satoh K, Fujino M, Harada K, (1994) Simultaneous racemization and isomerization at specific aspartic acid residues in alpha B-crystallin from the aged human lens. Biochim Biophys Acta 1204: 157-163.
4. Fujii N, Kawaguchi T, Sasaki H, Fujii N, (2011) Simultaneous stereoinversion and isomerization at the Asp-4 residue in betaB2-crystallin from the aged human eye lenses. Biochemistry 50: 8628-8635.
5. Kaji Y, Oshika T, Takazawa Y, Fukayama M, Takata T, et al. (2007) Localization of D-beta-aspartic acid-containing proteins in human eyes. Invest Ophthalmol Vis Sci 48: 3923-3927.
6. Kaji Y, Oshika T, Okamoto F, Fujii N, (2009) Immunohistochemical localisation of D-beta-aspartic acid in pingueculae. Br J Ophthalmol 93: 974-976.
7. Kaji Y, Oshika T, Takazawa Y, Fukayama M, Fujii N, (2009) Immunohistochemical localisation of D-beta-aspartic acid-containing proteins in climatic droplet keratopathy. Br J Ophthalmol 93: 977-979.
8. Helfman PM, Bada JL, (1976) Aspartic acid racemisation in dentine as a measure of ageing. Nature 262: 279-281.
9. Powell JT, Vine N, Crossman M, (1992) On the accumulation of D-aspartate in elastin and other proteins of the ageing aorta. Atherosclerosis 97: 201-208.
10. Fisher GH, D'Aniello A, Vetere A, Cusano GP, Chavez M, et al. (1992) Quantification of D-aspartate in normal and Alzheimer brains. Neurosci Lett 143: 215-218.
11. Roher AE, Lowenson JD, Clarke S, Wolkow C, Wang R, et al. (1993) Structural alterations in the peptide backbone of beta-amyloid core protein may account for its deposition and stability in Alzheimer's disease. J Biol Chem 268: 3072-3083.
12. Ohtani S, Yamamoto T, Matsushima Y, Kobayashi Y, (1998) Changes in the amount of D-aspartic acid in the human femur with age. Growth Dev Aging 62: 141-148.
13. Cloos PA, Fledelius C, (2000) Collagen fragments in urine derived from bone resorption are highly racemized and isomerized: a biological clock of protein aging with clinical potential. Biochem J 345 Pt 3: 473-480.
14. Ritz-Timme S, Laumeier I, Collins M, (2003) Age estimation based on aspartic acid racemization in elastin from the yellow ligaments. Int J Legal Med 117: 96-101.
15. Fujii N, Tajima S, Tanaka N, Fujimoto N, Takata T, et al. (2002) The presence of D-beta-aspartic acid-containing peptides in elastic fibers of sun-damaged skin: a potent marker for ultraviolet-induced skin aging. Biochem Biophys Res Commun 294: 1047-1051.
16. Mori Y, Aki K, Kuge K, Tajima S, Yamanaka N, et al. (2011) UV B-irradiation enhances the racemization and isomerizaiton of aspartyl residues and production of Nepsilon-carboxymethyl lysine (CML) in keratin of skin. J Chromatogr B Analyt Technol Biomed Life Sci 879: 3303-3309.
17. Young GW, Hoofring SA, Mamula MJ, Doyle HA, Bunick GJ, et al. (2005) Protein L-isoaspartyl methyltransferase catalyzes in vivo racemization of Aspartate-25 in mammalian histone H2B. J Biol Chem 280: 26094-26098.
18. Fujii N, Harada K, Momose Y, Ishii N, Akaboshi M, (1999) D-amino acid formation induced by a chiral field within a human lens protein during aging. Biochem Biophys Res Commun 263: 322-326.
19. Fujii N, Shimmyo Y, Sakai M, Sadakane Y, Nakamura T, et al. (2007) Age-related changes of alpha-crystallin aggregate in human lens. Amino Acids 32: 87-94.
20. Miura Y, Fujimoto N, Komatsu T, Tajima S, Kawada A, et al. (2004) Immunohistochemical study of chronological and photo-induced aging skins using the antibody raised against D-aspartyl residue-containing peptide. J Cutan Pathol 31: 51-56.
21. Sadakane Y, Fujii N, Nakagomi K, (2011) Determination of rate constants for beta-linkage isomerization of three specific aspartyl residues in recombinant human alphaA-crystallin protein by reversed-phase HPLC. J Chromatogr B Analyt Technol Biomed Life Sci 879: 3240-3246.
22. Geiger T, Clarke S, (1987) Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides. Succinimide-linked reactions that contribute to protein degradation. J Biol Chem 262: 785-794.
23. Capasso S, (1996) Thermodynamic parameters of the reversible isomerization of aspartic residues via a succinimide derivative. Thermochimica Acta 286: 41-50.
24. Stephenson RC, Clarke S, (1989) Succinimide formation from aspartyl and asparaginyl peptides as a model for the spontaneous degradation of proteins. J Biol Chem 264: 6164-6170.
25. Tyler-Cross R, Schirch V, (1991) Effects of amino acid sequence, buffers, and ionic strength on the rate and mechanism of deamidation of asparagine residues in small peptides. J Biol Chem 266: 22549-22556.
26. Fujii N, Sakaue H, Sasaki H (2012) A rapid comprehensive LC-MS based survey of the Asp isomers in crystallins from human cataract lenses. J Biol Chem.