Kinetics and mechanism of the cleavage of the peptide bond next to asparagine
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Kinetics and mechanism of the cleavage of the peptide bond next to asparagine (266 views visite)

Capasso S, Mazzarella L, Sorrentino G, Balboni G, Kirby A

Peptides (ISSN: 0196-9781, 1873-5169electronic, 0196-9781linking), 1996; 17(6): 1075-1077.



Paper type Tipo di articolo: Journal Article,

Impact factor: 1.738, 5-year impact factor Impact factor a 5 anni: 2.372

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0029855624&partnerID=40&md5=b9e898a230bbe70b8933cdf7d088e19e

Keywords Parole chiave: Asparagine, Deamidation, Peptide Bond Cleavage, Succinimide, Article, Peptide Analysis, Priority Journal, Protein Processing, Kinetics, Models, Chemical, Oligopeptides, Protein Splicing,

Affiliations Affiliazioni:

Ctro. di Studio di B., CNR, Napoli, Italy
Facoltà di Sci. Ambientali, Seconda Università di Napoli, Caserta, Italy
Dipto. di Scienze Farmaceutiche, Università di Ferrara, Ferrara, Italy
University Chemical Laboratory, Cambridge, United Kingdom
Dipartimento di Chimica, via Mezzocannone 4, I-80134 Napoli, Italy
Facolt di Sci. Ambientali, Seconda Universit di Napoli, Caserta, Italy


References Riferimenti:

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Bolton, P.D., Hydrolysis of amides. II. Substituent effect in dilute acid and alkali (1966) Aust. J. Chem., 19, pp. 1013-1021

Brennan, T.W., Clarke, S., Mechanism of cleavage at Asn 148 during the maturation of Jack bean concanavalin A (1993) Biomed. Biophys. Res. Commun., 193, pp. 1031-1037

Capasso, S., Kirby, A.J., Salvadori, S., Sica, F., Zagari, A., Kinetics and mechanism of the reversible isomerization of aspartic acid residue in tetrapeptides (1995) J. Chem. Soc. Perkin Trans., 2, pp. 437-442

Capasso, S., Mazzarella, L., Sica, F., Zagari, A., Salvadori, S., Kinetic and mechanism of succinimide ring formation in the deamidation process of asparagine residues (1993) J. Chem. Soc. Perkin Trans., 2, pp. 679-682

Capasso, S., Sica, F., Zagari, A., Identification of aminosuccinyl residues in peptides by second-derivative ultraviolet spectrometry (1987) Peptides, 8, pp. 791-796

Connors, K.A., (1990) Chemical Kinetics, the Study of Reaction Rates in Solution, pp. 245-309. , New York: VCH

Geiger, T., Clarke, S., Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides (1987) J. Biol. Chem., 262, pp. 785-794

Koonin, E.V., A protein splice-junction motif in hedgehog family proteins (1995) Trends Biol. Sci., 20, pp. 141-142

Meinwald, C.Y., Stimson, E.R., Scheraga, H.A., Deamidation of the asparaginyl-glycyl sequence (1986) Int. J. Pept. Protein Res., 28, pp. 79-84

Molday, R.S., Kallen, R.G., Substituent effects on amide hydrogen exchange rates in aqueous solution (1972) J. Am. Chem. Soc., 94, pp. 6739-6745

Sondheimer, E., Holley, R.W., Imide from asparagine and glutamine (1954) J. Am. Chem. Soc., 76, pp. 2467-2470

Violand, B.N., Schlittler, M.R., Toren, P.C., Siegel, N.R., Formation of isoaspartate 99 in bovine and porcine somatotropins (1990) J. Prot. Chem., 9, pp. 109-117

Willi, A.V., Homogeneous catalysis of organic reactions (mainly acid-base) (1977) Comprehensive Chemical Kinetics, 8, pp. 1-95. , Bamford, C. H.

Tipper, C. F. H., Eds. Amsterdam: Elsevier

Bhatt, N. P., Patel, K., Borchardt, R. T., Chemical pathways of peptide degradation. I. Deamidation of adrenocorticotropic hormone (1990) Pharm. Res., 7, pp. 593-59

Bolton, P. D., Hydrolysis of amides. II. Substituent effect in dilute acid and alkali (1966) Aust. J. Chem., 19, pp. 1013-1021

Brennan, T. W., Clarke, S., Mechanism of cleavage at Asn 148 during the maturation of Jack bean concanavalin A (1993) Biomed. Biophys. Res. Commun., 193, pp. 1031-1037

Connors, K. A., (1990) Chemical Kinetics, the Study of Reaction Rates in Solution, pp. 245-309. , New York: VCH

Koonin, E. V., A protein splice-junction motif in hedgehog family proteins (1995) Trends Biol. Sci., 20, pp. 141-142

Meinwald, C. Y., Stimson, E. R., Scheraga, H. A., Deamidation of the asparaginyl-glycyl sequence (1986) Int. J. Pept. Protein Res., 28, pp. 79-84

Molday, R. S., Kallen, R. G., Substituent effects on amide hydrogen exchange rates in aqueous solution (1972) J. Am. Chem. Soc., 94, pp. 6739-6745

Violand, B. N., Schlittler, M. R., Toren, P. C., Siegel, N. R., Formation of isoaspartate 99 in bovine and porcine somatotropins (1990) J. Prot. Chem., 9, pp. 109-117

Willi, A. V., Homogeneous catalysis of organic reactions (mainly acid-base) (1977) Comprehensive Chemical Kinetics, 8, pp. 1-95. , Bamford, C. H.



The spontaneous cleavage reaction of the tetrapeptide Piv-Gly Asn-Sar-Gly-NHtBu to the C-terminal dipeptide and N-terminal succinimide dipeptide proceeds through pre-equilibrium deprotonation of the amide group of the asparagine side chain, Followed by intramolecular nucleophilic attack of nitrogen on the peptide carbonyl carbon atom. General acid-catalyzed breakdown of the intermediate then gives the products. According to this mechanism, the reaction rate strongly increases with pH and buffer concentration.
No results. Nessun risultato.
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Fonti R, Cheung N-KV, Bridger GJ, Guo H-F, Abrams MJ, Larson SM
99mTc-monoclonal antibody radiolabeled via hydrazino nicotinamide derivative for imaging disialoganglioside G(D2)-positive tumors (245 visite)
Nucl Med Biol (ISSN: 0969-8051, 0883-2897), 1999; 26(6): 681-686.
Impact Factor: 1.623
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Kramer RZ, Vitagliano L, Bella J, Berisio R, Mazzarella L, Brodsky B, Zagari A, Berman HM
X-ray crystallographic determination of a collagen-like peptide with the repeating sequence (Pro-Pro-Gly) (297 visite)
J Mol Biol (ISSN: 0022-2836, 1089-8638, 1089-8638electronic), 1998 Jul 24; 280(4): 623-638.
Impact Factor: 5.803
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De Simone G, Lombardi A, Galdiero S, Nastri F, Della Morte R, Staiano N, Pedone C, Bolognesi M, Pavone V
Hirunorms Are True Hirudin Mimetics. The Crystal Structure Of Human Alpha-Thrombin-Hirunorm V Complex (396 visite)
Protein Sci (ISSN: 0961-8368, 1469-896xelectronic), 1998 Feb; 7(2): 243-253.
Impact Factor: 4.44
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Arena G, Conato C, Contino A, Pulidori F, Purrello R, Remelli M, Tabbì G
Cu(II)-L-glutamine and L-asparagine binary complexes. A thermodynamic and spectroscopic study (231 visite)
Ann Chim (ISSN: 0003-4592), 1998 Jan; 88(1-2): 1-12.
Impact Factor: 0.811
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Capasso S, Di Donato A, Esposito L, Sica F, Sorrentino G, Vitagliano L, Zagari A, Mazzarella L
Deamidation in proteins: The crystal structure of bovine pancreatic ribonuclease with an isoaspartyl residue at position 67 (318 visite)
J Mol Biol (ISSN: 0022-2836, 1089-8638, 1089-8638electronic), 1996; 257(3): 492-496.
Impact Factor: 5.673
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Bonomo RP, De Flora A, Rizzarelli E, Santoro AM, Tabbì G, Tonetti M
Copper(II) complexes encapsulated in human red blood cells (470 visite)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 1995 Sep; 59(4): 773-784.
Impact Factor: 1.342
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Costanzo LL, De Guidi G, Giuffrida S, Sortino S, Condorelli G, Pappalardo G
Antioxidant effect of copper(II) on photosensitized lipid peroxidation (502 visite)
J Chem Res (ISSN: 0162-0134print, 0162-0134linking, 1873-3344), 1995 Feb; 57(2): 115-125.
Impact Factor: 1.342
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Vinci C, Caltabiano V, Santoro AM, Rabuazzo AM, Buscema M, Purrello R, Rizzarelli E, Vigneri R, Purrello F
Copper Addition Prevents The Inhibitory Effects Of Interleukin 1-Beta On Rat Pancreatic Islets (370 visite)
Diabetologia, 1995 Jan; 38(1): 39-45.
Impact Factor: 0
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Pavone V, Lombardi A, Saviano M, Di Blasio B, Nastri F, Fattorusso R, Zaccaro L, Maglio O, Yamada T, Omote Y
Mixed conformation in C(α, α)-disubstituted tripeptides: X-ray crystal structures of Z-Aib-Dph-Gly-OMe and Bz-Dph-Dph-Gly-OMe (293 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1994 Dec; 34(12): 1595-1604.
Impact Factor: 2.425
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Rossi F, Saviano M, Di Blasio B, Zanotti G, Maione AM, Tancredi T, Pedone C
BIOACTIVE PEPTIDES - SOLID-STATE, SOLUTION AND MOLECULAR-DYNAMICS STUDIES OF A CYCLOLINOPEPTIDE-A RELATED CYSTINYL CYCLOPENTAPEPTIDE (381 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1994 Feb; 34(2): 273-284.
Impact Factor: 2.425
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Di Blasio B, Lombardi A, D'Auria G, Saviano M, Isernia C, Maglio O, Paolillo L, Pedone C, Pavone V
Beta-Alanine Containing Peptides: Gamma-Turns In Cyclotetrapeptides (455 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1993 Apr; 31(10): 621-631.
Impact Factor: 2.425
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Alberghina M, Lupo G, La Spina G, Mangiameli A, Gulisano M, Sciotto D, Rizzarelli E
Cytoprotective effect of copper(II) complexes against ethanol-induced damage to rat gastric mucosa (356 visite)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 1992 Mar; 45(4): 245-259.
Impact Factor: 1.342
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54 Records (53 escludendo Abstract e Conferenze).
Impact factor totale: 232.4 (231.058 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 245.36 (241.978 escludendo Abstract e Conferenze).







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