Peptides containing histidine

Figure 2.12 Amidate complexes of histidine containing peptides, (19) and (20), and of amides of EDTA, (21).

Tanokura M (1983) 1 II-NMstudy R on the tautomerism of the imidazole ring of histidine residues I. Microscopic pK values and molar ratios of tautomers in histidine-containing peptides. Biochim Biophys Acta 742 576-585. 

Amini, A., Chakraborty, A., Regnier, F.E. (2002). Simplification of complex tryptic digests for capillary electrophoresis by affinity selection of histidine-containing peptides with immobilized metal ion affinity chromatography. J. Chromatogr. B 772, 35-44. 

Figure 2.5 The cisplatin reactive group can covalently couple to methionine-, cysteine-, and histidine-containing peptides or proteins. It also reacts with guanine groups to form a covalent modification on the N7 nitrogen.

GC Windridge, EC Jorgensen. Racemization in the solid phase synthesis of histidine containing peptides. Intra-Sci Chem Rep 5, 375, 1971. 

Photki and Sakarellou-Daitsiotou 85) synthesized the series of histidine-containing peptides shown below ... 

Orioli, M., Aldini, G., Beretta, G., Mattei Facino, R., and Carini, M. (2005). LC-ESI-MS/MS determination of 4-hydroxy-trans-2-nonenal Michael adducts with cysteine and histidine-containing peptides as early markers of oxidative stress inexcitable tissues. ]. Chromatogr. B Arnlyt. Technol. Biomed. Life Sci. 827,109-118. 

Solid phase attachment of histidine-containing peptides by anchoring the imidazole ring to trityl resins has been developed for combinatorial library preparation of diketopiperazines <99TL809>. Histidine, histamine, and urocanic acid are edl imidazole-containing molecules that have been attached to a trityl-type resin to allow their application to combinatorial chemistry <99TL2825>. 

Chen, H. M., Muramoto, K., Yamauchi, F., Fujimoto, K., and Nokihara, K. (1998). Antiox-idative properties of histidine-containing peptides designed from peptide fragments found in the digests of a soybean protein. J. Agric. Food Chem. 46, 49-53. 

Halomethyl ketones and acids are known to react with thiols and imidazoles. TPCK reacts far more rapidly with chymotrypsin than it does with normal histidine-containing peptides because of its high reactivity as an affinity label. This can be seen in Table 9.2 for an analogous chloromethyl ketone. In addition to this important diagnostic feature, the irreversible inhibition of chymotrypsin by TPCK has four other characteristic features 1,4... 

H NMR spectra of neutral histidines and histidine-containing peptides... 

Guevara-Garcia, J.A., N. Barba-Behrens, R. Contreras, and G. Mendosa-Diaz. 1998. Bis-peroxo-oxovanadium(V) complexes of histidine-containing peptides as models for vanadium haloperoxidases. In Vanadium Compounds Chemistry, Biochemistry and Therapeutic Applications. A.S. Tracey and D.C. Crans (Eds). American Chemical Society, Washington, D.C. 126-35. 

Capper (II) Transfer from Serum Albumin (13). The kinetics of transfer of Cu(II) from its complexes with human serum albumin, bovine serum albumin, gly-gly-his, gly-gly-his-gly, and asp ala his Tys to trien all exhibit parallel behavior. The histidine-containing peptides model the first Cu(II) binding site in the serum albumins, where Cu(II) is coordinated to the amine terminal, to two deprotonated peptide nitrogens,... 

Metal ions can enhance the resolution of nucleic acids and amino acids in MECC. Zinc perchlorate (0-30 mM) has been found useful as a complexing reagent for histidine-containing peptides. 

Bryce, G. F., and F. R. N. Gurd Visible spectra and optical rotary properties of cupric ion complexes of L-histidine-containing peptides. J. Biol. Chem. 241, 122 (1966). 

The synthesis of histidine-containing peptides without protection of the imidazole side chains is feasible, but it can be inconvenient and unsatisfactory because of the basic, nucleophilic and hydrophihc character of such side chains. /w-Nitrogens can react with electrophilic reagents such as Ar,AT -dicyclohexylcarbodiimide,W catalyze undesirable acyl-transfer reactions,Pl and cause loss of chiral integrity at the histidine a-carbon.t l Side-chain protection has therefore generally been employed. 

A review on NMR of Cu(ll) complex with histidine-containing peptides has appeared <2003MRC877>. 

Levine-Pinto, H., Bouabdallah, B., Morgat, J. L., el al. (1981) Specific and direct fluorination of an histidine-containing peptide thyroliberin. Biochemical and Biophysical Research Communications, 103, 1121-1130. 

Figure 7. Liposome-assisted catalysis. (A) Dependency of the initial hydrolysis rate of C16-O Np (nitrophenyl-pamitate) catalyzed by 1 mM carbobenzoxy-Phe-His-Leu-OH on the substrate concentration, in 0.05 M borate buffer pH 8.5. The filled circles are relative to the self-hydrolysis (no peptide, no liposomes). Open triangles are without liposomes, open squares with liposomes. (B) The pseudo-enzymatic turnover of the catalytically active liposomes. The catalytic activity results primarily from the binding (and solubilization) of a very hydrophobic histidin-containing peptide and the very hydrophobic substrate.

Direct trifluoromethylation of the imidazole ring of histidine-containing peptides has been achieved photochemically using trifluoroiodomethane,and the products of photoreaction of primary aromatic amines with chloromethanes have been identified. ... 

Midoux P, LeCam E, Coulaud D, et al. (2002). Histidine containing peptides and polypeptides as nucleic acid vectors. Somat Cell Molec. Genetics. 27 27-47. 

Khossravi M, Borchardt R T (2000). Chemical pathways of peptide degradation. X Effect of metal catalyzed oxidation on the solntion strnctnre of a histidine-containing peptide fragment of hnman relaxin. Pharm. Res. 17 851-858. 

An early example of this approach was that of Lautsch et al. who coupled various histidine-containing tripeptides to the propionic acid side-chains of mesoporphyrin IX la (Scheme 2). After metal insertion into the porphyrin, intramolecular coordination by the histidyl imidazole was possible depending on the length of the peptide chain. Similarly, histidine-containing peptides were attached to the ethyl side chains of mesoporphyrin IX via sulfide linkages to give 2(b-d), a situation similar to that in cytochrome c. Losse and Miiller coupled L-histidine methylester and protohemin 3 with dicyclohexylcar-... 

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