Thermally stable copper(III)- and nickel(III)-tripeptide complexes and their photochemical decomposition in acid solution

Kirksey, Sanford T.; Neubecker, Thomas A.; Margerum, Dale W.

doi:10.1021/ja00500a063

Cited by 50 publications

(41 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Peptides that contain Aib in the third residue, GGAib, AAibAib and AibAibAib, do not form bis-complexes. Substitution of methyl groups for methylene hydrogens tends to increase the stability of peptide complexes; e.g., Ni(III) and Cu(III) complexes of GlyGlyAla are signifi cantly more stable than their triglycine analogs [249].…”

Section: Nickel(iii) Peptide Complexesmentioning

confidence: 99%

Nickel Ion Complexes of Amino Acids and Peptides

Kowalik-Jankowska

Kozłowski

Farkas

et al. 2007

Nickel and Its Surprising Impact in Nature

View full text Add to dashboard Cite

Section: Nickel(iii) Peptide Complexesmentioning

confidence: 99%

Nickel Ion Complexes of Amino Acids and Peptides

Kowalik-Jankowska

Kozłowski

Farkas

et al. 2007

Nickel and Its Surprising Impact in Nature

View full text Add to dashboard Cite

“…Seven examples are given in Table 3; these compounds have been synthesized by two or more groups of workers and there are few examples of duplicated experimental results lying within the normally accepted range of error (included in Table 3 are two examples where the results from different workers are in agreement). An explanation for the discrepancies in Table 3 may be the known abnormal behaviour of 2-methylalanyl peptides under various reaction conditions, including those commonly used in peptide synthesis (19)(20)(21). Whatever the explanation, it is clear that better methods of characterizing these peptides, either obtained by degradation of natural products or by synthesis, are required.…”

mentioning

confidence: 99%

The chemistry of peptides related to metabolites of Trichoderma spp. 2. An improved method of characterization of peptides of 2-methylalanine

Shaw¹,

Taylor²

1986

Can. J. Chem.

View full text Add to dashboard Cite

I. M. SHAW and A. TAYLOR. Can. J. Chem. 64, 164 (1986).4-Chlorobenzoylazide reacts with amino acid and peptide esters to give the 4-chlorobenzoyl derivatives in 60-90% yield, at room temperature, without measurable racemization. The reaction also proceeds smoothly with hindered amines such as methyl 2-methylalaninate and with secondary amines, e.g. methyl L-prolyl-L-valinate. Ten examples of the reaction are reported with peptides, synthesized for the purpose, that might be accessible from hydrolysates of the numerous fungal metabolites now known, which contain a high proportion of 2-methylalanine. The derivatives of di-, tri-, tetra-, and pentapeptides were highly crystalline, with sharp melting points, and could be detected and integrated in the effluent from chromatography columns at about the 10-ng level. This simple method of derivatization might be usefully applied to the resolution of discrepancies in the physical properties of ostensibly the same 2-methylalanyl peptide prepared in different laboratories.I. M. SHAW et A. TAYLOR. Can. J. Chem. 64, 164 (1986). L'azoture du chloro-4 benzoyle rkagit avec les esters d'acides aminks et de peptides, B la tempCrature ambiante, pour conduire aux dCrivks chloro-4 benzoylks avec des rendements de 60 i i 90% et sans rackmisation mesurable. La rkaction se produit aussi facilement avec des amines encombrkes, comme le mCthyl-2 alaninate de mkthyle, et avec des amines secondaires, comme le L-prolyl-L-valinate de mkthyle. On rapporte dix exemples de la reaction avec des peptides, synthCtisCs B cette fin, qui peuvent se retrouver dans les hydrolysats de plusieurs mktabolites de champignons qui sont maintenant connus pour contenir une grande proportion de mkthyl-2 alanine. Les dkrivCs des di-, tri-, tetra-et pentapeptides sont trks cristallins, ils ont des points de fusion bien dkfinis et ils peuvent itre dCtectks et intCgrCs en chromatographie a des niveaux de 10 ng. Cette simple mCthode de prkparer un dkrivC peut itre appliquke utilement B la rksolution des diffkrences dans les propriktks physiques de peptides de la methyl-2 alanine qui semblent les mimes, mais qui ont Ctk prCparCs dans des laboratoires diffkrents.

show abstract

“…13,14,26,27 The effectiveness of the Cu III G 4 formation and the synergistic effect of Ni(II) were more pronounced at pH 9, which can be explained by the different reactivity of Cu II G 4 complexes due to the different protonation degrees of the coordinated ligand. 28,33 In the present work, similar experiments were carried out focusing on the oxidation of Cu(II) complexes with GGA, G 3 , GGH, GHG, GHK and GGYR.…”

Section: Spectrophotometric Studies Of the Oxidation Of Cu(ii) Complementioning

confidence: 99%

“…Cu(II) peptide complexes can be oxidized to Cu(III) species, as demonstrated by Margerum and co-workers. [25][26][27] The peptides: glycylglycylhistidine (GGH), glycylhistidyllysine ( G H K ) , g l y cy l g l y cy l t y r o s y l a rg i n i n e ( G G Y R ) , glycylhistidylglycine (GHG), glycylglycyl-L-alanine (GGA), triglycine (G 3 ) and tetraglycine (G 4 ) were selected for this study in order to evaluate the probable role of trivalent copper in the DNA damage mechanism.…”

Section: Cumentioning

confidence: 99%