Abstract
Synthesis, characterization and antioxidant activity of a new series of chiral N-boc oraganotellurium compounds, (CH3)3OC(O)NHCH(R)C(O)NHCH2CH2Te-C6H4-4-OCH3, containing carbamate and peptide groups have been reported in this paper. These chiral peptides were synthesized in good to excellent yields, via acid-amine coupling reaction of N-boc L-amino acids with 2-(4-methoxyphenyltelluro) ethylamine in presence of dicyclohexyl carbodimide (DCC) at room temperature. The elemental analyses, Fourier transform infrared (FTIR), 1H and 13C {1H} nuclear magnetic resonance (NMR) spectra and mass spectra were characteristic. Specific optical rotation (SOR) was also determined. In vitro antioxidant activity of these multi-functional compounds in methanol has been evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with 2,6-di-tert-butyl-4-methylphenol (BHT) as a standard reference compound. The IC50 (inhibitory concentration 50) values of these chiral peptides revealed significant inhibition against DPPH radicals and found to be effective antioxidants.
Highlights
An antioxidant is “any substance that delays or prevents oxidation of an oxidisable species”.1,2 Oxidative stress, induced by reactive oxygen species (ROS) produced in the body, is one of the main factors of current slow killer diseases, that population suffering from, like cancer, diabetes, cardiovascular, neurological (Alzheimer’s and Parkinson’s), inflammatory viral diseases and digestive disorders.[3,4,5,6]Since the discovery of “Ebselen”, a natural antioxidant, a number of organochalcogen (S, Se, Te) compounds have been designed, synthesized and investigated as free radical scavengers or antioxidants to mimic the natural ones.[7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30] The divalent organochalcogen compounds have the potential to act as catalytic antioxidants because they readily react with many types of oxidants such as peroxides, peroxynitrites, singlet oxygen and ozone resulting tetravalent organochalcogens (that is chalcogenides to chalcogenoxides and chalcogenols to dichalcogenides) which in turn reduced by many mild reducing agents
A new series of chiral N-boc organotellurated compounds (4a-4g, Figure 1) were synthesized by condensation of N-boc L-amino acids and 2-(4-methoxyphenyltelluro) ethylamine in presence of dicyclohexyl carbodimide (DCC) as a dehydrating agent according to the reactions given in the Scheme 1
We presented the synthesis of new chiral N-boc oraganotellurium compounds (4a-4g) containing carbamate and peptide groups from N-boc L-amino acids and 2-(4-methoxyphenyltelluro) ethylamine in presence of DCC
Summary
An antioxidant is “any substance that delays or prevents oxidation of an oxidisable species”.1,2 Oxidative stress, induced by reactive oxygen species (ROS) produced in the body, is one of the main factors of current slow killer diseases, that population suffering from, like cancer, diabetes, cardiovascular, neurological (Alzheimer’s and Parkinson’s), inflammatory viral diseases and digestive disorders.[3,4,5,6]Since the discovery of “Ebselen”, a natural antioxidant, a number of organochalcogen (S, Se, Te) compounds have been designed, synthesized and investigated as free radical scavengers or antioxidants to mimic the natural ones.[7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30] The divalent organochalcogen compounds have the potential to act as catalytic antioxidants because they readily react with many types of oxidants such as peroxides, peroxynitrites, singlet oxygen and ozone resulting tetravalent organochalcogens (that is chalcogenides to chalcogenoxides and chalcogenols to dichalcogenides) which in turn reduced by many mild reducing agents. Characterization and in vitro Antioxidant Activity of New Chiral N-boc Organotellurium Compounds
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