ABSTRACT
Starting from branched para-benzoquinones a practical and highly flexible route is described for the preparation of unsaturated carbapyranoses. The potential of the synthesized galactose analogues to act as competitive inhibitors in lectin-carbohydrate interactions is investigated by means of Surface Plasmon Resonance (SPR) Spectroscopy.
Subject(s)
Carbasugars/chemistry , Lectins/chemistry , Carbasugars/chemical synthesis , Molecular StructureABSTRACT
Reactive oxygen molecules are formed in vivo as by-products of normal aerobic metabolism. All organisms dependent on oxygen are inevitably exposed to these species so that DNA damage can occur in both genomic and mitochondrial DNA (mtDNA). In order to determine endogenous DNA damage we have developed an analytical method that involves the isolation and hydrolysis of genomic DNA or mtDNA, the labeling of modified and unmodified nucleotides and micellar electrokinetic chromatography with laser-induced fluorescence detection. With this method we have found etheno-adenine, thymine glycol, uracil, hypoxanthine, and 5-methylcytosine. These were identified by the addition of internal standards to the genomic or mtDNA. There are a large number of other signals in the electropherograms of mtDNA that we have never found in genomic DNA analysis because they are at lower concentration in the genome. In the DNA of untreated patients with chronic lymphocytic leukemia (CLL), uracil and high levels of etheno-adenine were found, which can be explained by antioxidant enzyme alterations and oxidative stress in the CLL lymphocytes.
Subject(s)
DNA Adducts/isolation & purification , DNA Damage , DNA, Mitochondrial/chemistry , Electrophoresis, Capillary/methods , Genome , 5-Methylcytosine/analysis , 5-Methylcytosine/isolation & purification , Adenosine Monophosphate/analogs & derivatives , Adenosine Monophosphate/analysis , Adenosine Monophosphate/isolation & purification , Animals , Biomarkers/analysis , Cattle , Chromatography, Micellar Electrokinetic Capillary/methods , DNA Adducts/analysis , DNA Methylation , Humans , Lasers , Leukemia, Lymphocytic, Chronic, B-Cell/metabolism , Liver/chemistry , Oxidative Stress , Spectrometry, FluorescenceABSTRACT
A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.
