desmosine and pyridine

desmosine has been researched along with pyridine* in 2 studies

Other Studies

2 other study(ies) available for desmosine and pyridine

Article	Year
Biomimetic Chichibabin pyridine synthesis of the COPD biomarkers and elastin cross-linkers isodesmosine and desmosine. Organic letters, 2014, Mar-21, Volume: 16, Issue:6 The tetrasubstituted pyridinium amino acids isodesmosine and desmosine are cross-linkers of elastin and are attractive biomarkers for the diagnosis of chronic obstructive pulmonary disease (COPD). In this study, the biomimetic total synthesis of isodesmosine and desmosine via a lanthanide-promoted Chichibabin pyridine synthesis using the corresponding aldehyde and amine hydrochloride is reported. Topics: Biomarkers; Biomimetics; Cross-Linking Reagents; Desmosine; Elastin; Humans; Isodesmosine; Lanthanoid Series Elements; Molecular Structure; Pulmonary Disease, Chronic Obstructive; Pyridines; Pyridinium Compounds	2014
Oxodesmosine and isooxodesmosine, candidates of oxidative metabolic intermediates of pyridinium cross-links in elastin. Archives of biochemistry and biophysics, 2001, Jan-01, Volume: 385, Issue:1 We isolated two new dihydrooxopyridine cross-links, oxodesmosine (OXD) and isooxodesmosine (IOXD) from the acid hydrolysates of the bovine aortic elastin. OXD and IOXD were identified to have N-substituted 1,2-dihydro-2-oxopyridine and N-substituted 1,4-dihydro-4-oxopyridine skeletons, respectively, with three alpha-amino acid groups and mass of 495 (C23H37N5O7). These structures and distribution indicated that OXD and IOXD are oxidative metabolites generated from desmosine (DES) and isodesmosine (IDE), respectively, by reactive oxygen species (ROS). Effects of ROS derived from divalent metal (Fe2+, Cu2+)/H2O2 on DES, IDE, OXD, and IOXD in elastin were investigated. Changes in the contents of these cross-links in elastin were observed by using reverse-phase HPLC with UV detection. The time- and pH-dependent formation of OXD and reduction of DES and IDE in elastin by Cu2+/H2O2 and Fe2+/H2O2 were observed. OXD was found to be formed from DES by Fe2+/H2O2. No formation of IOXD was observed under the conditions of oxidation examined. By using a model compound of IDE, however, we found that 4-pyridone could be formed by Fe2+/H2O2. Elastin incubated in Cu2+/H2O2 was also solubilized dependent on solution pH and the concentration of H2O2. These results suggest that oxidative degradation of elastin with cross-links results in its weakening, followed by its solubilization. Pyridinium cross-links, such as DES and IDE, may be oxidatively metabolized by ROS, further changing to dihydrooxopyridine cross-links such as OXD and IOXD, respectively. Topics: Animals; Aorta; Cattle; Chromatography, High Pressure Liquid; Cross-Linking Reagents; Desmosine; Elastin; Hydrogen Peroxide; Hydrogen-Ion Concentration; Magnetic Resonance Spectroscopy; Models, Chemical; Oxygen; Pyridines; Spectrophotometry; Time Factors; Ultraviolet Rays	2001

Article

Year

Biomimetic Chichibabin pyridine synthesis of the COPD biomarkers and elastin cross-linkers isodesmosine and desmosine.

Organic letters, 2014, Mar-21, Volume: 16, Issue:6

The tetrasubstituted pyridinium amino acids isodesmosine and desmosine are cross-linkers of elastin and are attractive biomarkers for the diagnosis of chronic obstructive pulmonary disease (COPD). In this study, the biomimetic total synthesis of isodesmosine and desmosine via a lanthanide-promoted Chichibabin pyridine synthesis using the corresponding aldehyde and amine hydrochloride is reported.

Topics: Biomarkers; Biomimetics; Cross-Linking Reagents; Desmosine; Elastin; Humans; Isodesmosine; Lanthanoid Series Elements; Molecular Structure; Pulmonary Disease, Chronic Obstructive; Pyridines; Pyridinium Compounds

2014

Oxodesmosine and isooxodesmosine, candidates of oxidative metabolic intermediates of pyridinium cross-links in elastin.

Archives of biochemistry and biophysics, 2001, Jan-01, Volume: 385, Issue:1

We isolated two new dihydrooxopyridine cross-links, oxodesmosine (OXD) and isooxodesmosine (IOXD) from the acid hydrolysates of the bovine aortic elastin. OXD and IOXD were identified to have N-substituted 1,2-dihydro-2-oxopyridine and N-substituted 1,4-dihydro-4-oxopyridine skeletons, respectively, with three alpha-amino acid groups and mass of 495 (C23H37N5O7). These structures and distribution indicated that OXD and IOXD are oxidative metabolites generated from desmosine (DES) and isodesmosine (IDE), respectively, by reactive oxygen species (ROS). Effects of ROS derived from divalent metal (Fe2+, Cu2+)/H2O2 on DES, IDE, OXD, and IOXD in elastin were investigated. Changes in the contents of these cross-links in elastin were observed by using reverse-phase HPLC with UV detection. The time- and pH-dependent formation of OXD and reduction of DES and IDE in elastin by Cu2+/H2O2 and Fe2+/H2O2 were observed. OXD was found to be formed from DES by Fe2+/H2O2. No formation of IOXD was observed under the conditions of oxidation examined. By using a model compound of IDE, however, we found that 4-pyridone could be formed by Fe2+/H2O2. Elastin incubated in Cu2+/H2O2 was also solubilized dependent on solution pH and the concentration of H2O2. These results suggest that oxidative degradation of elastin with cross-links results in its weakening, followed by its solubilization. Pyridinium cross-links, such as DES and IDE, may be oxidatively metabolized by ROS, further changing to dihydrooxopyridine cross-links such as OXD and IOXD, respectively.

Topics: Animals; Aorta; Cattle; Chromatography, High Pressure Liquid; Cross-Linking Reagents; Desmosine; Elastin; Hydrogen Peroxide; Hydrogen-Ion Concentration; Magnetic Resonance Spectroscopy; Models, Chemical; Oxygen; Pyridines; Spectrophotometry; Time Factors; Ultraviolet Rays

2001