Total synthesis of COPD biomarker desmosine that crosslinks elastin.
نویسندگان
چکیده
Desmosine, a crosslinking amino acid of elastin, is an attractive biomarker for diagnosis of chronic obstructive pulmonary disease (COPD). In this study, the first total synthesis of (+)-desmosine was achieved in 11% overall yield in 13 steps utilizing stepwise and regioselective Sonogashira cross-coupling reactions.
منابع مشابه
Clinical validity of plasma and urinary desmosine as biomarkers for chronic obstructive pulmonary disease
BACKGROUND Although an increased concentration of degraded elastin products in patients with chronic obstructive pulmonary disease (COPD) has been reported for many years, its clinical validity and utility remain uncertain due to technical difficulties, small study groups and the unknown relationship between exacerbation and elastin degradation. The objectives of this study were to determine th...
متن کاملDesmosine as a biomarker of elastin degradation in COPD: current status and future directions.
Desmosine (DES) and isodesmosine (IDES) are two unusual, tetrafunctional, pyridinium ring-containing amino acids involved in elastin cross-linking. Being amino acids unique to mature, cross-linked elastin, they are useful for discriminating peptides derived from elastin breakdown from precursor elastin peptides. According to these features, DES and IDES have been extensively discussed as potent...
متن کاملSynthesis and LC-MS/MS analysis of desmosine-CH2, a potential internal standard for the degraded elastin biomarker desmosine.
Desmosine-CH2, an analog of the elastic tissue degradation biomarker desmosine, can be regarded as a potential internal standard for precise quantification of desmosines by LC-MS/MS. In this study, the chemical synthesis of desmosine-CH2 was completed in 22% overall yield in five steps. The LC-MS/MS analysis of desmosine-CH2 was also achieved.
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Correspondence chronic obstructive pulmonary disease . Am J Respir Crit Care Med . 1995 ; 151 ( 4 ): 952 959 . 3 . Cocci F , Miniati M , Monti S , et al . Urinary desmosine excretion is inversely correlated with the extent of emphysema in patients with chronic obstructive pulmonary disease . Int J Biochem Cell Biol . 2002 ; 34 ( 6 ): 594 604 . 4 . Albarbarawi O , Barton A , Lin Z , et al . Meas...
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Correspondence chronic obstructive pulmonary disease . Am J Respir Crit Care Med . 1995 ; 151 ( 4 ): 952 959 . 3 . Cocci F , Miniati M , Monti S , et al . Urinary desmosine excretion is inversely correlated with the extent of emphysema in patients with chronic obstructive pulmonary disease . Int J Biochem Cell Biol . 2002 ; 34 ( 6 ): 594 604 . 4 . Albarbarawi O , Barton A , Lin Z , et al . Meas...
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ورودعنوان ژورنال:
- Chemical communications
دوره 48 26 شماره
صفحات -
تاریخ انتشار 2012