Syntheses of natural and deuterated desmosines via palladium-catalyzed cross-coupling reactions

被引：27
|
作者：
Suzuki, Rina [1 ]
Yanuma, Hiroto [1 ]
Hayashi, Takahiro [1 ]
Yamada, Haruka [1 ]
Usuki, Toyonobu [1 ]
机构：
[1] Sophia Univ, Fac Sci & Technol, Dept Mat & Life Sci, Chiyoda Ku, Tokyo 1028554, Japan
来源：
TETRAHEDRON | 2015年 / 71卷 / 12期
基金：
日本学术振兴会;
关键词：
Desmosine; Biomarker; Total synthesis; Sonogashira cross-coupling; Negishi cross-coupling; Deuterium; CHICHIBABIN PYRIDINE SYNTHESIS; OBSTRUCTIVE PULMONARY-DISEASE; TANDEM MASS-SPECTROMETRY; LINKING AMINO-ACIDS; LC-MS/MS ANALYSIS; HUMAN TROPOELASTIN; INTERNAL STANDARD; URINARY DESMOSINE; ELASTIN; ISODESMOSINE;
D O I：
10.1016/j.tet.2015.01.064
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Desmosine is a crosslinking pyridinium amino acid of elastin and is an attractive biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD). Herein, we describe the total synthesis of natural desmosine and its deuterated derivatives. The synthesized deuterated derivatives could be used as internal standards for the development of an isotope-dilution liquid chromatography-mass spectrometry (LC-MS/MS) analytical method for the accurate determination of desmosine in clinical samples. The key features of our synthesis are stepwise chemo- and regioselective palladium-catalyzed Sonogashira and Negishi cross-coupling reactions for the efficient introduction of the amino acid side chains onto the pyridine core. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1851 / 1862
页数：12
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