Synthesis of Multi‐Deuterated Desmosine,ChemistrySelect

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Synthesis of Multi‐Deuterated Desmosine
ChemistrySelect ( IF 1.9 ) Pub Date : 2020-04-01 , DOI: 10.1002/slct.202000507
Mika Hirose ₁ , Reiko Yokoo ₁ , Daisuke Watanabe ₁ , Rina Suzuki ₁ , Miho Tanigawa ₁ , Toyonobu Usuki ₁

Affiliation

Desmosine, a crosslinking pyridinium amino acid found in elastin, is a useful biomarker for the diagnosis of diseases related to elastin degradation, such as chronic obstructive pulmonary disease (COPD). In order to achieve the precise quantitation of this compound using isotope dilution liquid chromatography‐tandem mass spectrometry (LC‐MS/MS) analysis, isotopically‐labeled internal standards including deuterated desmosine are required. We report herein the synthesis of multi‐deuterated desmosine (d_3–9) as a potential internal standard. This synthesis involves the preparation of an alkyne via a Sonogashira cross‐coupling, followed by deuterogenation of the triple bond to incorporate deuterium atoms into the substrate.

中文翻译：

多氘代地西敏的合成

Desmosine是一种在弹性蛋白中发现的交联吡啶鎓氨基酸，是诊断与弹性蛋白降解有关的疾病（例如慢性阻塞性肺疾病（COPD））的有用生物标记。为了使用同位素稀释液相色谱-串联质谱（LC-MS / MS）分析实现对这种化合物的精确定量，需要同位素标记的内部标准品，包括氘化的地高辛。我们在此报告了多氘代desmosine（d _3–9）的合成作为潜在的内标。该合成包括通过Sonogashira交叉偶联制备炔烃，然后对三键进行氘代化以将氘原子掺入底物中。

更新日期：2020-04-01

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