异奇沙宾二氢吡啶-C,N 合成及人皮肤中二氢吡啶和异二氢吡啶的定量 LC-MS/MS 分析。
IsoChichibabin desmosine-C,N synthesis and quantitative LC-MS/MS analysis of desmosine and isodesmosine in human skin.
机构信息
Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
Research Laboratories, KOSÉ Corporation, 48-18 Sakae-cho, Kita-ku, Tokyo 114-0005, Japan.
出版信息
Bioorg Med Chem. 2021 Dec 15;52:116519. doi: 10.1016/j.bmc.2021.116519. Epub 2021 Nov 20.
Desmosine and isodesmosine are crosslinking amino acids of elastin, which is an essential component of the dermal extracellular matrix protein. Quantitative analysis of crosslinker desmosines in human skin dermis has not been fully achieved due to the insoluble nature of elastin protein. In the present study, chemical synthesis of isotopically labeled desmosine, desmosine-C,N, was carried out via isoChichibabin pyridinium synthesis starting from corresponding isotopically labeled amino acids. Isotope-dilution LC-MS/MS analysis of desmosine and isodesmosine utilizing synthetic desmosine-C,N enabled the quantitative analysis of desmosines in human skin for the first time. Thus, ca. 1.43 μg of desmosines was detected from analysis of 1 mg of dry human skin.
赖氨酰正亮氨酸和异赖氨酰正亮氨酸是弹性蛋白的交联氨基酸，弹性蛋白是真皮细胞外基质蛋白的重要组成部分。由于弹性蛋白蛋白的不溶性，尚未完全实现对人皮肤真皮中交联剂赖氨酰正亮氨酸的定量分析。在本研究中，通过从相应的同位素标记氨基酸开始的异恰巴宾吡啶鎓合成，进行了同位素标记的赖氨酰正亮氨酸，即赖氨酰正亮氨酸-C,N 的化学合成。利用合成的赖氨酰正亮氨酸-C,N 进行的赖氨酰正亮氨酸和异赖氨酰正亮氨酸的同位素稀释 LC-MS/MS 分析，首次实现了人皮肤中赖氨酰正亮氨酸的定量分析。因此，从 1 毫克干燥的人皮肤分析中检测到约 1.43 微克的赖氨酰正亮氨酸。
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