Preparation of l-serine and l-cystine stereospecifically labeled with deuterium at the β-position

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• 作者：Makoto Oba ; Akira Iwasaki ; Hiroshi Hitokawa ; Toshinori Ikegame ; Hiroyuki Banba ; Kozo Ura ; Tadashi Takamura and Kozaburo Nishiyama
• 刊名：Tetrahedron: Asymmetry
• 出版年：2006
• 出版时间：31 July 2006
• 年：2006
• 卷：17
• 期：12
• 页码：1890-1894
• 全文大小：140 K

文摘

The synthesis of l-serine and l-cystine stereospecifically labeled with deuterium at the β-position is described. The carboxyl group of d-serine was transformed into chirally deuterium-labeled alcohol via asymmetric reduction of 1-deuterio aldehyde, while the original hydroxymethyl group was converted into a carboxyl functionality to afford (2S,3R)-[3-²H]serine. Functional group interconversions of the hydroxyl group in the obtained deuterium-labeled l-serine gave (2R,2′R,3S,3′S)-[3,3′-²H₂]cystine.