Preparation of l-serine and l-cystine stereospecifically labeled with deuterium at the β-position |
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| Institution: | 1. Scientific Instrument Center, Shanxi University, Taiyuan, 030006, PR China;2. Department of Chemistry, Taiyuan Normal University, Taiyuan, 030031, PR China;3. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, PR China;1. Beijing National Laboratory for Molecular Sciences, Department of Polymer Science and Engineering and the Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Center for Soft Matter Science and Engineering, Peking University, Beijing 100871, PR China;2. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Renmin Street 5625, Changchun 130022, PR China;3. Key Laboratory of Functional Polymer Materials, Ministry of Education, College of Chemistry, Nankai University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, PR China;1. Moscow Chemical Lyceum, Tamozhenniy proezd 4, 111033 Moscow, Russia;2. Korea Science Academy of KAIST, 105-47, Baegyanggwanmun-ro, Busanjin-gu, 614-822 Busan, Republic of Korea;3. N.D. Zelinsky Institute of Organic Chemistry, Leninsky prospekt, 47, 119991 Moscow, Russia;4. A.N. Nesmeyanov Institute of Organic Chemistry, Vavilova St. 28, 119991 Moscow, Russia |
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| Abstract: | 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. |
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