Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids

M. A. Khomutov; A. A. Formanovsky; I. V. Mikhura; J. Vepsalainen; S. N. Kochetkov; D. De Biase; A. R. Khomutov

doi:10.1134/S1068162016060042

Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids

作者: Khomutov M.A.¹, Formanovsky A.A.², Mikhura I.V.², Vepsalainen J.³, Kochetkov S.N.¹, De Biase D.⁴, Khomutov A.R.¹
隶属关系:
1. Engelhardt Institute of Molecular Biology
2. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry
3. School of Pharmacy
4. Istituto Pasteur Italia–Fondazione Cenci Bolognetti, Department of Medico-Surgical Sciences and Biotechnologies
期: 卷 42, 编号 6 (2016)
页面: 672-676
栏目: Article
URL: https://journal-vniispk.ru/1068-1620/article/view/228234
DOI: https://doi.org/10.1134/S1068162016060042
ID: 228234

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Three-steps, one-pot synthesis of 2-amino-4-(hydroxyphosphinyl)butyric acid from dibutyl ester of vinylphosphinic acid was carried out with an overall yield of 66%. 3-Aminopropylphosphinic acid was prepared from allylamine in three steps with an overall yield of 56%. These improved protocols allowed to obtain these commercially unavailable phosphinic analogues of glutamic acid and GABA for testing on potential molecular targets.