Takeda Ryosuke, Abe Hidenori, Shibata Norio, Moriwaki Hiroki, Izawa Kunisuke, Soloshonok Vadim A
Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan.
Org Biomol Chem. 2017 Aug 23;15(33):6978-6983. doi: 10.1039/c7ob01720k.
α-Deuterated-α-amino acids represent a very special class of stable isotopically labeled compounds, used in advanced biomedical research. Herein, we disclose a generalized approach for the preparation of α-H-α-amino acids in enantiomerically pure form and with up to 99% deuteration. The reaction chemistry involved in this process is based on the dynamic kinetic resolution of racemates or (S)-(R) interconversion via the formation of intermediate Ni(ii) complexes derived from unprotected amino acids and recyclable tridentate ligands. Operationally convenient conditions, excellent chemical yields, diastereoselectivity and the degree of the deuteration bode well for the wide application of this methodology for the preparation of tailor-made α-H-α-amino acids.
α-氘代-α-氨基酸是一类非常特殊的稳定同位素标记化合物，用于先进的生物医学研究。在此，我们公开了一种通用方法，用于制备对映体纯形式且氘代率高达99%的α-H-α-氨基酸。该过程涉及的反应化学基于外消旋体的动态动力学拆分或通过由未保护氨基酸和可循环使用的三齿配体形成的中间体Ni(ii)配合物进行的(S)-(R)互变。操作简便的条件、优异的化学产率、非对映选择性和氘代程度预示着该方法在制备定制的α-H-α-氨基酸方面具有广泛的应用前景。
