Citation: OU Guang-Chuan, LI Zhi-Zhang, ZHANG Min, YUAN Xian-You. Chiral Resolution of β-dl-Phenylalanine Using Chiral Macrocyclic Nickel(Ⅱ) Complexes[J]. Chinese Journal of Structural Chemistry, ;2014, 33(5): 707-712. shu

Chiral Resolution of β-dl-Phenylalanine Using Chiral Macrocyclic Nickel(Ⅱ) Complexes

1.
Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China

Received Date: 29 October 2013
Available Online: 23 December 2013
Fund Project: Supported by the Scientific Research Fund of Hunan Provincial Education Department (13B029, 13A030, 13CY029) (13B029, 13A030, 13CY029) the Construct Program of the Key Discipline in Hunan Province (2011-76) (2013) and the Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province (2012-318) (2011-76)

The reactions of chiral four-coordinated nickel(Ⅱ) complex [Ni(RR-L)](ClO₄)₂/[Ni(SS-L)](ClO₄)₂ with β-dl-phenylalanine in acetonitrile/water gave a six-coordinated enantiomer of [Ni(RR-L)(β-d-HPhe)](ClO₄)₂ (1) and [Ni(SS-L)(β-l-HPhe)](ClO₄)₂ (2), respectively (L=5,5,7, 12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, HPhe=phenylalanine). Single-crystal X-ray diffraction analyses revealed that the nickel(Ⅱ) atom displays a distorted octahedral coordination geometry by coordinating with four nitrogen atoms of L in a folded configuration, and two carboxylate oxygen atoms of β-d/l-HPhe in cis-position in both complexes. The monomers of [Ni(RR-L)(β-d-HPhe)]²⁺ and [Ni(SS-L)(β-l-HPhe)]²⁺ are connected through intermolecular hydrogen bonds to generate one-dimensional zigzag chains, respectively. The homochiral natures of 1 and 2 are confirmed by the results of CD spectroscopy.
- chiral resolution,
- macrocyclic nickel(Ⅱ) complexes,
- β-dl-phenylalanine
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