130931-83-8Relevant articles and documents
Optical resolution of 2-azabicyclo[2.2.1]hept-5-en-3-one by inclusion complexation with brucine
Tanaka, Koichi,Kato, Masako,Toda, Fumio
, p. 405 - 410 (2001)
A simple optical resolution method of 2-azabicyclo[2.2.1]hept-5-en-3-one by inclusion complexation with brucine was reported. The crystal structure of the inclusion complex was analyzed by X-Ray diffraction in order to elucidate the mechanism of the efficient chiral recognition in the inclusion crystals.
Green access to chiral Vince lactam in a buffer-free aqueous system using a newly identified substrate-tolerant (-)-γ-lactamase
Yin, Jin-Gang,Gong, Yi,Zhang, Xiao-Yan,Zheng, Gao-Wei,Xu, Jian-He
, p. 6305 - 6310 (2016)
A novel non-heme chloroperoxidase (SvGL) with promiscuous (-)-γ-lactamase activity towards Vince lactam was identified from Streptomyces viridochromogenes by genome data-mining. SvGL possesses high activity and excellent thermal stability and enantioselectivity. Furthermore, it is able to tolerate extremely high substrate concentrations (4.0 M, 436.5 g L-1). Using the newly discovered (-)-γ-lactamase as a biocatalyst, an efficient and environmentally benign process for the production of (+)-γ-lactam was developed. The process allowed an enantioselective resolution of 436.5 g L-1 racemic γ-lactam with only 0.2 g L-1 lyophilized cell-free extract, affording an extremely high substrate/catalyst ratio of 2183 (g g-1), a space-time yield of 458 g L-1 d-1, and a very low E factor (environmental factor) of 5.7 (kg waste per kg product) even when the process water is included.
Synthesis of rigid bicycloheterocyclic scaffolds from Vince's lactam (enzymatic resolution of Vince's lactam)
Gurjar, Mukund K.,Bera, Smritilekha,Joshi, Rohini R.,Joshi, Ramesh A.
, p. 2293 - 2303 (2003)
Vince's lactam, on oxidative cleavage and reduction, produced the 3,5-dihydroxymethylpyrrolidin-2-one derivative. This precursor has been utilized in intramolecular cyclization reactions to design some unique diaza-, oxaaza-, and thiaaza-bicyclic molecules as potential scaffolds in combinatorial chemistry.
Study on immobilization of (+) γ-lactamase using a new type of epoxy graphene oxide carrier
Li, Wei,Wen, Huijiao,Shi, Qianqiao,Zheng, Guojun
, p. 270 - 276 (2016/02/05)
In this article, a new type of graphene oxide material was obtained by modification with epoxy chloropropane, which was used for the (+) γ-lactamase immobilization research. The enzymatic properties of the immobilized (+) γ-lactamase were systematically tested and compared with those of the free enzyme. The free and immobilized enzymes have the same optimum temperature (80 °C) and pH (8.0), the range of pH tolerance increased from pH 8.0-9.0 to pH 4.0-10.0 after immobilization, and the immobilized enzyme is less tolerant to heat than the free enzyme. Kinetic experiments showed that the Km value of the immobilized enzyme was about 2.66 times higher than that of the free enzyme, whereas Vmax decreased 40%. Subsequently, the apparent activation energies (Ea) of the free and immobilized enzymes became 40.03 and 35.62 kJ/mol, respectively. Finally, a reusability assay demonstrated that 70% of the enzyme activity remained after 15 repeated batch experiments.