Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams? |
| |
| Institution: | 1. Metabolic Diseases Chemistry, Bristol-Myers Squibb Research and Development, Princeton, NJ 08543-5400, United States;2. BMS-Biocon Research Center, Biocon, 20th KM, Hosur Road, Electronic City, Bangalore 560 100, India;3. Metabolic Diseases Biology, Bristol-Myers Squibb Research and Development, Princeton, NJ 08543-5400, United States;4. Pharmaceutical Candidate Optimization, Bristol-Myers Squibb Research and Development, Princeton, NJ 08543-5400, United States;1. Laboratory of Cell Biology, Wageningen University, Droevendaalsesteeg 1, 6708 PB Wageningen, the Netherlands;2. Marine Biological Laboratory, 7 MBL Street, Woods Hole, MA 02543, USA;3. Division of Biological Science, Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8602, Japan;1. School of Biological Science and Technology, University of Jinan, Jinan 250022, PR China;2. Key Laboratory of TCM Quality Control Technology, Shandong Analysis and Test Center, Jinan 250014, PR China;3. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin 541004, PR China;1. Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., Osaka, Japan;2. Genomic Science Laboratories, Dainippon Sumitomo Pharma Co., Ltd., Osaka, Japan;1. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10 Jankipuram Extension, Sitapur Road, Lucknow 226031, India;2. Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India |
| |
| Abstract: | Twelve-membered cyclic cis- and trans-β-lactams 1b and 2b and the corresponding cyclic cis- and trans-β-amino acid enantiomers, 1a, 1c and 2a, 2c were prepared through the CAL-B-catalysed enantioselective ring cleavage of racemic cis-13-azabicyclo10.2.0]tetradecan-14-one, (±)-1, and trans-13-azabicyclo10.2.0]tetradecan-14-one, (±)-2. High enantioselectivities (E >200) were observed for the ring opening of both the cis- and trans-β-lactams when the Lipolase-catalysed reactions were performed with 0.5 equiv of H2O in i-Pr2O at 70 °C. The resolved β-lactams 1b and 2b (yield ⩾47%) and β-amino acids 1a and 2a (yield ⩾32%) could be easily separated. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
