Synthesis of l-(4-2H)erythrose,l-)1-13C, 5-2H)arabinose and l-(2-13C, 5-2H)arabinose and identification of the intermediates by 2H and 13C-N.M.R. spectroscopy |
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| Affiliation: | 1. Department of Biochemical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300350, PR China;2. Frontier Science Center for Synthetic Biology and Key Laboratory of Systems Bioengineering (MOE), Tianjin University, Tianjin, 300350, PR China;3. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin, 300350, PR China;4. Qingdao Institute for Marine Technology of Tianjin University, Qingdao, 266235, PR China;1. Department of Environmental Health, School of Public Health, Guangdong Provincial Key Laboratory of Tropical Disease Research, Southern Medical University, Guangzhou, Guangdong, China;2. State Key Laboratory of Organ Failure Research, Division of Laboratory Medicine, Zhujiang Hospital, Southern Medical University, Guangzhou, China;3. School of Traditional Chinese Medicine, Southern Medical University, Guangzhou, Guangdong, China;1. University of Vienna, Institute of Organic Chemistry, Währingerstrasse 38, A-1090 Vienna, Austria;2. Graz University of Technology, Institute of Biotechnology and Biochemical Engineering, Petersgasse 12/1, A-8010 Graz, Austria;1. School of Science, Guizhou Minzu University, Guiyang 550025, China;2. Collaborative Innovation Center of Biomass Energy, Henan Agricultural University, Zhengzhou 450002, Henan Province, China |
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| Abstract: | l-(1-13C, 5-2H)Arabinose (6D) and l-(2-13C, 5-2H)arabinose (8D) have been synthesized by degradation of 2,3-O-isopropylidene-α-l-rhamnofuranose (2) to l-(4-2H)erythrose (5β,5αD), with subsequent chain elongation to 6D plus l-(1-13C, 5-2H)ribose (7D), the latter being converted into 8D. Intermediates were identified by complete assignment of the 13C chemical shifts employing carbon-carbon and carbon-deuterium coupling constants, deuteration shifts, differential isotope-shifts, and deuterium spectra. The anomeric carbon atoms of 2 and 2,3-O-isopropylidene-l-(1-2H) erythrose (4D) gave only single 13C resonances, suggesting that these two compounds exists in only one major anomeric configuration, clarifying previously reported work. The synthesis of 2,3-O-isopropylidene-l-(1-2H)rhmanitol (3D) facilitated the assignment of the signals in the 13C spectra of the nondeuterated analog. Specific deuterium-enrichment and the observed carbon-deuterium coupling (1JC,D ∼22 Hz) not only served to identify the deuterated carbon atom unambiguously in 3 but also permitted assignment of closely spaced resonances. The deuterium spectrum of 2,3-O-isopropylidene-l-(1-2H)erythrofuranose (4D) showed only a single resonance, indicating preponderance of one anomer, in accord with the observation of a single C-1 resonance in the 13C spectrum. |
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