NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution
The products of the reaction of d-glucuronic acid with various combinations of ammonia and volatile ammonium salts in water were studied by NMR and MS spectroscopy. For long reaction times (~24 h), the expected products β-d-glucopyranosylamine uronic acid and ammonium N-(β-d-glucopyranosyluronic aci...
| Main Authors: | , , , , |
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| Format: | Journal Article |
| Language: | English |
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2014
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| Online Access: | https://hdl.handle.net/10356/99944 http://hdl.handle.net/10220/19536 |
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| author | Ghadban, Ali Albertin, Luca Condamine, Eric Mounguengui, Rédéo W. Moussavou Heyraud, Alain |
| author2 | School of Materials Science & Engineering |
| author_facet | School of Materials Science & Engineering Ghadban, Ali Albertin, Luca Condamine, Eric Mounguengui, Rédéo W. Moussavou Heyraud, Alain |
| author_sort | Ghadban, Ali |
| collection | NTU |
| description | The products of the reaction of d-glucuronic acid with various combinations of ammonia and volatile ammonium salts in water were studied by NMR and MS spectroscopy. For long reaction times (~24 h), the expected products β-d-glucopyranosylamine uronic acid and ammonium N-(β-d-glucopyranosyluronic acid)carbamate were obtained in good-to-high yield, whereas seven intermediate species were identified in samples taken at earlier reaction times. 1H–1H homonuclear and 1H–13C heteronuclear correlation experiments enabled a complete assignment of the 1H and 13C NMR spectra of the starting and final compounds, and a partial assignment of the peaks of intermediate species. Based on these results, a 1H NMR protocol for the quantification of the different compounds taking part in the reaction was developed, which was used to monitor the evolution of the composition of an early reaction sample redissolved in D2O. It was thus established that two of the observed intermediate species are actually the α anomer of the main products, whereas the others are precursors to the formation of α/β-d-glucopyranosylamine uronic acid and ammonium N-(α/β-d-glucopyranosyluronic acid)carbamate. The correct assignments for the 1H and 13C spectra of d-glucuronic acid in D2O are also reported. |
| first_indexed | 2024-10-01T03:48:19Z |
| format | Journal Article |
| id | ntu-10356/99944 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:48:19Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/999442020-06-01T10:21:11Z NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution Ghadban, Ali Albertin, Luca Condamine, Eric Mounguengui, Rédéo W. Moussavou Heyraud, Alain School of Materials Science & Engineering DRNTU::Science::Chemistry The products of the reaction of d-glucuronic acid with various combinations of ammonia and volatile ammonium salts in water were studied by NMR and MS spectroscopy. For long reaction times (~24 h), the expected products β-d-glucopyranosylamine uronic acid and ammonium N-(β-d-glucopyranosyluronic acid)carbamate were obtained in good-to-high yield, whereas seven intermediate species were identified in samples taken at earlier reaction times. 1H–1H homonuclear and 1H–13C heteronuclear correlation experiments enabled a complete assignment of the 1H and 13C NMR spectra of the starting and final compounds, and a partial assignment of the peaks of intermediate species. Based on these results, a 1H NMR protocol for the quantification of the different compounds taking part in the reaction was developed, which was used to monitor the evolution of the composition of an early reaction sample redissolved in D2O. It was thus established that two of the observed intermediate species are actually the α anomer of the main products, whereas the others are precursors to the formation of α/β-d-glucopyranosylamine uronic acid and ammonium N-(α/β-d-glucopyranosyluronic acid)carbamate. The correct assignments for the 1H and 13C spectra of d-glucuronic acid in D2O are also reported. 2014-06-04T01:51:25Z 2019-12-06T20:13:52Z 2014-06-04T01:51:25Z 2019-12-06T20:13:52Z 2011 2011 Journal Article Ghadban, A., Albertin, L., Condamine, E., Mounguengui, R. W. M. & Heyraud, A. 2011. NMR and MS study of the formation of β-d-glucopyranosylamine uronic acid in aqueous solution. Canadian Journal of Chemistry, 89(8), 987 - 1000. https://hdl.handle.net/10356/99944 http://hdl.handle.net/10220/19536 10.1139/V11-064 en Canadian journal of chemistry © 2011 NRC Research Press. |
| spellingShingle | DRNTU::Science::Chemistry Ghadban, Ali Albertin, Luca Condamine, Eric Mounguengui, Rédéo W. Moussavou Heyraud, Alain NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution |
| title | NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution |
| title_full | NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution |
| title_fullStr | NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution |
| title_full_unstemmed | NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution |
| title_short | NMR and MS study of the formation of β-D-glucopyranosylamine uronic acid in aqueous solution |
| title_sort | nmr and ms study of the formation of β d glucopyranosylamine uronic acid in aqueous solution |
| topic | DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/99944 http://hdl.handle.net/10220/19536 |
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