Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose
Chitooligosaccharide with one 2,5-anhydro-d-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous acid depolymerization of chitosan. The reducing-end functionalization of COSamf by reductive amination with octanoic hydrazide in the presence of NaBH3CN was achieved in high yield. Th...
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| Format: | Article |
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MDPI AG
2016-08-01
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| Series: | Molbank |
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| Online Access: | http://www.mdpi.com/1422-8599/2016/3/M904 |
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| author | Amani Moussa Stéphane Trombotto |
| author_facet | Amani Moussa Stéphane Trombotto |
| author_sort | Amani Moussa |
| collection | DOAJ |
| description | Chitooligosaccharide with one 2,5-anhydro-d-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous acid depolymerization of chitosan. The reducing-end functionalization of COSamf by reductive amination with octanoic hydrazide in the presence of NaBH3CN was achieved in high yield. The chemical structure of the targeted octanoic hydrazide-linked COSamf was fully characterized by NMR spectroscopy and MALDI-TOF mass spectrometry. This synthesis opens the way to a new generation of COSamf derivatives with potential amphiphilic properties. |
| first_indexed | 2024-12-21T09:53:03Z |
| format | Article |
| id | doaj.art-00ec8a4f5adc488698e82673feb6db49 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-12-21T09:53:03Z |
| publishDate | 2016-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-00ec8a4f5adc488698e82673feb6db492022-12-21T19:08:08ZengMDPI AGMolbank1422-85992016-08-0120163M90410.3390/M904M904Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-MannofuranoseAmani Moussa0Stéphane Trombotto1Ingénierie des Matériaux Polymères (IMP, UMR CNRS 5223), Université Claude Bernard Lyon 1, Univ Lyon, Campus LyonTech-La Doua, bâtiment Polytech, 15 bd Latarjet, Villeurbanne F-69622, FranceIngénierie des Matériaux Polymères (IMP, UMR CNRS 5223), Université Claude Bernard Lyon 1, Univ Lyon, Campus LyonTech-La Doua, bâtiment Polytech, 15 bd Latarjet, Villeurbanne F-69622, FranceChitooligosaccharide with one 2,5-anhydro-d-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous acid depolymerization of chitosan. The reducing-end functionalization of COSamf by reductive amination with octanoic hydrazide in the presence of NaBH3CN was achieved in high yield. The chemical structure of the targeted octanoic hydrazide-linked COSamf was fully characterized by NMR spectroscopy and MALDI-TOF mass spectrometry. This synthesis opens the way to a new generation of COSamf derivatives with potential amphiphilic properties.http://www.mdpi.com/1422-8599/2016/3/M904chitosanchitooligosaccharide-2,5-anhydro-">d-mannofuranoseoctanoic hydrazidenitrous acid depolymerizationreductive amination, amphiphilic oligomer |
| spellingShingle | Amani Moussa Stéphane Trombotto Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose Molbank chitosan chitooligosaccharide-2,5-anhydro- ">d-mannofuranose octanoic hydrazide nitrous acid depolymerization reductive amination, amphiphilic oligomer |
| title | Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose |
| title_full | Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose |
| title_fullStr | Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose |
| title_full_unstemmed | Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose |
| title_short | Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose |
| title_sort | octanoic hydrazide linked chitooligosaccharides 2 5 anhydro d mannofuranose |
| topic | chitosan chitooligosaccharide-2,5-anhydro- ">d-mannofuranose octanoic hydrazide nitrous acid depolymerization reductive amination, amphiphilic oligomer |
| url | http://www.mdpi.com/1422-8599/2016/3/M904 |
| work_keys_str_mv | AT amanimoussa octanoichydrazidelinkedchitooligosaccharides25anhydrodmannofuranose AT stephanetrombotto octanoichydrazidelinkedchitooligosaccharides25anhydrodmannofuranose |