Access to tetra-N-acetyl-chitopentaose by chemical N-acetylation of glucosamine pentamer.
作者： Maher Abla , Laurence Marmuse , Frédéric Delolme , Jean-Pierre Vors , Catherine Ladavière
DOI: 10.1016/J.CARBPOL.2013.06.078
关键词: Pentamer 、 Hydrochloride 、 Solvent 、 Chemistry 、 Glucosamine 、 Organic chemistry 、 Chemical synthesis 、 Yield (chemistry) 、 Selectivity 、 Deprotonation
摘要: Nowadays, the easy access of tetra-N-acetyl-chitopentaose and its counterparts is highly interesting since such chemical compounds are precursors biological signal molecules with a strong agro-economic impact. The synthesis by controlled N-acetylation glucosamine pentamer hydrochloride under mild conditions described herein. A systematic study on influence different parameters involved in this reaction, as solvent, acetylating agent, base used for deprotonation ammonium groups starting material was carried out. characterization final reaction products HPLC MALDI-TOF mass spectrometry showed that each these affects differently acetylation reaction. Whereas solvent plays an important role N- or O-acetylation selectivity, agent were found to both degree distribution partially N-acetylated derivatives product mixtures. Based results, optimized have been established allowing be synthesized one-pot deprotonation/N-acetylation moderate yield (ca 30%).
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