Access to tetra-N-acetyl-chitopentaose by chemical N-acetylation of glucosamine pentamer - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Carbohydrate Polymers Année : 2013

Access to tetra-N-acetyl-chitopentaose by chemical N-acetylation of glucosamine pentamer

Résumé

Nowadays, the easy access of tetra-N-acetyl-chitopentaose and its counterparts is highly interesting since such chemical compounds are precursors of biological signal molecules with a strong agro-economic impact. The chemical synthesis of tetra-N-acetyl-chitopentaose by controlled N-acetylation of the glucosamine pentamer hydrochloride under mild conditions is described herein. A systematic study on the influence of the different parameters involved in this reaction, such as the solvent, the acetylating agent, and the base used for the deprotonation of ammonium groups of the starting material was carried out. The characterization of final reaction products by HPLC and MALDI-TOF mass spectrometry showed that each of these parameters affects differently the acetylation reaction. Whereas the solvent plays an important role in the N- or O-acetylation selectivity, the acetylating agent and the base were found to influence both the degree of N-acetylation and the distribution of the partially N-acetylated derivatives in the product mixtures. Based on these results, optimized reaction conditions have been established allowing tetra-N-acetyl-chitopentaose to be synthesized in a one-pot deprotonation/N-acetylation of the glucosamine pentamer hydrochloride in a moderate yield (ca 30%).

Dates et versions

hal-00869815 , version 1 (04-10-2013)

Identifiants

Citer

Maher Abla, Laurence Marmuse, Frédéric Delolme, Jean-Pierre Vors, Catherine Ladavière, et al.. Access to tetra-N-acetyl-chitopentaose by chemical N-acetylation of glucosamine pentamer. Carbohydrate Polymers, 2013, 98, pp.770-777. ⟨10.1016/j.carbpol.2013.06.078⟩. ⟨hal-00869815⟩
105 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More