Chemical Synthesis of an Orthogonally Protected 5,7-Diamino-3,5,7,9-tetradeoxy-d-glycero-l-gluco-2-nonulosonic Acid from N -Acetylneuraminic Acid.

Autor: Ding M; Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China., Sun W; Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China., Tian G; Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China., Zou X; Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China., Hu J; Wuxi School of Medicine, Jiangnan University, Wuxi 214122, China., Qin C; Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China., Yin J; Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, School of Life Sciences and Health Engineering, Jiangnan University, Wuxi 214122, China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Jun 21; Vol. 26 (24), pp. 5215-5219. Date of Electronic Publication: 2024 Jun 11.
DOI: 10.1021/acs.orglett.4c01861
Abstrakt: Bacterial nonulosonic acids (NulOs), which feature a nine-carbon backbone, are associated with the biological functions of bacterial glycans. Here, an orthogonally protected 5-amino-7-azido-3,5,7,9-tetradeoxy-d-glycero-l-gluco-2-nonulosonic acid related to Fusobacterium nucleatum ATCC 23726 NulO was synthesized from N -acetylneuraminic acid with sequential performance of C5,7 azidation, C9 deoxygenation, C4 epimerization, and N5,7 differentiation. The C5 azido group in the obtained 5,7-diazido-NulO can be regioselectively reduced to differentiate the two amino groups.
Databáze: MEDLINE