Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong, P. R. China.
J Antibiot (Tokyo). 2019 Jun;72(6):420-431. doi: 10.1038/s41429-019-0170-3. Epub 2019 Mar 22.
Fusobacterium nucleatum is an oral bacteria related to various types of diseases. As Gram-negative bacteria, lipopolysaccharide (LPS) of Fusobacterium nucleatum could be a potential virulence factor. Recently, the structure of O-antigen in LPS of Fusobacterium nucleatum strain 25586 was elucidated to contain a trisaccharide repeating unit -(4-β-Nonp5Am-4-α-L-6dAltpNAc3PCho-3-β-D-QuipNAc)-. The nonulosonic acid characterized as 5-acetamidino-3,5,9-trideoxy-L-glycero-L-gluco-non-2-ulosonic acid (named as fusaminic acid), and 2-acetamido-2,6-dideoxy-L-altrose are the novel monosaccharides isolated. Herein we report the de novo synthesis of 5-N-acetyl fusaminic acid and the thioglycoside derivative in order to further investigate the biological significance of nonulosonic acids for bacterial pathogenesis.
具核梭杆菌是一种与多种疾病相关的口腔细菌。作为革兰氏阴性菌，具核梭杆菌的脂多糖（LPS）可能是一种潜在的毒力因子。最近，具核梭杆菌菌株 25586 的 LPS 中的 O-抗原结构被阐明，含有一个三糖重复单元-(4-β-Nonp5Am-4-α-L-6dAltpNAc3PCho-3-β-D-QuipNAc)-。所鉴定的非环单糖为 5-乙酰氨基-3,5,9-三脱氧-L-甘油-L-古洛糖-NON-2-酮基-2-尿苷酸（命名为 Fusaminic acid）和 2-乙酰氨基-2,6-二脱氧-L--altrose，是分离得到的新型单糖。在此，我们报告了 5-N-乙酰 Fusaminic acid 的从头合成以及硫糖苷衍生物，以进一步研究非环单糖在细菌发病机制中的生物学意义。
