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Total Synthesis of a Conjugation-Ready Tetrasaccharide Repeating Unit of Vibrio cholerae O:3 O-antigen Polysaccharide
Organic Letters ( IF 4.9 ) Pub Date : 2024-01-10 , DOI: 10.1021/acs.orglett.3c04225 Soumyakanta Maji 1 , Balasaheb K Ghotekar 1 , Suvarn S Kulkarni 1
Organic Letters ( IF 4.9 ) Pub Date : 2024-01-10 , DOI: 10.1021/acs.orglett.3c04225 Soumyakanta Maji 1 , Balasaheb K Ghotekar 1 , Suvarn S Kulkarni 1
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Herein, we report the first total synthesis of the tetrasaccharide repeating unit of Vibrio cholerae O:3 O-antigen polysaccharide. The highly complex tetrasaccharide contains rare amino sugars such as d-bacillosamine and l-fucosamine, highly labile sugar ascarylose, and higher carbon sugar d-d-heptose. Stereoselective glycosylation of the notoriously reactive ascarylose with d-d-heptose, poor nucleophilicity of the axial C4-OH of l-fucosamine, and amide coupling are the key challenges encountered in the total synthesis, which was completed via a longest linear sequence of 23 steps in 4.2% overall yield.
中文翻译：
霍乱弧菌 O:3 O-抗原多糖的可缀合四糖重复单元的全合成
在此，我们报道了霍乱弧菌O:3 O-抗原多糖四糖重复单元的首次全合成。高度复杂的四糖含有稀有氨基糖，如d-芽孢杆菌胺和l-岩藻糖胺、高度不稳定的糖蛔糖和高碳糖d - d-庚糖。臭名昭著的活性蛔糖与d - d-庚糖的立体选择性糖基化、 l-岩藻糖胺的轴向C4-OH亲核性差以及酰胺偶联是全合成中遇到的关键挑战，该合成是通过最长的23线性序列完成的总收益率达到 4.2%。
更新日期：2024-01-10
中文翻译：
霍乱弧菌 O:3 O-抗原多糖的可缀合四糖重复单元的全合成
在此，我们报道了霍乱弧菌O:3 O-抗原多糖四糖重复单元的首次全合成。高度复杂的四糖含有稀有氨基糖，如d-芽孢杆菌胺和l-岩藻糖胺、高度不稳定的糖蛔糖和高碳糖d - d-庚糖。臭名昭著的活性蛔糖与d - d-庚糖的立体选择性糖基化、 l-岩藻糖胺的轴向C4-OH亲核性差以及酰胺偶联是全合成中遇到的关键挑战，该合成是通过最长的23线性序列完成的总收益率达到 4.2%。
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