Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
Org Lett. 2012 Sep 21;14(18):4954-7. doi: 10.1021/ol3023227. Epub 2012 Sep 6.
The cell-surface glycans on bacteria contain many monosaccharides that cannot be obtained by isolation from natural sources. Availability of differentially protected monosaccharides is therefore often limiting access to potential oligosaccharide vaccine antigens. D-Fucosamine, D-bacillosamine, and D-xylo-2,6-deoxy-4-ketohexosamine building blocks were prepared via a divergent de novo synthesis from L-Garner aldehyde. The route relies on a chelation-control assisted organometallic addition and an anti-selective dihydroxylation reaction.
细菌表面的糖链含有许多单糖，这些单糖无法从天然来源中分离得到。因此，可用的、具有不同保护基团的单糖通常会限制潜在寡糖疫苗抗原的获得。D-岩藻糖胺、D-杆菌胺和 D-木糖-2,6-二脱氧-4-酮己糖胺砌块是通过从头合成 L-高纳尔醛制备的。该路线依赖于螯合控制辅助的有机金属加成和反选择性的二羟基化反应。
