ALPHA-SELECTIVE SIALYL DONORS AND ITS USES FOR PREPARATION OF SIALOSIDES

專利類型

發明

專利國別 (專利申請國家)

美國

專利申請案號

16/035,625

專利證號

US 10,435,425 B1

專利獲證名稱

ALPHA-SELECTIVE SIALYL DONORS AND ITS USES FOR PREPARATION OF SIALOSIDES

專利所屬機關 (申請機關)

中原大學

獲證日期

2019/10/08

技術說明

本揭示內容是關於一種唾液酸供體及其於合成神經節苷脂之用途。該唾液酸供體具有式(I)之結構，其中R1及R2分別為可以一鹵素任選取代的苯甲醯基、甲苯磺醯基、三甲基乙醯基或乙醯基；且R3是乙醯基或-(O)CCH2OH。在一較佳的實施方式中，於式(I)之唾液酸供體中，R是乙醯基。本揭示內容亦提供一種用以合成一唾液酸苷的方法。該方法包含：在具有N-碘琥珀醯亞胺及三氟甲磺酸之適合條件下，將式(I) 之唾液酸供體與一具有一級羥基之醣苷基受體耦合；以及單離該具有一α-醣苷鍵的唾液酸苷。依據較佳的實施方式，是於介於-20℃到-60℃的溫度中，在一選自CH3CN、CH3Cl及CH2Cl2所組成之群組的溶劑中進行耦合。此外或非必要性地，可於-40℃的溫度，在CH2Cl2中進行耦合。 Disclosed herein a sialyl donor and its use for the synthesis of gangliosides. The sialyl donor has the structure of, wherein, R1 and R2 are independently benzoyl, toluenesulfonyl, pivaloyl or acetyl optionally substituted with a hoalgen; and R3 is acetyl or -(O)CCH2OH. In one preferred embodiment, in the sialyl donor of formula (I), R is acetyl. Also disclosed herein is a method of synthesizing a sialoside. The method comprises steps of: coupling the sialyl donor of formua (I) with a glycosyl acceptor having a primary hydroxyl group in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) under suitable conditions; and isolating the sialoside, which has an α-glycosidic linkage. According to preferred embodiments, the coupling is conducted in a solvent selected from the group consisting of, CH3CN, CH3Cl, and CH2Cl2 at a temperature between -20℃ to -60℃. Additionaly or optionally, the coupling is conducted in CH2Cl2 with the presence of a powdered molecular sieve at -40℃.

備註

本會(收文號1110046848)同意該校111年7月21日原產字第1110002525號函申請終止維護專利(中原大學)

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