Facile synthesis of mono-6-amino-6-deoxy-α-, β-, γ-cyclodextrin hydrochlorides for molecular recognition, chiral separation and drug delivery
Facile synthesis of mono-6-amino-6-deoxy-α-, β-, γ-cyclodextrin hydrochlorides for molecular recognition, chiral separation and drug delivery
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DOI：
10.1038/nprot.2008.37
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发表时间：
2008-01-01
期刊：
影响因子：
14.8
通讯作者：
Ng, Siu-Choon
中科院分区：
文献类型：
--
作者：
Tang, Weihua;Ng, Siu-Choon
我们描述了一种用于合成单-6-氨基-6-脱氧-环糊精盐酸盐（CD-NH3 Cl）的方案，其适用于α-、β-和γ-环糊精。这些结构最简单、水溶性高的阳离子环糊精可广泛应用于分子识别、手性分离和药物传递研究。从市售化学品开始，CD-NH3 Cl分四步合成：（i）通过使用对甲苯磺酰氯选择性地对环糊精进行甲苯磺酰化，得到单-6-甲基-N-苯基-N-甲基-N-苯基-N-甲基-N-苯基-N-甲基-N（ii）用叠氮化钠对Ts-CD进行叠氮取代，得到单-6-叠氮基-6-脱氧-环糊精（CD-N-3）;（iii）用三苯基膦还原CD-N-3，然后水解，制备单-6-氨基-6-脱氧-环糊精（CD-NH 2）;（iv）用盐酸处理CD-NH 2，以良好的产率得到标题CD-NH 3Cl。整个方案需要大约2周。
We describe a protocol for the synthesis of mono-6-amino-6-deoxy-cyclodextrin hydrochloride (CD-NH3Cl), applicable to alpha-, beta- and gamma-cyclodextrin. These structurally simplest, highly water-soluble cationic cyclodextrins can be widely used in molecular recognition, chiral separation and drug delivery studies. Starting from commercially available chemicals, CD-NH3Cl is synthesized in four steps: (i) selective tosylation of cyclodextrin by the use of p-toluenesulfonyl chloride to afford mono-6-(p-toluenesulfonyl)-6-deoxy-cyclodextrin(Ts-CD); (ii) azide substitution of Ts-CD with sodium azide to afford mono-6- azido-6-deoxy-cyclodextrin (CD-N-3); (iii) reduction of CD-N-3 with triphenylphospine followed by hydrolysis to prepare mono-6-amino-6-deoxy-cyclodextrin (CD-NH2); and (iv) treatment of CD-NH2 with hydrochloric acid to afford the titled CD-NH3Cl with good yield. The overall protocol requires similar to 2 weeks.