Tang Weihua, Ng Siu-Choon
Department of Chemistry, National University of Singapore, Singapore 117543, Singapore.
Nat Protoc. 2008;3(4):691-7. doi: 10.1038/nprot.2008.37.
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-N3); (iii) reduction of CD-N3 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 approximately 2 weeks.
我们描述了一种适用于α-、β-和γ-环糊精的单-6-氨基-6-脱氧环糊精盐酸盐（CD-NH₃Cl）的合成方案。这些结构最简单、高度水溶性的阳离子环糊精可广泛用于分子识别、手性分离和药物递送研究。以市售化学品为起始原料，CD-NH₃Cl通过四个步骤合成：（i）使用对甲苯磺酰氯对环糊精进行选择性甲苯磺酰化，得到单-6-（对甲苯磺酰基）-6-脱氧环糊精（Ts-CD）；（ii）用叠氮化钠对Ts-CD进行叠氮基取代，得到单-6-叠氮基-6-脱氧环糊精（CD-N₃）；（iii）用三苯基膦还原CD-N₃，然后水解制备单-6-氨基-6-脱氧环糊精（CD-NH₂）；（iv）用盐酸处理CD-NH₂，以良好的产率得到标题化合物CD-NH₃Cl。整个方案大约需要2周时间。
