Synthesis
Synthesis of mono-(6-amino-6-deoxy)-β-cyclodextrin (CDNH2): 30 mL of an aqueous ammonia solution was added to 3 g of crude mono-6-O-(p-toluenesulfonyl)-β-cyclodextrin (CDOT) and the reaction mixture was stirred for 72 h at 50 °C. The reaction was carried out in a cold acetone solution. Upon completion of the reaction, the solution was recrystallized in cold acetone to give the crude product CDNH2. This crude product was subsequently purified by a cation exchange column, sequentially using deionized water and 0.1 M (NH4)2CO3 buffered aqueous solution as eluents. The total yield of the purified product was 79%. The reaction process and product purity were monitored by thin-layer chromatography (TLC) with the unfolding agent ratio of 1-propanol:ethyl acetate:water:NH3-H2O = 3:1:2:1 (v/v) and color development using CAM solution.
References
[1] Tetrahedron Letters, 2010, vol. 51, # 5, p. 800 - 803
[2] Patent: WO2016/126910, 2016, A1. Location in patent: Page/Page column 29
[3] Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2012, vol. 73, # 1-4, p. 475 - 478
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3346 - 3348
[5] Angewandte Chemie - International Edition, 2015, vol. 54, # 41, p. 12127 - 12133
