Construct of drug delivery system using carbohydrate recognition

1.6 ^ 1的制备和表征,6 ^ 2 - 6 ^ 1,6 ^ 3 - 6 ^ 1,6 ^ 4-Di-O -(α-L-fucopyranosyl) -β-环糊精和FunctionsThree位置异构体的研究6 ^ 1,6 ^ n-di-O -(α-L-fucopyranosyl) -βCDs [6 ^ 1 6 ^ n-di-O -(α-L-Fuc) -βcd, n = 2 - 4)被使用真实的化合物,化学合成6 ^ 1,6 ^ n-di-O - (tert-butyldimethylsilyl)βcd (n = 2 - 4)作为focusyl中间体,focusyl捐赠者,2,3,4-tri-O-acetyl-L-fucopyranosyl trichloroacetimidate。采用HPLC、MS和NMR对其结构进行了分析。利用光学生物传感器研究了这些化合物与聚焦结合凝集素AAL （Aleuria aurantia凝集素）的特异性相互作用。结合亲和力为6^1,6^4- > 6^1,6^3- > 6^1,6^2-di-O-(α-L-Fuc)-β cd > 6- o -(α-L-Fuc)-β cd。以β- d - n -乙酰氨基葡萄糖-麦芽糖糖为侧链的新型杂支β-环糊精的合成cNAc-βCD，半乳糖- n -乙酰氨基葡萄糖-βCD；GlcNAc-Glc_3-βCD， n -乙酰氨基葡萄糖-麦芽糖三酰-βCD；Gal-GlcNAc-Glc_3 -βCD, galactosyl-Nacetylglucosaminyl-maltotriosyl -βCD。以n -乙酰氨基葡萄糖-β-环糊精（GlcNAc-βCD）和乳糖为原料，通过β-半乳糖苷酶的转移作用合成了β- d -半乳糖-GlcNAc-βCD （Gal-GlcNAc-βCD）。用环糊精糖基转移酶水解GlcNAc-βCD，用细菌糖化α-淀粉酶水解Gal-GlcNAc-βCD，分别制得GlcNAc-麦芽糖（Glc_3）和Gal-GlcNAc-Glc_3。最后，将GlcNAc-Glc_3-βCD或Gal-GlcNAc-Glc_3-βCD与肺炎克雷伯菌普卢聚糖酶混合培养，分别以5.2%和3.5%的产率合成GlcNAc-Glc_3-βCD和Gal-GlcNAc-Glc_3-βCD。采用FAB-MS和NMR对glcnac - glcac - glc_3 -βCD和Gal-GlcNAc-Glc_3-βCD的结构进行了分析，鉴定为6- o- α-（6^3-O-β- d - n -乙酰氨基葡萄糖-麦芽-三酰基）-βCD和6- o- α-（4-O-β- d - n -乙酰氨基葡萄糖-麦芽-三酰基）-βCD。少

1.Preparation and Characterization of 6^1,6^2-,6^1,6^3-, and 6^1,6^4-Di-O-(α-L-fucopyranosyl)-β- cyclodextrins and Study of Their FunctionsThree positional isomers of 6^1,6^n-di-O-(α-L-fucopyranosyl)-βCDs [6^1,6^n-di-O- (α-L-Fuc)-βCDs, n=2-4] were chemically synthesized by using the authentic compounds, 6^1,6^n-di-O-(tert-butyldimethylsilyl)-βCDs (n=2-4) as the fucosyl intermediates, and the fucosyl donor, 2,3,4-tri-O-acetyl-L-fucopyranosyl trichloroacetimidate. Their structures were analyzed by HPLC, MS, and NMR spectroscopy. The specific interaction between those compounds and fucose-binding lectin AAL (Aleuria aurantia lectin) were investigated by using an optical biosensor. The binding affinity was 6^1,6^4- > 6^1,6^3- > 6^1,6^2-di-O-(α-L-Fuc)-βCD > 6-O-(α-L- Fuc)-βCD in the comparison by the fucose-binding position.2.Synthesis of Novel Heterobranched β-Cyclodextrins Having β-D-N-Acetylglucosaminyl-Maltotriose on the Side ChainGlcNAc-βCD, N-acetylglucosaminyl-β-cyclodextrin ; Gal-Gl … More cNAc-βCD, galactosyl-N-acetyl-glucosaminyl-βCD ; GlcNAc-Glc_3-βCD, N-acetylglucosaminyl-maltotriosyl-βCD ; Gal-GlcNAc-Glc_3-βCD, galactosyl-Nacetylglucosaminyl-maltotriosyl-βCD. From a mixture of N-acetylglucosaminyl-β-cyclodextrin (GlcNAc-βCD) and lactose, β-D-galactosyl-GlcNAc-βCD (Gal-GlcNAc-βCD) was synthesized by the transfer action of β-galactosidase. GlcNAc-maltotriose (Glc_3) and Gal-GlcNAc-Glc_3 were produced with hydrolysis of GlcNAc-βCD by cyclodextrin glycosyltransferase, and Gal-GlcNAc-βCD by bacterial saccharifying α-amylase respectively. Finally, GlcNAc-Glc_3-βCD and Gal-GlcNAc-Glc_3-βCD were synthesized in 5.2% and 3.5% yield when Klebsiella pneumoniae pullulanase was incubated with the mixture of GlcNAc-Glcs and βCD, or Gal-GlcNAc-Glc_3 and βCD respectively. The structures of GlcNAc-Glc_3-βCD and Gal-GlcNAc-Glc_3-βCD were analyzed by FAB-MS and NMR spectroscopy and identified as 6-O-α-(6^3-O-β-D-N-acetylglucosaminyl-malto- triosyl)- βCD, and 6-O-α-(4-O-β-D-galactopyranosyl-6^3-O-β-D-N-acetylglucosaminyl-maltotriosyl)-βCD respectively. Less