Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide
Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide
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DOI：
10.1021/ja039374t
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发表时间：
2004-02-18
影响因子：
15
通讯作者：
Gin, MS
中科院分区：
文献类型：
--
作者：
Bodine, KD;Gin, DY;Gin, MS
报道了一种合成β-环糊精类似物的收敛策略，其利用叠氮基-炔三糖通过Cu（I）催化的炔和叠氮官能团的[3 + 2]偶极环加成的优先环二聚化。所得寡糖大环保留了环糊精的结合倾向，如对大环1和β-环糊精测量的类似ANS缔合常数所证明的。这种新的合成策略为模块化制备功能多样的环糊精类似物开辟了新的途径，否则无法获得。
A convergent strategy for the synthesis of β-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido−alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle1and β-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.