Sunkari Yashoda Krishna, Alam Faiyaz, Kandiyal Pancham Singh, Aloysius Siriwardena, Ampapathi Ravi Sankar, Chakraborty Tushar Kanti
Department of Organic Chemistry, Indian Institute of Science, CV Raman Road, Bengaluru, 560012, India.
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow, 226031, India.
Chembiochem. 2016 Oct 4;17(19):1839-1844. doi: 10.1002/cbic.201600386. Epub 2016 Aug 18.
Glycosylation of foldamers derived from furanoid sugar amino acids with mannose and a propyltriazole linker results in an unprecedented 16/10 mixed-turn structure in the glycopeptides in water, with a preference for the higher-order structure irrespective of the stereochemistry of the starting foldamer. This is in stark contrast to the structures displayed by the same oligomers in water when mannosylated with a two-carbon-shorter methyltriazole linker: 16-membered turn structure in the cis-foldamer and 10-membered in its trans congener. This demonstrates the defining influence of the linker length on the structural preference of these novel glycopeptide mimics.
由呋喃糖氨基酸衍生而来的折叠体与甘露糖及丙基三唑连接基进行糖基化反应，在水中的糖肽中形成了前所未有的16/10混合转角结构，无论起始折叠体的立体化学如何，都倾向于形成高阶结构。这与用短两个碳原子的甲基三唑连接基进行甘露糖基化时，相同低聚物在水中所呈现的结构形成鲜明对比：顺式折叠体中为16元转角结构，其反式异构体中为10元转角结构。这证明了连接基长度对这些新型糖肽模拟物结构偏好的决定性影响。
