Tn Antigen Mimics Based on sp(2)-Iminosugars with Affinity for an anti-MUC1 Antibody.
Tn Antigen Mimics Based on sp(2)-Iminosugars with Affinity for an anti-MUC1 Antibody.
复制标题
基于 sp(2)-亚氨基糖的 Tn 抗原模拟物，具有抗 MUC1 抗体的亲和力。
作者：
E. Fernández;Claudio D. Navo;N. Martínez;R. Gonçalves;V. J. Somovilla;A. Avenoza;J. H. Busto;G. Bernardes;Gonzalo Jiménez‐Osés;F. Corzana;J. M. Fernández;C. Mellet;J. M. Peregrina
报道了第一个具有α-O-连接的假异头键的氨基酸（Ser/Thr）-sp（2）-亚氨基糖糖模拟物缀合物的实例。关键的合成步骤涉及Ser/Thr的完全非对映选择性α-糖基化，这是由于双环sp（2）-亚氨基糖支架施加的强立体电子和构象偏好。包含这些基序的粘蛋白相关糖肽被单克隆抗体（mAb）scFv-SM 3识别，其活性取决于sp（2）-亚氨基糖的羟基化模式（Glc/Gal/GlcNAc/GalNAc）和肽糖苷配基结构（Ser/Thr）。
The first examples of amino acid (Ser/Thr)-sp(2)-iminosugar glycomimetic conjugates featuring an α-O-linked pseudoanomeric linkage are reported. The key synthetic step involves the completely diastereoselective α-glycosylation of Ser/Thr due to strong stereoelectronic and conformational bias imposed by the bicyclic sp(2)-iminosugar scaffold. Mucin-related glycopeptides incorporating these motifs were recognized by the monoclonal antibody (mAb) scFv-SM3, with activities depending on both the hydroxylation pattern (Glc/Gal/GlcNAc/GalNAc) of the sp(2)-iminosugar and the peptide aglycone structure (Ser/Thr).
DOI：
10.1002/anie.201406897
发表时间：
2014-10-27
期刊：
Angewandte Chemie (International ed. in English)
影响因子：
--
作者：
Richichi B;Thomas B;Fiore M;Bosco R;Qureshi H;Nativi C;Renaudet O;BenMohamed L
通讯作者：
BenMohamed L
影响因子：
4.3
作者：
Kinarsky, L;Suryanarayanan, G;Sherman, S
通讯作者：
Sherman, S
影响因子：
15
作者：
Coltart, DM;Royyuru, AK;Live, DH
通讯作者：
Live, DH