Tn Antigen Mimics Based on sp2-Iminosugars with Affinity for an anti-MUC1 Antibody
详细信息 查看全文
- 作者：Elena M. Sánchez Fernández ; Claudio D. Navo ; Nuria Martínez-Sáez ; Rita Gonçalves-Pereira ; Víctor J. Somovilla ; Alberto Avenoza ; Jesús H. Busto ; Gonçalo J. L. Bernardes ; Gonzalo Jiménez-Osés ; Francisco Corzana ; José M. García Fernández ; Carmen Ortiz Mellet ; Jesús M. Peregrina
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：August 5, 2016
- 年：2016
- 卷：18
- 期：15
- 页码：3890-3893
- 全文大小：371K
- 年卷期：0
- ISSN：1523-7052
文摘
The first examples of amino acid (Ser/Thr)–sp2-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 sp2-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 sp2-iminosugar and the peptide aglycone structure (Ser/Thr).