| Publication Type |
Journal Article |
| Title |
Tn Antigen Mimics Based on sp(2)-Iminosugars with Affinity for an anti-MUC1 Antibody |
| Authors |
Elena M. Sanchez Fernandez Claudio D. Navo Nuria Martinez-Saez Rita Goncalves-Pereira Victor J. Somovilla Alberto Avenoza Jesus H. Busto Goncalo J. L. Bernardes Gonzalo Jimenez-Oses Francisco Corzana Jose M. Garcia Fernandez Carmen Ortiz Mellet Jesus M. Peregrina |
| Groups |
HC |
| Journal |
ORGANIC LETTERS |
| Year |
2016 |
| Month |
August |
| Volume |
18 |
| Number |
15 |
| Pages |
3890-3893 |
| Abstract |
The first, examples of amino acid (Ser/Thr)-sp(2)-iminosugar glycomimetic conjugates featuring an alpha-O-linked pseudoanomeric linkage are reported. The key synthetic step involves the completely diastereoselective alpha-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 (G1c/Gal/G1cNAc/Ga1NAc) of the sp(2)-iminosugar and the peptide aglycone structure (Ser/Thr). |
| DOI |
http://dx.doi.org/10.1021/acs.orglett.6b01899 |
| ISBN |
|
| Publisher |
|
| Book Title |
|
| ISSN |
1523-7060 |
| EISSN |
1523-7052 |
| Conference Name |
|
| Bibtex ID |
ISI:000381236300096 |
| Observations |
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