TY - JOUR
T1 - Tn Antigen Mimics Based on sp2-Iminosugars with Affinity for an anti-MUC1 Antibody
AU - Sánchez Fernández, Elena M
AU - Navo, Claudio D
AU - Martinez Saez, N.
AU - Conçalves-Pereira, Rita
AU - Somovilla Busto, V.J.
AU - Avenoza, Alberto
AU - Arenas Busto, Jesus
AU - Bernardes, Gonçalo J L
AU - Jiménez-Osés, Gonzalo
AU - Corzana, Francisco
AU - García Fernández, José M.
AU - Mellet, Carmen Ortiz
AU - Peregrina, Jesús M.
PY - 2016/8/5
Y1 - 2016/8/5
N2 - 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).
AB - 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).
U2 - 10.1021/acs.orglett.6b01899
DO - 10.1021/acs.orglett.6b01899
M3 - Article
SN - 1523-7060
VL - 18
JO - Organic Letters
JF - Organic Letters
IS - 15
ER -