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Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: targeting the M6P/insulin-like growth factor II receptor.
- Source :
-
Organic letters [Org Lett] 2004 Dec 23; Vol. 6 (26), pp. 4921-4. - Publication Year :
- 2004
-
Abstract
- [reaction: see text] Mannose 6-phosphate mimics locked into the alpha-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.
Details
- Language :
- English
- ISSN :
- 1523-7060
- Volume :
- 6
- Issue :
- 26
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 15606100
- Full Text :
- https://doi.org/10.1021/ol0479444