Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: Targeting the M6P/insulin-like growth factor II receptor

被引：44

作者：

Berkowitz, DB ^{[1
]}

Maiti, G

Charette, BD

Dreis, CD

MacDonald, RG

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

[2] Univ Nebraska, Med Ctr, Dept Biochem & Mol Biol, Omaha, NE 68198 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 26期

关键词：

D O I：

10.1021/ol0479444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：4921 / 4924

页数：4

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