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Synlett 2000; 2000(6): 0797-0800
DOI: 10.1055/s-2000-6722
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Facile Solid Phase Synthesis of YEE(ah-GalNAc)3, a Ligand with Known High Affinity for the Asialoglycoprotein Receptor

Weir-Torn Jiaang* , Ping-Hui Tseng, Shui-Tein Chen
  • *Institute of Biological Chemistry, Academia Sinica, Taipei, 115, Taiwan; E-mail: bcchen@gate.sinica.edu.tw
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Publication Date:
31 December 2000 (online)

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A simple cluster glycoside, containing three residues of N-acetylgalactosamine with proper inter-residual distances, can be a high-affinity ligand for the asialoglycoprotein receptor (ASGPr) of mammalian liver. Tris(GalNAc-aminohexyl)glycoside of tyrosyl(glutamyl)glutamate YEE(ah-GalNAc)3 1, which is known to have sub-nanomolar affinity for the asialoglycoprotein receptor, was efficiently synthesized by using succinic acid as a linker to anchor GalNAc-aminohexyl glycoside to solid phase resin, followed by coupling the building blocks of Fmoc-(ah-α-GalNAcAc3)Glu and Fmoc-Tyr-OH to obtain YEE(ah-GalNAc)3 with a total yield of 83%.

asialoglycoprotein receptor - ligand - cluster glycoside - solid phase - oxazoline

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