HETEROCYCLES

Paper | Regular issue | Vol. 83, No. 12, 2011, pp. 2779-2802
Received, 9th August, 2011, Accepted, 30th September, 2011, Published online, 13th October, 2011.
DOI: 10.3987/COM-11-12332

■ Alternative Synthesis of Radioiodinated Trisaccharide Derivatives, 2-(4-125Iodophenyl)ethyl 2-Acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-β-D-glucopyranoside, and Preparation of Its Analogs Having Different Lengths of Alkyl Chains Instead of Ethyl Group: Acceptor Substrates of N-Acetylglucosaminyltransferase V for in vivo Imaging

Kenji Arimitsu, Tetsuya Kajimoto, Hiroyuki Kimura, Masahiro Ono, Minoru Ozeki, Manabu Node, Yoshiro Ohmomo, Hideo Saji,* and Masayuki Yamashita*

Kyoto Pharmaceutical University, 5 Misasagi-Nakauchi, Yamashina, Kyoto, Japan

Abstract

A radioiodinated artificial substrate of N-acetylglucosaminyl- transferase V (GnT-V), 2-(4-iodophenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-β-D-glucopyranoside ([125I]1a), was alternatively synthesized by using the glycosylation reaction from the non-reducing end, in which a glycosyl sulfoxide and a thioglycoside were employed as the glycosyl acceptor and donor, respectively. In addition, two derivatives of [125I]1a having different lengths of alkyl chain ([125I]1b, [125I]1c) were prepared in the same way to increase the permeability of the substrates through the cell membrane and into the Golgi apparatus, where GnT-V acts to modify glycoconjugates by transferring N-acetylglucosamine units from UDP-GlcNAc.

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