ALTERNATIVE SYNTHESIS OF RADIOIODINATED TRISACCHARIDE DERIVATIVES, 2-(4-(IODOPHENY)-I-125)ETHYL 2-ACETAMIDO-2-DEOXY-beta-D-GLUCOPYRANOSYL-(1 -> 2)-alpha-D-MANNOPYRANOSYL-(1 -> 6)-beta-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

作者：Arimitsu Kenji^*; Kajimoto Tetsuya; Kimura Hiroyuki; Ono Masahiro; Ozeki Minoru; Node Manabu; Ohmomo Yoshiro; Saji Hideo; Yamashita Masayuki

来源：Heterocycles, 2011, 83(12): 2779-+.

DOI：10.3987/COM-11-12332

• Radioiodinated Trisaccharide Derivative
• N-Acetylglucosaminyltransferase V (GnT-V)
• Disaccharyl Sulfoxide
• Benzenethiol
• Glycosylation

A radioiodinated artificial substrate of N-acetylglucosaminyltransferase V (GnT-V), 2-(4-iodophenyl)ethyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 2)-alpha-D-mannopyranosyl-(1 -> 6)-beta-D-glucopyranoside (([I-125]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 [I-125]1a having different lengths of alkyl chain ([I-125]1b, [I-125]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-GIcNAc.

• 出版日期2011-12-1