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ALTERNATIVE SYNTHESIS OF RADIOIODINATED TRISACCHARIDE DERIVATIVES, 2-(4-(125)IODOPHENY)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  
  选自 期刊  Heterocycles;  卷期  2011年83-12;  页码  2779-+  
  关联知识点  
 

[摘要]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 (([(125)I]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 [(125)I]1a having different lengths of alkyl chain ([(125)I]1b, [(125)I]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.

 
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