title: Novel design and synthesis of a radioiodinated glycolipid analog as an acceptor substrate for N-acetylglucosaminyltransferase V.
abstract: Guided by the known molecular recognition interactions between N-acetylglucosaminyltransferase V (GnT-V) and certain synthetic substrates, we synthesized a radiolabeled double-stranded glycolipid composed of a long-chain alkyl unit and a radioiodinated phenylalkyl unit, [(125)I]-2-[N-(2-hydroxy-3-hexadecyloxy)propyl-15-(4-iodophenyl)pentadecanecarboxamido]ethyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-β-D-glucopyranoside ([(125)I]2), as a novel intravital glycolipid mimic substrate of GnT-V. The radioactive iodine ((125)I) was incorporated via iododestannylation of the phenyltributyltin derivative, 2-[N-(2-acetoxy-3-hexadecyloxy)propyl-15-(4-tributylstannylphenyl)pentadecanecarboxamido]ethyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-O-acetyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside (26). Subsequent deacetylation at the final step afforded [(125)I]2.
authors.affiliation: Department of Patho-functional Bioanalysis, Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida Shimoadachi-cho, Sakyo-ku, Kyoto, 606-8501, Japan; Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, 1 Shichono-cho, Yamashina-ku, Kyoto, 607-8414, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Arimitsu
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kimura
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Kajimoto
authors.forename: Masahiro
authors.initials: M
authors.lastname: Ono
authors.forename: Yoshiro
authors.initials: Y
authors.lastname: Ohmomo
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yamashita
authors.forename: Manabu
authors.initials: M
authors.lastname: Node
authors.forename: Hideo
authors.initials: H
authors.lastname: Saji
mesh_terms: D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D007457:Iodine Radioisotopes / Q000737:chemistry; D008024:Ligands; D017351:N-Acetylglucosaminyltransferases / Q000378:metabolism*; D011485:Protein Binding; D011849:Radioactive Tracers
chemical_list: D006017:Glycolipids; D007457:Iodine Radioisotopes; D008024:Ligands; D011849:Radioactive Tracers; D007455:Iodine; D017351:N-Acetylglucosaminyltransferases; C052254:alpha-1,6-mannosylglycoprotein beta 1,6-N-acetylglucosaminyltransferase
keywords: N-acetylglucosaminyltransferase V (GnT-V); double-stranded lipid; radioiodinated glycolipid analog; trisaccharide