Description:
<jats:p>Guided by the known molecular recognition interactions between <jats:italic>N</jats:italic>‐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, [<jats:sup>125</jats:sup>I]‐2‐[<jats:italic>N</jats:italic>‐(2‐hydroxy‐3‐hexadecyloxy)propyl‐15‐(4‐iodophenyl)pentadecanecarboxamido]ethyl 2‐acetamido‐2‐deoxy‐β‐<jats:sc>d</jats:sc>‐glucopyranosyl‐(1→2)‐α‐<jats:sc>d</jats:sc>‐mannopyranosyl‐(1→6)‐β‐<jats:sc>d</jats:sc>‐glucopyranoside ([<jats:sup>125</jats:sup>I]2), as a novel intravital glycolipid mimic substrate of GnT‐V. The radioactive iodine (<jats:sup>125</jats:sup>I) was incorporated via iododestannylation of the phenyltributyltin derivative, 2‐[<jats:italic>N</jats:italic>‐(2‐acetoxy‐3‐hexadecyloxy)propyl‐15‐(4‐tributylstannylphenyl)pentadecanecarboxamido]ethyl 3,4,6‐tri‐<jats:italic>O</jats:italic>‐acetyl‐2‐acetamido‐2‐deoxy‐β‐<jats:sc>d</jats:sc>‐glucopyranosyl‐(1→2)‐3,4,6‐<jats:italic>O</jats:italic>‐acetyl‐α‐<jats:sc>d</jats:sc>‐mannopyranosyl‐(1→6)‐2,3,4‐tri‐<jats:italic>O</jats:italic>‐acetyl‐β‐<jats:sc>d</jats:sc>‐glucopyranoside (26). Subsequent deacetylation at the final step afforded [<jats:sup>125</jats:sup>I]2.</jats:p>