Premium
Novel design and synthesis of a radioiodinated glycolipid analog as an acceptor substrate for N ‐acetylglucosaminyltransferase V
Author(s) -
Arimitsu Kenji,
Kimura Hiroyuki,
Kajimoto Tetsuya,
Ono Masahiro,
Ohmomo Yoshiro,
Yamashita Masayuki,
Node Manabu,
Saji Hideo
Publication year - 2013
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3063
Subject(s) - chemistry , glycolipid , stereochemistry , substrate (aquarium) , acetylation , alkyl , chemical synthesis , derivative (finance) , biochemistry , organic chemistry , in vitro , oceanography , economics , financial economics , gene , geology
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.