Novel design and synthesis of a radioiodinated glycolipid analog as an acceptor substrate for N‐acetylglucosaminyltransferase V. (4th September 2013)

• Record Type: Journal Article
• Authors: Arimitsu, Kenji; Kimura, Hiroyuki; Kajimoto, Tetsuya; Ono, Masahiro; Ohmomo, Yoshiro; Yamashita, Masayuki; Node, Manabu; Saji, Hideo
• Is Part Of: Journal of labelled compounds & radiopharmaceuticals. Volume 56:Number 11(2013)
• Page Start: 562
• Page End: 572
• Publication Date: 2013-09-04
• Subjects: Tracers (Chemistry) -- Periodicals; Radiopharmaceuticals -- Periodicals; 615.8424
• DOI: 10.1002/jlcr.3063
• Languages: English
• ISSNs: 0362-4803

Abstract

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