Synthesis of the 3'-C-carboxymethyl Lewis X derivative: A novel selectin blocker

Hideharu Ishida, Hiroyuki Hosokawa, Hirosato Kondo, Makoto Kiso, Akira Hasegawa

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The 3'-C-carboxymethyl Le(x) derivative carrying the 2-(tetradecyl)hexadecyl residue was synthesized by employing 3'-C-carboxymethyl galactose as a key intermediate, which was prepared from the suitably protected galactose by Swern oxidation and Wittig-Horner carboxymethylenation, followed by stereoselective reduction of the double bond. The compound obtained showed much more potent activity as a selectin blocker than the sialyl Le(x) derivative with 2-(tetradecyl)hexadecyl residue.

Original languageEnglish
Pages (from-to)131-133
Number of pages3
JournalCarbohydrate Research
Volume303
Issue number2
DOIs
Publication statusPublished - Sep 5 1997
Externally publishedYes

Fingerprint

Selectins
Galactose
Derivatives
Oxidation
5-acetylneuraminyl-(2-3)-galactosyl-(1-4)-(fucopyranosyl-(1-3))-N-acetylglucosamine

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Synthesis of the 3'-C-carboxymethyl Lewis X derivative : A novel selectin blocker. / Ishida, Hideharu; Hosokawa, Hiroyuki; Kondo, Hirosato; Kiso, Makoto; Hasegawa, Akira.

In: Carbohydrate Research, Vol. 303, No. 2, 05.09.1997, p. 131-133.

Research output: Contribution to journalArticle

Ishida, Hideharu ; Hosokawa, Hiroyuki ; Kondo, Hirosato ; Kiso, Makoto ; Hasegawa, Akira. / Synthesis of the 3'-C-carboxymethyl Lewis X derivative : A novel selectin blocker. In: Carbohydrate Research. 1997 ; Vol. 303, No. 2. pp. 131-133.
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