Synthesis and Selectin‐Blocking Activity of a Novel Analog of Sulfatide: 3‐C‐Carboxymethylgalactosyl Lipid

Autor:	Makoto Kiso, Hiromune Ando, Hideharu Ishida, Takao Ikami, Ai Ishihara, Noboru Tomiya
Rok vydání:	2003
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Residue (chemistry) Double bond chemistry Stereochemistry Galactose Organic Chemistry Swern oxidation Stereoselectivity Biochemistry Selectin
Zdroj:	Journal of Carbohydrate Chemistry. 22:513-520
ISSN:	1532-2327 0732-8303
DOI:	10.1081/car-120026455
Popis:	The 3‐C‐carboxymethylgalactose derivative carrying the 2‐(tetradecyl)hexadecyl residue, which was designed as a novel analog of sulfatide, was synthesized. A key intermediate, 3‐C‐carboxymethylgalactose, 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 3‐O‐sulfogalactose derivative with 2‐(tetradecyl)hexadecyl residue. †This paper is dedicated to Professor Gerard Descotes on the occasion of his 70th birthday. #Synthetic studies on sialoglycoconjugates, Part 131. For Part 130, see Ref. [1].
Databáze:	OpenAIRE
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