Tumor-associated antigen synthesis synthesis of the gal-α-(1→3)-gal-β-(1→4)-GlcNAc epitope a specific determinant for metastatic progression?

✍ Scribed by Schaubach, Regine ;Hemberger, Jürgen ;Kinzy, Willy

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 925 KB
• Volume: 1991
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1991199101113

✦ Synopsis

Abstract

A versatile synthesis of the Gal‐α‐(1→3)‐Gal‐β‐(1→4)‐GlcNAc epitope coupled to an alkyl spacer molecule could be developed. The important building block 3′‐allyl‐D‐lactal 6 was prepared in high yield by the action of dibutyltin oxide and allyl bromide on D‐lactal and converted in several steps into the lactosamine derivative 13 with free 3′‐OH group. Stereoselective glycosidation with the β‐trichloroacetimidate of benzylated D‐galactose 18 led to the trisaccharide in high yield. Activation of the protected Gal‐α‐(1→3)‐Gal‐β‐(1→4)‐GlcNAc derivative 21 by desilylation and trichloroacetimidate formation followed by glycosidation with ethyl 9‐hydroxynonanoate furnished the spacer‐bound trisaccharide hapten 24 in excellent yield after simple two‐step deprotection. The trisaccharide hapten 24 can easily be used as immunogen after coupling to an immunogenic carrier.