Synthesis of Le.sup.x ; dimeric Le.sup.x (difucosyl Y.sub.2 ; III.sup.3 FucV.sup.3 FucnLc.sub.6 Cer); sialylated forms thereof; and analogues thereof

US5421733A · kind A · utility

Assignee

• The Biomembrane Institute · US

Inventors

• Edward Nudelman · Seattle, US
• Khalid Sadozai · Hofheim, DE
• Henrik Clausen · Seattle, US
• Sen-itiroh Hakomori · Seattle, US
• Mark Stroud · Seattle, US

Key dates

• Filing date: May 24, 1991
• Grant date: Jun 6, 1995
• Expiry date: May 24, 2011

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C12P19/04
• WIPO field: Biotechnology
• WIPO sector: Chemistry

Abstract

A process for preparing difucosyl Y.sub.2 antigen (dimeric Le.sup.x) , said process comprising: (1) preparing a lactonorhexaosylceramide backbone or a lactonorhexaosylsaccharide backbone linked to a carrier molecule; and (2) enzymatically fucosylating said backbone at the III.sup.3 and V.sup.3 positions through an .alpha.1.fwdarw.3 linkage. A process for preparing Le.sup.y antigen analogues, said process comprising: (1) preparing a lactonorhexaosyl-ceramide backbone or a lactonorhexaosylsaccharide backbone linked to a carrier molecule; and (2) enzymatically fucosylating said backbone at the terminal .beta.-Gal through an .alpha.1.fwdarw.2 linkage; and (3) enzymatically fucosylating said backbone at one or more positions through an .alpha.1.fwdarw.3 linkage, provided that steps (2) and (3) can be conducted simultaneously or in any order. A process for preparing a fucosylated lactonorhexaosylceramide, lactonorhexaosylsaccharide linked to a carrier molecule or higher analogues thereof, said process comprising: (1) preparing a lactonorhexaosylceramide backbone, a lactonorhexaosylsaccharide backbone linked to a carrier molecule or backbones of higher analogues thereof; and (2) enzymatic…