Synthesis of anti-inflammatory compounds, and novel trisaccharid

Details Synthesis of anti-inflammatory compounds, and novel trisaccharid Synthesis of anti-inflammatory compounds, and novel trisaccharid

1993-03-31

1995-06-20

Robinson, Douglas W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

5361231, 435 97, 435101, C07H 306, C08B 3700, C12P 1900, C12P 1904

Patent

active

054261783

ABSTRACT:
Anti-inflammatory compounds are useful, for example, in treating arthritis and heart attack patients. Novel oligosaccharides useful in the rapid synthesis of certain anti-inflammatory compounds are disclosed, as is a rapid method of synthesizing the oligosaccharides. Low pH can loosen the acceptor specificity of galactosyltransferase (lactose synthase: EC 2.4.1.22 ), allowing the rapid synthesis of novel oligosaccharides. The disaccharides cellobiose (.beta.1.fwdarw.4) , laminaribiose (.beta.1.fwdarw.3) , gentiobiose (.beta.1.fwdarw.6) and maltose (.alpha.1.fwdarw.4) acted as acceptors for lactose synthase under low pH conditions. From these four acceptors, the following four novel trisaccharides were synthesized: Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.3)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.4)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.6)-Glc and Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.alpha.1.fwdarw.4)Glc. These trisaccharides, and other oligosaccharides, may be synthesized in a few days with the disclosed technique, as opposed to the several months which would likely have been required with more traditional organic synthetic methods. These trisaccharides may be used as intermediates in the rapid synthesis of anti-inflammatory compounds.

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