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US 5,508,387 AGranted
Selectin binding glycopeptides
AssigneeGlycomed Incorporated
InventorsPeng C. Tang, Daniel E. Levy, Kevin R. Holme, Saeed A. Abbas
Life of this patent
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Abstract
Glyco-amino acids or glycopeptides that have three-dimensionally stable configuration for the presentation of functional groups, fucose, or an analogue or derivative thereof, covalently linked to an amino acid or peptide with a free carboxylic acid group, that facilitate binding between those groups and receptors on selectins, represented by the general structural formula I.
Claims8
A compound comprising the following structural Formula I:
- ##STR18## wherein m and u are integers of from 1 to 2;
- p, q and w are integers of from 1 to 6;
- r and s are integers of from 0 to 1;
- and t is an integer of from 0 to 3;
- and
- A is --COOH or --CH.sub.2 OSO.sub.3 H;
- B is --R.sup.1, --CH(R.sup.1).sub.2, --CH.sub.2 OCH.sub.2 R.sup.1 or --CH.sub.2 SCH.sub.2 R.sup.1 ;
- D is --L.sup.1 --(CH.sub.2).sub.w --CO--Q or --L.sup.2 --(CH.sub.2).sub.w --CO--Q;
- E is H or --(CH.sub.2).sub.w --{K--(CH.sub.2).sub.q }.sub.r --CO--Q with the proviso that when G is H, then E is --(CH.sub.2).sub.w --{K--(CH.sub.2).sub.q }.sub.r --CO--Q;
- G is H or --{K--(CH.sub.2).sub.q }.sub.r --CO--Q with the proviso that when E is H, then G is --{K--(CH.sub.2).sub.q }.sub.r --CO--Q;
- J is --SO.sub.2 -- when D is --L.sup.1 --(CH.sub.2).sub.w --CO--Q;
- or
- J is --CO-- or --CS-- when D is --L.sup.2 --(CH.sub.2).sub.w --CO--Q;
- K is --O--, --S--, --NH--, --S--S--, --CO-- or --CONH--;
- L.sup.1 is --NH--, --CH.sub.2 --, --NHR.sup.1 or --R.sup.4 ;
- L.sup.2 is --O--, --S--, --NH--, --CH.sub.2 --, --OR.sup.4, --SR.sup.4, --NHR.sup.1 or --R.sup.4 ;
- Q is selected from the group consisting of proteins and peptides;
- X is --R.sup.2, --OR.sup.2 or --CH.sub.2 OR.sup.2 ;
- Y is --(CHR.sup.3).sub.t -- with the proviso that there are no more than two OH groups;
- or --O--(CHR.sup.3).sub.u -- with the proviso that there is no more than one OH group;
- wherein
- R.sup.1 and R.sup.2 are independently H, an alkyl group containing 1 to 6 carbon atoms, aryl group or an arylalkyl group;
- R.sup.3 is H or OH;
- R.sup.4 is an alkyl group containing 1 to 6 carbon atoms, aryl group or an arylalkyl group;
- and
- Z is ##STR19##
23 more elements
Dependencies are inferred from the claim text.