US 5,795,958 AGranted

Library of glyco-peptides useful for identification of cell adhesion inhibitors

AssigneeGlycomed Incorporated

InventorsNarasinga Rao, Morten Meldal, Klaus Bock, Ole Hindsgaul

Life of this patent

Estimating the term…

Abstract

Glycopeptides having the following structure are described: ##STR1## wherein: X.sub.1 is hydrogen, an acetyl group, an acyl group or amino acid; R is .alpha.-L-fucose, .alpha.-D-fucose, .beta.-L-fucose or .beta.-D-fucose, wherein R is O-glucosidically linked to A.sub.1 ; A.sub.1 is serine, threonine, tyrosine, hydroxyproline, asparagine, glutamine, homeoserine and hydroxylysine; A.sub.2 is a glycine, an L-amino acid, a D-amino acid or a modified amino acid; A.sub.3 is L or D aspartic acid, glycine or glutamic acid; and X.sub.2 is a hydroxyl, an amine or an amino acid.

Claims7

Dependent claims

A glycopeptide selected from the group consisting of:

Ac-Ser(.alpha.-L-Fuc)-Asp-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Ser-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Phe-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Asn-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Leu-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Pro-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Gly-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asp-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Leu-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asn-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Ala-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Ala-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Ser-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Pro-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Arg-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-P he-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Ser-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Asn-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Asp-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Leu-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Gly-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Pro-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Arg-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-P he-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Ser-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Asn-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Asp-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Leu-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Gly-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Pro-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Arg-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Phe-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Ser-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Asn-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Asp-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Leu-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Gly-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Pro-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Arg-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Phe-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Ser-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Asn-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Asp-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Leu-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Gly-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Pro-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Arg-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Phe-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Ser-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Asn-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Asp-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Leu-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Gly-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Pro-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Arg-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Phe-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Ser-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asn-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asp-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Leu-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Gly-Glu-NH.sub.2, and
Ac-Ser(.beta.-L-Fuc)-Pro-Glu-NH.sub.2.

59 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/664,303Filed 10 Jun 1996 · continuation
Priority: 12 Oct 1993
Granted: 18 Aug 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07K 9/001
Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof: the peptide…
A61P 5/00
Drugs for disorders of the endocrine system
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
A61P 35/00
Antineoplastic agents

Family

Serial134,958Parent of this continuation · filed 12 Oct 1993
US 5,795,958 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Citations

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Abstract

A glycopeptide selected from the group consisting of:

Ac-Ser(.alpha.-L-Fuc)-Asp-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Ser-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Phe-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Asn-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Leu-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Pro-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Gly-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asp-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Leu-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asn-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Ala-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Ala-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Ser-Asp-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Pro-Asp-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Arg-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-P he-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Ser-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Asn-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Asp-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Leu-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Gly-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Pro-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Arg-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-P he-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Ser-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Asn-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Asp-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Leu-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Gly-Asp-OH,
Ac-Ser(.beta.-L-Fuc)-Pro-Asp-OH,
Ac-Ser(.alpha.-L-Fuc)-Arg-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Phe-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Ser-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Asn-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Asp-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Leu-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Gly-Gly-OH,
Ac-Ser(.alpha.-L-Fuc)-Pro-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Arg-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Phe-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Ser-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Asn-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Asp-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Leu-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Gly-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Pro-Gly-OH,
Ac-Ser(.beta.-L-Fuc)-Arg-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Phe-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Ser-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Asn-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Asp-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Leu-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Gly-Glu-NH.sub.2,
Ac-Ser(.alpha.-L-Fuc)-Pro-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Arg-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Phe-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Ser-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asn-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Asp-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Leu-Glu-NH.sub.2,
Ac-Ser(.beta.-L-Fuc)-Gly-Glu-NH.sub.2, and
Ac-Ser(.beta.-L-Fuc)-Pro-Glu-NH.sub.2.

59 more elements

Facts

Application

08/664,303Filed 10 Jun 1996 · continuation

Priority

12 Oct 1993

Granted

18 Aug 1998

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07K 9/001
Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof: the peptide…
A61P 5/00
Drugs for disorders of the endocrine system
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
A61P 35/00
Antineoplastic agents