Method for making amino acid glycosides and glycopeptides

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Peptides containing saccharide radicals – e.g. – bleomycins – etc.

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530327, 530328, 530329, 530330, 530331, 564197, 564165, 562575, A61K 3800, C07K 500, C07K 700, C07K 1700

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active

054709490

ABSTRACT:
A compound of the formula ##STR1## is disclosed. X is selected from the group consisting of aryl, alkyl, imidate ester, imino ester, amidine, azide, isocyanate, and dithiocarbonate. R' is a group selected from the group consisting of groups containing a hydroxyl moiety, groups containing a protected hydroxyl moiety, and groups containing an O-linked sugar. G is a carbon chain of 0-10 carbons and R is not a methyl group and is a group capable of removal under conditions compatible with glycopeptide synthesis. In a preferred form the compound, R is selected from the group consisting of benzylic or allyl groups and X is CPh.sub.2. A method of forming a glycocide from the compound is also disclosed.

REFERENCES:
patent: 4518711 (1985-05-01), Hruby et al.
Bodor, et al., "A Strategy for Delivering Peptides into the Central Nervous ystem by Sequential Metabolism," Science, vol. 257:1698-1700 (1992).
Borman, Stu, "Blood-Brain Barrier Bridged by Molecular Packaging Technique," C&EN, pp. 57-58 (Oct. 5, 1992).
Polt, Et Al., "General Methods for Alpha- or Beta-O-Ser/Thr Glycosides and Glycopeptides. Solid Phase Synthesis of O-Glycosyl Cyclic Enkephalin Analogs," ACS Journal published Dec. 16, 1992.
Szabo, et al., "O-Glycopeptides: A Simple beta-Stereoselective Glycosidation of Serine and Threonine Via A Favorable Hydrogen Bonding Pattern," Tetrahedron Letters, 32:58 (1991).
Polt, et al., "Alpha- and Beta-O-Glycosides via Nucleophilic Activation by Hydrogen Bond Acceptors. New Synthetic Methods for O-Linked Glycopeptides and Glycosphingolipids," American Chemical Society Abstract, published Mar. 2, 1992.

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