Betides and methods for screening peptides using same

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

530326, 530327, 530328, 530329, 530330, C07K 100

Patent

active

056819285

ABSTRACT:
Compounds are provided termed "betides" which mimic peptides and which contain one or more residues of aminoglycine, C.sup..alpha. -aminoalanine, aminosarcosine or the like wherein the side chain amino group has been acylated and optionally also alkylated. Generally, betides have the formula:
X.sub.N --X.sub.1 --X.sub.2 --X.sub.3 --X.sub.m --X.sub.4 --X.sub.5 --X.sub.6 --X.sub.C, where X.sub.N is an acyl or other N-terminal group or a peptide up to about 50 amino acids in length having such a group; X.sub.C is OH, NH.sub.2 or other C-terminal group or a peptide up to about 50 amino acids in length having such a group; and X.sub.1 -X.sub.6 are each independently a betide amino acid or .alpha.-amino acid or des-X; and X.sub.m is a peptide up to about 50 amino acids or des-X; provided however that at least one of X.sub.1 -X.sub.6 is a betide amino acid residue having the formula: ##STR1## wherein R.sub.o is H or CH.sub.3, R and R.sub.2 are H or lower alkyl, and R.sub.3 is an acyl group, an isocyanate group, an isothiocyanate group or a sulfonyl group. In methods for making betides, an aminoglycine residue can be subjected to side chain acylation, and optionally also alkylation, after it has been incorporated into a peptide intermediate. This method can be used as a valuable tool to synthesize and screen multiple substituents at one or more positions in a peptide, permitting simultaneous screening of betides which mimic peptides having a large number of natural or unnatural amino acid substituents at a particular position, and optionally both D- and L-isomers of those substituents.

REFERENCES:
patent: 5110904 (1992-05-01), Haviv et al.
patent: 5169932 (1992-12-01), Hoeger et al.
patent: 5169935 (1992-12-01), Hoeger et al.
patent: 5296468 (1994-03-01), Hoeger et al.
Qasmi et al., "An -Aminoglycine Derivative Suitable for Soled Phase Peptide Synthesis Using Fmoc Strategy", Tetrahedron Letters, vol.34, No. 24, pp. 3861-3862, 1993.
Bock et al., "Differentially Protected -Aminoglycine", J. Org. Chem., vol. 51, No. 19, pp. 3718-3720, 1986.
Katrinzky et al., "Benzotriazole-assisted Synthesis of Monoacyl -Aminoglycines", J. Chem Soc. Chem. Commun., pp. 337-338, 1989.
Schmidt et al., "Synthesis of Differently Protected .alpha.-Aminoglycines and Their Peptide Derivatives", Short Papers, pp. 890-892, Sep. 1994.
Simon et al., "Peptoids: A modular approach to drug discovery", Proc. Natl. Acad. Sci.. USA, vol. 89, pp. 9367-9371, Oct. 1992.
Kawai et al., "Optical Resolution of N-Carbobenzoxy-.alpha.-methoxyglycine", Tetrahedron: Asymmetry, vol. 3, No. 8, pp. 1019-1020, Pergamon Press Ltd., Great Britain, 1992.
Schmidt et al., "The Total Synthesis of Lyciumins A and B.sup.1 ", J. Chem. Soc., Chem. Commun., pp. 1353-1354, 1992.
Rivier et al., "Gonadotropin-Releasing Hormone Antagonists with N.sup.107 -Triazolylornithine,-lysine, or -p-aminophenylalanine Residues at Positions 6 and 6", Journal of Med. Chem., vol. 35, No. 23, pp. 4270-4278, 1992.
Rivier et al., "Gonadotropin Releasing Hormone Antagonists: Novel Structures Incorporating N.sup..omega. -Cyano Modified Guanidine Moieties", Biochem. & Biophys. Research Communications, vol. 176, No. 1, pp. 406-412, Apr. 15, 1991.
Theobald et al., "General Method for Incorporation of Modified N.sup..omega. -Cyanoguanidino Moieties on Selected Amino Functions during Solid-Phase Peptide Synthesis", J. Am. Chem. Soc., vol. 112, No. 26, pp. 9624-9626, 1990.
Zoller et al., "Amidoalkylation of Mercaptans with Glyoxylic Acid Derivatives", Tetrahedron, vol. 31, pp. 863-866, Pergamon Press Ltd., Great Britain, 1975.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Betides and methods for screening peptides using same does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Betides and methods for screening peptides using same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Betides and methods for screening peptides using same will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1027092

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.