Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Cyclic peptides
Reexamination Certificate
2008-03-20
2011-10-25
Ha, Julie (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Cyclic peptides
C530S333000, C530S338000
Reexamination Certificate
active
08044173
ABSTRACT:
A process comprising substitution of an acceptor molecule comprising a group —XC(O)— wherein X is O, S, or NR8, where R8is C1-6alkyl, C6-12aryl or hydrogen, with a nucleophile, wherein the acceptor molecule is cyclised such that said nucleophilic substitution at —XC(O)— occurs without racemisation, is provided. This process has particular application for the production of a peptide by extension from the activated carboxy-terminus of an acyl amino acid residue without epimerisation.
REFERENCES:
patent: 4251438 (1981-02-01), Moon
patent: 6294539 (2001-09-01), Lou et al.
patent: 9517418 (1995-06-01), None
Dellaria, et al., “Enantioselective Synthesis of α-Amino Acid Derivatives via the Stereoselective Alkylation of a Homochiral Glycine Enolate Synthon”, J. Org. Chem., 1989, 54, 3916-3926.
Kashima, et al., “Nucleophilic Ring-Opening Reactions of Morpholin-2-ones. A Resolution ofd1-(Secondary-alkyl)amines” J. Org. Chem., 1989, 54, 789-792.
Lee, et al., “Asymmetric Synthesis and Epimerization of Aryloxazinones”, Bull. Korean Chem. Soc., 1999, 20:3, 264-266.
Dorow, R.L., et al., “A Novel, One-Pot Preparation of N-Methyl-α-Amino Acid Dipeptides from Oxazolidinones and Amino Acids,” Tetrahedron Letters, 40: 467-470 (1999).
Shrader, W.D., et al., “A Short Asymmetric Synthesis of N-α-FMOC-N-ō-BOC-α-Methyl-D-Ornithine,” Bioorganic & Medicinal Chemistry Letters, 5(19): 2207-2210 (1995).
Zhang, Y., et al., “A Facile Synthesis of L-analyl-peptides from 5-Oxazolidinone,” Hecheng Huaxue, pp. 125-127 (1999).
Pyne, Stephen G., et al., “Diastereoselective Addition of α-Hydroxyalkyl and α-Alkoxyalkyl Radicals to Chiral 4-Methyleneoxazolidin-5-ones,” Tetrahedron, 54: 5709-5720 (1998).
Seebach, D., et al., “N,O-Acetals from Pivalaldehyde and Amino Acids for the α-Alkylation with Self-Reproduction of the Center of Chirality. Enolates of 3-Benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones,” Helvetica Chimica Acta, 68: 1243:1250 (1985).
Kogan, T., et al., “The Synthesis of Chiral 3-Oxo-6-[(phenylmethoxy)carbonyl]-2-piperazineacetic Acid Esters Designed for the Presentation of an Aspartic Acid Side Chain. A Subsequent Novel Friedel Crafts Reaction,” Tetrahedron Letters, 33(47): 7089-7092 (1992).
Chen, et al., “Bioactive Pseudopeptidic Analogues and Cyclostereoisomers of Osteogenic Growth Peptide C-Terminal Pentapeptide, OGP(10-14)”, Journal of Medicinal Chemistry, Apr. 11, 2002, vol. 45, No. 8, pp. 1624-1632 XP002599698 ISSN: 0022-2623.
Le, et al., “Bioactive Peptidic Analogues and Cyclostereoisomers of the Minimal Antinociceptive Histogranin Fragment-(7-10)”, Journal of Medicinal Chemistry, Jul. 3, 2003, vol. 46, No. 14, pp. 3094-3101 XP002599699 ISSN: 0022-2623.
Tchertchian, et al., “Synthesis of Na-(1-Phenyl-2-mercaptoethyl) Amino Acids, New Building Blocks for Ligation and Cyclization at Non-Cysteine Sites: Scope and Limitations in Peptide Synthesis”, Journal of Organic Chemistry, Dec. 24, 2004, vol. 69, No. 26, pp. 9208-9214 XP002599697 ISSN: 0022-3263.
Harwood Laurence M.
Yan Ran
Ha Julie
Stoel Rives LLP
University of Reading
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