Chemical synthesis of reagents for peptide coupling

Details Chemical synthesis of reagents for peptide coupling Chemical synthesis of reagents for peptide coupling

2008-01-08

2008-01-08

Barts, Samuel A (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Boron containing

C564S123000, C530S402000

Reexamination Certificate

active

07317129

ABSTRACT:
The present invention provides improved methods for synthesis of phosphinothiol reagents, as well as novel protected reagents, for use in formation of amide bonds, and particularly, for peptide ligation. The invention provides phosphine-borane complexes useful as reagents in the formation of amide bonds, particularly for the formation of an amide bond between any two of an amino acid, a peptide, or a protein.

REFERENCES:
patent: 5300278 (1994-04-01), Pasqualini et al.
patent: 5541289 (1996-07-01), Gilbertson
patent: 5543389 (1996-08-01), Yatvin et al.
patent: 6974884 (2005-12-01), Raines et al.
patent: 2002/0016003 (2002-02-01), Saxon et al.
patent: 2003/0199084 (2003-10-01), Saxon et al.
patent: 0168565 (2001-09-01), None
patent: 0187920 (2001-11-01), None
patent: 0218417 (2002-03-01), None
patent: 03104243 (2003-12-01), None
Alfonso, C.A. (1998), “Studies on the Transformation of Azido-Group to N-(t-Butoxycarbonyl)amino Group via Staudinger Reaction,” Synthetic Commun. 28:261-276.
Ariza et al. (1998), “One-Pot Conversion of Azides to Boc-Protected Amines with Trimethylphosphine and Boc-ON,” Tetrahedron Lett. 39:9101-9102.
Ariza et al. (Jul. 2001), “From Vacinal Azido Alcohols to Boc-Amino Alcohols or Oxazolidinones, with Trimethylphosphine and Boc2O or CO2,” Tetrahedron Lett. 42:4995-4999.
Ayers et al. (Feb. 1999), “Introduction of Unnatural Amino Acids into Proteins Using Expressed Protein Ligation,” Biopolymers, 51:343-354.
Backes et al. (Mar. 1999), “An Alkanesulfonamide ‘Safety-Catch’ Linker for Solid-Phase Synthesis,” J. Org. Chem. 64:2322-2330.
Block et al. (1989), “2-Phosphino- and 2-Phosphinylbenzenethiols: New Ligand Types,” J. Am. Chem. Soc. 111: 2327-2329.
Borgia et al. (Jun. 2000), “Chemical Synthesis of Proteins,” Trends Biotechnol. 18:243-251.
Bosch et al. (1993) “Alternative Procedures for Macrolactamisation of Omega-Azido Acids,” Tetrahedron Lett. 34:4671-4674.
Bosch et al. (1995), “Epimerisation-free Peptide Formation from Carboxylic Acid Anhydrides and Azido Derivatives,” J. Chem. Soc., Chem. Commun., pp. 91-92.
Bosch et al. (1996), “On the Reaction of Acyl Chlorides and Carboxylic Anhydrides with Phosphazene,” J. Org. Chem. 61:5638-5643.
Boullanger et al. (Feb. 2000), “Syntheses of Amphiphilic Glycosylamides from Glycosyl Azides Without Transient Reduction to Glycosylamines,” Carbohydr. Res. 324:97-106.
Brik et al. (Jun. 2000), “Protein Synthesis by Solid-Phase Chemical Ligation Using a Safety Catch Linker,” J. Org. Chem. 65(12):3829-3835.
Brisset et al. (1993), “Phosphine-Borane Complexes; Direct Use in Asymmetric Catalysis,” Tetrahedron Lett. 34:4523-4526.
Bruice et al. (1960), “The Effect of Geminal Substitution Ring Size and Rotamer Distribution on the Intramolecular Nucleophilic Catalysis of the Hydrolysis of Monophenyl Esters of Dibasic Acids and the Solvolysis of the Intermediate Anhydrides,” J. Am. Chem. Soc. 82:5858-5865.
Brunel et al. (1998), “Phosphane-Boranes: Synthesis, Characterization and Synthetic Applications,” Coord. Chem. Rev. 180:665-698.
Cane et al. (1998), “Harnessing the Biosynthetic Code: Combinations, Permutations, and Mutations,” Science 282:63-68.
Carboni et al. (Jan. 1999), “Recent Developments in the Chemistry of Amine- and Phosphine-Boranes,” Tetrahedron 55:1197-1248.
Charrier et al. (1978), “La Diphenyl-Cyclopentadienylmethyl-Phosphine FT SFS Complexes,” (in French) Tetrahedron Lett. 27:2407-2410.
Cotton et al. (Sep. 1999), “Peptide Ligation and its Application to Protein Engineering,” Chem. Biol. 6: R247-R256.
Dawson et al. (Jul. 2000), “Synthesis of Native Proteins by Chemical Ligation,” Annu. Rev. Biochem. 69:923-960.
Dawson et al. (1994), “Synthesis of Proteins by Native Chemical Ligation,” Science 266:776-779.
Dawson et al. (1997), “Modulation of Reactivity in Native Chemical Ligation through the Use of Thiol Additives,” J. Am. Chem. Soc. 119:4325-4329.
Drijfhout et al. (Dec. 2000), Chemical Abstracts (Columbus, Ohio, USA) No. 133:135556. Abstract of “Methods of Preparing Peptide-Carrier Conjugates,” in Fmoc Solid Phase Peptide Synthesis), pp. 229-241.
Evans et al. (1998), “Semisynthesis of Cytotoxic Proteins Using a Modified Protein Splicing Element,” Protein Sci. 7:2256-2264.
Evans et al. (pub. on-line Feb. 2000), “Intein-Mediated Protein Ligation: Harnessing Nature's Escape Artists,” Biopolymers 51:333-342.
Farrington et al. (1989), “A Convenient Synthesis of Diethyl (Mercaptomethyl)Phosphonate,” Org. Prep. Proced. Int. 21:390-392.
Friedman, M. (Apr. 1999), “Lysinoalanine in Food and in Antimicrobial Proteins,” Adv. Exp. Med. Biol. 459:145-159.
Garcia et al. (1984), “New Synthetic “Tricks”. Triphenylphosphine-Mediated Amide Formation from Carboxylic Acids and Azides,” Tetrahedron Lett. 25:4841-4844.
Garcia et al.(1986), “New Synthetic “Tricks”. One-Pot Preparation of N-substituted Phthalimides from Azides and Phthalic Anhydride,” Tetrahedron Lett. 27:639-640.
Gilbertson, S. (Aug. 2001), “High-Yielding Staudinger Ligation of Phosphinoesters and Azides to Form Amides,” Chemtracts-Org. Chem. 14:524-528.
Gololobov et al. (1992), “Recent Advances in the Staudinger Reaction,” Tetrahedron 48:1353-1406.
Gololobov et al. (1981), “Sixty Years of Staudinger Reaction,” Tetrahedron 37: 437-472.
Holford et al. (1998), “Adding ‘Splice’ to Protein Engineering,” Structure 15: 951-956.
Imamoto et al. (1990), “Synthesis and Reactions of Phosphine-Boranes. Synthesis of New Bidentate Ligands with Homochiral Phosphine Centers via Optically Pure Phosphine-Boranes,” J. Am. Chem. Soc. 112:5244-5252.
Inazu et al. (1993), “A New Simple Method for the Synthesis of Nα-Fmoc-Nβ-Glycosylated-L-Asparagine Derivatives,” Synlett., pp. 869-870.
Ingenito et al. ( Nov. 1999), “Solid Phase Synthesis of Peptide C-Terminal Thioesters by Fmoc/t-Bu Chemistry,” J. Am. Chem. Soc. 121:11369-11374.
Janssen, M. J. The Chemistry of Carboxylic Acids and Esters: Patai, S., Ed.; Interscience Publishers: New York, 1969; pp. 730-736.
Jung et al. (1991), “Gem-Dialkyl Effect in the Intramolecular Diels-Alder Reaction of 2-Furfuryl Methyl Fumarates: The Reactive Rotamer Effect, Enthalpic Basis for Acceleration, and Evidence for a Polar Transition State,” J. Am. Chem. Soc. 113: 224-232.
Kaiser, E. T. (1989), “Synthetic Approaches to Biologically Active Peptides and Proteins Including Enzymes,” Acc. Chem. Res. 22:47-54.
Katz, L. (1997), “Manipulation of Modular Polyketide Syntheses,” Chem. Rev. 97:2557-2575.
Keating et al. (Oct. 1999), “Initiation, Elongation, and Termination Strategies in Polyketide and Polypeptide Antibiotic Biosynthesis,” Curr. Opin.Chem. Biol. 3:598-606.
Kemp et al. (1986), “Peptide Synthesis by Prior Thiol Capture. 1. A Convenient Synthesis of 4-Hydroxy-6-mercaptodibenzofuran and Novel Solid-Phase Synthesis of Peptide-Derived 4-(Acyloxy)-6-mercaptodibenzofurans,” J. Org. Chem. 51:1821-1829.
Kent, S. B. (1988), “Chemical Synthesis of Peptides and Proteins,” Annu. Rev. Biochem. 57: 957-989.
Khosla, C. (1997), “Harnessing the Biosynthetic Potential of Modular Polyketide Synthases,” Chem. Rev. 97:2577-2590.
Kiick et al. (Jan. 2002), “Incorporation of Azides into Recombinant Proteins for Chemoselective Modification by the Slaudinger Ligation,” Proc. Natl. Acad. Sci. USA 99:19-24.
Kochendoerfer et al. (Dec. 1999), “Chemical Protein Synthesis,” Curr. Opin. Chem. Biol. 3:665-671.
Konz et al. (Feb. 1999), “How do Peptide Synthetases Generate Structural Diversity?”

Affiliated with

Also associated with

Rating

Chemical synthesis of reagents for peptide coupling does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Chemical synthesis of reagents for peptide coupling, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chemical synthesis of reagents for peptide coupling will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2800320