Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1997-07-10
1999-09-14
Davis, Zinna Northington
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
560 19, C07D25308, C07C22900
Patent
active
059524979
ABSTRACT:
This invention relates to N.sup..alpha. -Bpoc amino acid pentafluorophenyl (Pfp) esters and 3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl (ODhbt) esters and side-chain protected derivatives thereof which are useful in peptide, polypeptide, and protein synthesis. The invention relates to the esters, their preparation and their use in peptide synthesis.
REFERENCES:
patent: 4192798 (1980-03-01), Verlander et al.
patent: 4351762 (1982-09-01), Verlander et al.
patent: 5011940 (1991-04-01), Urbach et al.
patent: 5233044 (1993-08-01), Hudson
Tikhonov et al, Chemical Abstracts 93:239,904e, p. 905, Dec. 22, 1980.
Shvachkin et al, Chemical Abstracts 94:175,510j, p. 773, May 25, 1981.
Kisfaludy, L. et al. (1973), "Die Verwendung von Pentafluorphenylestern bei Peptid-synthesen," Ann. Chem. 9:1421-1429.
Albericio, F., and Barany, G. (1987) "An acid-labile anchoring linkage for solid-phase synthesis of C-terminal peptide amides under mild conditions" Int. J. Peptide Protein Res. 30:206-216.
Atherton, E., and Sheppard, R.C. (1985) "Solid phase peptide synthesis using N.sub..alpha. -Fluorenylmethyoxycarbonylamino acid pentafluorophenyl esters" J. Chem. Soc. Chem. Comm., pp. 165-166.
Atherton, E., et al. (1988) "Peptide Synthesis. Part 12. 3,4-Dihydro-4-oxo-1, 2, 3-benzotriazin-3-yl Esters of Fluorenylmethoxycarbonyl Amino Acids as Self-indicating Reagents for Solid Phase Peptide Synthesis" J. Chem. Soc. Perkin Trans. 1:2887-2894.
Atherton, E., et al. (1988) "Peptide Synthesis. Part 10. Use of pentafluorophenyl esters of fluroenylmethoxycarboxyl amino acids in solid phase peptide synthesis" Tetrahedron 44:843-857.
Barany, G., et al. (1987) "Solid-phase peptide synthesis: a silver anniversary report" Int. J. Peptide Protein Res. 30:705-739.
Carey, R.I., et al. (1996) "Protection of asparagine and glutamine during N-Bpoc-based solid-phase peptide synthesis" Int. J. Peptide Prot. Res. 47(3):209-213.
Colombo, R. (1981) "Synthesis by an improved solid-phase method of a highly acidic peptide from mucleolar nonhistone protein C23" Bioorg. Chem. 10:219-232.
Feinberg, R.S., and Merrifield, R.B. (1972) "The synthesis of biphenylisopropyloxycarbonyl-amino acids salts" Tetrahedron 28:5865-5871.
Fotouhi, N., et al. (1989) "Peptide synthesis by prior thiol capture." J. Org. Chem. 54:2803-2817.
Fotouhi, N., et al. (1992) "Resolution of proline acylation problem for thiol capture strategy by use of a chloro-dibenzofuran template" Int. J. Peptide, Protein Res. 40:141-147.
Fotouhi, N. and Kemp, D.S. (1993) "Novel class of silicon-based protective groups for the side chain of tyrosine" Int. Peptide Protein Res. 41(2):153-161.
Galpin, I., et al. (1981) "Peptides-XXXXV. Synthesis of the 118-129 fragment of a lysozyme analogue" Tetrahedron 37(17):3037-3041.
Galpin, I., et al. (1979) "Peptides-XXXVI. Synthesis of the 27-37 fragment of a lysozyme analogue" Tetrahedron 35:2785-2790.
Galpin, I., et al. (1981) "Peptides-XXXXVI. Studies in the synthesis of an analogue of hen egg white lysozyme." Tetrahedron 37(17):3043-3050.
Guibe, F., et al. (1989) "Use of an allylic anchor group and of its palladium catalyzed hydrostannolytic cleavage in the solid phase synthesis of protected peptide fragments" Tetrahedron Lett. 30:2641-2644.
Hammond, G.S. and Reeder, C.E. (1958) "Benzyl tosylates. VI. The effects of phenyl as a substituent" J. Am. Chem. Soc. 80:573-575.
Hiskey, R.G., et al. (1972) "Sulfur-containing polypeptides. XVI. Synthesis of the A.sup.14-21 Fragment of ovine insulin" J. Org. Chem. 37(15):2478-2483.
Hudson, D. (1990) "Methodological implications of simultaneous solid-phase peptide synthesis: a comparison of active esters" Peptide Res. 3(1):51-55.
Hudson, D. (1988) "Methodological implications of simultaneous solid-phase peptide synthesis: 1. Comparison of different coupling procedures" J. Org. Chem. 53:617-624.
Juhasz, A., and Bajusz, S. (1979) "A novel amide-protecting group" Acta Chim. Acad. Sci. Hung. 102(3):289-296.
Kamber, B.., et al. (1976) "Syntheses von humaninsulin. III. Aufbau des geschutzten zweikettigen fragments A(14-21)--B(17-30)" Helv. Chim. Acta 59(8):2830-2840.
Kemp, D.S. (1981) "The amine capture strategy for peptide bond formation-An outline of progress" Biopolymers 20:1793-1804.
Kemp, D.S., and Carey R.I. (1993) "Synthesis of a 39-peptide and a 25-peptide by thiol capture ligations: observation of a 40-fold rate acceleration of the intramolecular O, N-acyl-transfer reaction between peptide fragments bearing only cysteine protective groups" J. Org. Chem. 58:2216-2222.
Kemp, D.S., et al. (1991) "Resolution of the histidine problem for thiol capture--synthesis of a 39-peptide" Tetrahedron Let. 32(25):2845-2848.
Kemp, D.S., et al. (1989) "Rational design of templates for intramolecular O, N-acyl-transfer via medium-sized cyclic intermediates derived from L-cysteine. Definition of an experimental maximum in effective molarity through the study of tunable templates" J. Org. Chem. 54:1589-1603.
Kemp, D.S., et al. (1988) Practical preparation and deblocking condition for N-x-(2-(p-biphenylyl)-2-propyloxycarbonyl)-amino acid (N-.alpha.-Bpoc-Xxx-OH) derivatives. Int. J. Peptide Protein Res. 31:359-372.
Kisfaludy, L., and Schon, I. April, 1983 "Preparation and applications of pentafluorophenyl esters of 9-fluorenylmethyloxycarbonyl amino acids for peptide synthesis" Synthesis pp. 325-327.
Koenig, W. and Geiger, R. (1970) "Eine neue Amid-Schutzgruppe" Chem. Ber. 103:2041.
Kovacs, J., et al. (1970) "Rates of racemization and coupling of cysteine active ester derivatives" J. Chem. Soc. Chem. Comm. 53-54.
Kovacs, J., et al. (1970) "Racemization of amino acids derivatives. Rate of racemization and peptide formation of cysteine active esters" J. Org. Chem. 35:1810-1815.
Kunz, H., and Dombo, B. (1988) "Solid phase synthesis of peptides and glycopeptides on polymeric supports with allylic anchor groups" Angew. Chem. Int. Ed. Engl. 27(5):711-713.
Mojsov, S., and Merrifield, R.B. "Solid phase synthesis of crystalline glucagon" (1981) Biochemistry 20:2950-2956.
Rosowsky, A., and Wright, J.E. (1989) "N.sup.e Tetra-L-lysine as potential intermediates in the block poLymer synthesis of macromolecular drug conjugates" J. Org. Chem. 54:5551-5558.
Rosowsky, A., and Wright, J.E. (1983) "N.sup.w -Alkoxycarbonylation of .sub..alpha.,w- Diamino Acids with 2-(Trimethylsily)ethyl 4-Nitrophenyl Carbonate" J. Org. Chem. 48:1539-1541.
Schon, I., and Kisfaludy, L. Apr., 1986 "9-Fluorenylmethyl pentafluorophenyl carbonate as a useful reagent for the preparation of N-9-Fluorenylmethyloxycarbonylamino acids and their pentafluorophenyl esters" Synthesis pp. 303-305.
Shimonishi, Y., et al. (1962) "Studies on the synthesis of peptides containing glutamine as the c-terminal. I. Protection of amide-nitrogen with xanthyl group during peptide syntehsis" Bull. Chem. Soc. Japan 35:1966-1970.
Schwertner, E., et al. (1975) "Synthese einiger Chem. pp.581-585.
Seitz, O., and Kuna, H. (1995) "A novel allylic anchor for solid-phase synthesis-synthesis of protected and unprotected O-glycosylated Mucin-type glycopeptides" Angew. Chem. Int. Ed. Engl. 34(7): 803-805.
Sieber, P. and Iselin, B. (1968) "Selektive acidolytsche Spaltung von Aralkyloxycarbonyl-Aminoschutzgruppen" Helv. Chim. Acta 51(4):614-622.
Sieber, P., and Iselin, B. (1968) "Peptidsynthesen unter verwendung der 2-(p-Diphenyl)-isopropyloxycarbonyl (Bpoc)-Aminoschutzgruppe" Helv. Chim. Acta 51(4):622-632.
Sieber, P., et al. (1977) "Totalsynthese von Humaninsulin. IV. Beschreibung der Endstufen" Helv. Chim. Acta 60:27-37.
Sieber, P. and Riniker, B. (1991) "Protection of carboxamide functions by the trityl residue application to peptide synthesis" Tetrahedron Lett. 32(6):739-742.
Trudelle, Y., and Heitz, F. (1987) "Synthesis and characterization of Tyr(Bzl) .sup.9,11,13,15 and Tyr.sup.9,11,13,15 gramicidin A" Int. J. Peptide Protein Res. 30:163-169.
Wang, S.S., and Kulesha, I.D. (1975) "Preparation of protected peptide intermediates for a synthesis of the ovine pituitary growth hormone sequence 96-135" J. Org. Chem 40(9):1227-1234.
Wang, S.S., and Merrifield, R.B. (1969) "Preparation of some new
Davis Zinna Northington
University of Georgia Research Foundation
LandOfFree
N.sup..alpha. -Bpoc amino acid pentafluorophenyl (Pfp) esters an does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with N.sup..alpha. -Bpoc amino acid pentafluorophenyl (Pfp) esters an, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N.sup..alpha. -Bpoc amino acid pentafluorophenyl (Pfp) esters an will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1511054