메뉴 건너뛰기




Volumn 56, Issue 2, 2000, Pages 80-87

A solid-phase synthetic strategy for the preparation of peptide-based affinity labels: Synthesis of dynorphin A analogs

Author keywords

Allyloxycarbonyl (Alloc); Dynorphin analogs; Opioid peptide analogs; Orthogonal protection strategy

Indexed keywords

ACETAMIDE DERIVATIVE; AMINO ACID DERIVATIVE; CARBONYL DERIVATIVE; DYNORPHIN DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; MACROGOL; OPIATE PEPTIDE; PALLADIUM; POLYSTYRENE;

EID: 0033856249     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00736.x     Document Type: Article
Times cited : (17)

References (20)
  • 2
    • 0000092188 scopus 로고    scopus 로고
    • Analgesics
    • Therapeutic Agents (M.E. Wolff, ed.). John Wiley, New York
    • 2. Aldrich, J.V. (1996) Analgesics. In Burger's Medicinal Chemistry and Drug Discovery, Vol. 3: Therapeutic Agents (M.E. Wolff, ed.). John Wiley, New York, pp. 321-441.
    • (1996) Burger's Medicinal Chemistry and Drug Discovery , vol.3 , pp. 321-441
    • Aldrich, J.V.1
  • 4
    • 0031058301 scopus 로고    scopus 로고
    • Affinity labelling of frog brain opioid receptors by dynorphin(1-10) chloromethyl ketone
    • 4. Benyhe, S., Ketevan, A., Simon, J., Hepp, J., Medzihradszky, K. & Borsodi, A. (1997) Affinity labelling of frog brain opioid receptors by dynorphin(1-10) chloromethyl ketone. Neuropeptides 31, 52-59.
    • (1997) Neuropeptides , vol.31 , pp. 52-59
    • Benyhe, S.1    Ketevan, A.2    Simon, J.3    Hepp, J.4    Medzihradszky, K.5    Borsodi, A.6
  • 5
    • 0028099973 scopus 로고
    • Synthesis of enkephalin-based affinity labels for delta opioid receptors
    • 5. Maeda, D.Y., Murray, T.F., Roth, J.E. & Aldrich, J.V. (1994) Synthesis of enkephalin-based affinity labels for delta opioid receptors. Regul. Peptides 54, 171-172.
    • (1994) Regul. Peptides , vol.54 , pp. 171-172
    • Maeda, D.Y.1    Murray, T.F.2    Roth, J.E.3    Aldrich, J.V.4
  • 6
    • 0027279553 scopus 로고
    • Automated allyl deprotection for continuous-flow synthesis of cyclic and branched-peptides
    • 6. Kates, S.A., Daniels, S.B. & Albericio, F. (1993) Automated allyl deprotection for continuous-flow synthesis of cyclic and branched-peptides. Anal. Biochem. 212, 303-310.
    • (1993) Anal. Biochem. , vol.212 , pp. 303-310
    • Kates, S.A.1    Daniels, S.B.2    Albericio, F.3
  • 7
    • 0019161433 scopus 로고
    • Synthesis of p-amino-L-phenylalanine derivatives with protected p-amino group for preparation of p-azido-l-phenylalanine peptides
    • 7. Fahrenholz, F. & Thierauch, K.-H. (1980) Synthesis of p-amino-L-phenylalanine derivatives with protected p-amino group for preparation of p-azido-L-phenylalanine peptides. Int. J. Peptide Protein Res. 15, 323-330.
    • (1980) Int. J. Peptide Protein Res. , vol.15 , pp. 323-330
    • Fahrenholz, F.1    Thierauch, K.-H.2
  • 8
    • 0026494942 scopus 로고
    • Effect of modification of the basic residues of dynorphin A-(1-13) amide on κ opioid receptor selectivity and opioid activity
    • 8. Snyder, K.R., Story, S.C., Heidt, M.E., Murray, T.F., DeLander, G.E. & Aldrich, J.V. (1992) Effect of modification of the basic residues of dynorphin A-(1-13) amide on κ opioid receptor selectivity and opioid activity. J. Med. Chem. 35, 4330-4333.
    • (1992) J. Med. Chem. , vol.35 , pp. 4330-4333
    • Snyder, K.R.1    Story, S.C.2    Heidt, M.E.3    Murray, T.F.4    DeLander, G.E.5    Aldrich, J.V.6
  • 10
    • 0025103048 scopus 로고
    • A cleavage method which minimizes side reactions following fmoc solid phase peptide synthesis
    • 10. King, D.S., Fields, C.G. & Fields, G.B. (1990) A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis. Int. J. Peptide Protein Res. 36, 255-266.
    • (1990) Int. J. Peptide Protein Res. , vol.36 , pp. 255-266
    • King, D.S.1    Fields, C.G.2    Fields, G.B.3
  • 12
    • 33845282500 scopus 로고
    • Selective cleavage of the allyl and allyloxycarbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride: Application to the selective protection-deprotection of amino acid derivatives and in peptide synthesis
    • 12. Dangles, O., Guibe, F., Balavoine, G., Lavielle, S. & Marquet, A. (1987) Selective cleavage of the allyl and allyloxycarbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride: application to the selective protection-deprotection of amino acid derivatives and in peptide synthesis. J. Org. Chem. 52, 4984-4993.
    • (1987) J. Org. Chem. , vol.52 , pp. 4984-4993
    • Dangles, O.1    Guibe, F.2    Balavoine, G.3    Lavielle, S.4    Marquet, A.5
  • 13
    • 0011471348 scopus 로고
    • Allyl based side-chain protection for SPPS
    • (J.A. Smith & J. Rivier, eds). ESCOM, Leiden, The Netherlands
    • 13. Lyttle, M.H. & Hudson, D. (1992) Allyl based side-chain protection for SPPS. In Peptides: Chemistry and Biology (J.A. Smith & J. Rivier, eds). ESCOM, Leiden, The Netherlands, pp. 583-584.
    • (1992) Peptides: Chemistry and Biology , pp. 583-584
    • Lyttle, M.H.1    Hudson, D.2
  • 15
    • 0027527619 scopus 로고
    • Allyl-based groups for side-chain protection of amino-acids
    • 15. Loffet, A. & Zhang, H. (1993) Allyl-based groups for side-chain protection of amino-acids. Int. J. Peptide Protein Res. 42, 346-351.
    • (1993) Int. J. Peptide Protein Res. , vol.42 , pp. 346-351
    • Loffet, A.1    Zhang, H.2
  • 16
    • 0345663085 scopus 로고
    • Novel polyethyleneglycol polystryrene (PEG-PS) graft supports for solid-phase peptide synthesis
    • (C.H. Schneider & A.N. Eberle, eds). ESCOM, Leiden, The Netherlands
    • 16. Barany, G., Albericio, F., Solé, N.A., Griffin, G.W., Kates, S.A. & Hudson, D. (1993) Novel polyethyleneglycol polystryrene (PEG-PS) graft supports for solid-phase peptide synthesis. In Peptides 1992 (C.H. Schneider & A.N. Eberle, eds). ESCOM, Leiden, The Netherlands, pp. 267-268.
    • (1993) Peptides 1992 , pp. 267-268
    • Barany, G.1    Albericio, F.2    Solé, N.A.3    Griffin, G.W.4    Kates, S.A.5    Hudson, D.6
  • 17
    • 0029171257 scopus 로고
    • Synthesis, characterization and biocompatibility of PEG resins
    • 17. Auzanneau, F.-I., Meldal, M. & Bock, K. (1995) Synthesis, characterization and biocompatibility of PEG resins. J. Peptide Sci. 1, 31-44.
    • (1995) J. Peptide Sci. , vol.1 , pp. 31-44
    • Auzanneau, F.-I.1    Meldal, M.2    Bock, K.3
  • 18
    • 0001765482 scopus 로고
    • Properties of swollen polymer networks. Solvation and swelling of peptide-containing resin in solid phase peptide synthesis
    • 18. Sarin, V.K., Kent, S.B.H. & Merrifield, R.B. (1980) Properties of swollen polymer networks. Solvation and swelling of peptide-containing resin in solid phase peptide synthesis. J. Am. Chem. Soc. 102, 5463-5470.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5463-5470
    • Sarin, V.K.1    Kent, S.B.H.2    Merrifield, R.B.3
  • 19
    • 0001312564 scopus 로고
    • New rules of selectivity: Allylic alkylations catalyzed by palladium
    • 19. Trost, B.M. (1980) New rules of selectivity: allylic alkylations catalyzed by palladium. Acc. Chem. Res. 13, 385-393.
    • (1980) Acc. Chem. Res. , vol.13 , pp. 385-393
    • Trost, B.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.