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Volumn 118, Issue 30, 1996, Pages 7083-7093

CLEAR: A novel family of highly cross-linked polymeric supports for solid-phase peptide synthesis

Author keywords

[No Author keywords available]

Indexed keywords

GASTRIN; LEUCINE ENKEPHALINAMIDE;

EID: 0029778868     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954196s     Document Type: Article
Times cited : (163)

References (56)
  • 1
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    • Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd.: Kingswinford, England
    • For preliminary accounts of portions of this work, see: (a) Kempe, M.; Barany, G. In Peptides: Chemistry, Structure & Biology, Proceedings of the Fourteenth American Peptide Symposium; Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd.: Kingswinford, England, 1996; pp 865-866. (b) Kempe, M.; Barany, G. In Innovations and Perspectives in Solid Phase Synthesis and Combinatorial Chemical Libraries, 1995; Epton. R., Ed.; Mayflower Worldwide Ltd.: Kingswinford, England, 1996; in press.
    • (1996) Peptides: Chemistry, Structure & Biology, Proceedings of the Fourteenth American Peptide Symposium , pp. 865-866
    • Kempe, M.1    Barany, G.2
  • 2
    • 9344239454 scopus 로고    scopus 로고
    • Epton. R., Ed.; Mayflower Worldwide Ltd.: Kingswinford, England, in press
    • For preliminary accounts of portions of this work, see: (a) Kempe, M.; Barany, G. In Peptides: Chemistry, Structure & Biology, Proceedings of the Fourteenth American Peptide Symposium; Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd.: Kingswinford, England, 1996; pp 865-866. (b) Kempe, M.; Barany, G. In Innovations and Perspectives in Solid Phase Synthesis and Combinatorial Chemical Libraries, 1995; Epton. R., Ed.; Mayflower Worldwide Ltd.: Kingswinford, England, 1996; in press.
    • (1996) Innovations and Perspectives in Solid Phase Synthesis and Combinatorial Chemical Libraries, 1995
    • Kempe, M.1    Barany, G.2
  • 3
    • 0015522445 scopus 로고
    • Abbreviations used for amino acids and the designation of peptides follow the rules of the IUPAC-IUB Commission of Biochemical Nomenclature in J. Biol. Chem. 1972, 247, 977-983. The following additional abbreviations are used: AAA, amino acid analysis, AIBN, 2,2′-azobisisobutyronitrile; BOP, benzotriazolyl N-oxytris(dirnethylamino)phosphonium hexafluorophosphate; CLEAR, title supports of this paper, DIPCDI, N.N′-diisopropylcarbodiimide; DMF, N.N-dimethylformamide; EDT, 1,2-ethanedithiol, Fmoc, 9-fluorenylmethyloxycarbonyl; HPLC, high-performance liquid chromatography; HOAt, 1-hydroxy-7-azabenzotriazole; HOBt, 1-hydroxybenzotriazole; IRAA, internal reference amino acid; NMM, N-methyl morpholine; PAL, 5-(4-aminomethyl-3,5-dimethoxyphenoxy)-valeric acid; PEG, polyethylene glycol; PS, polystyrene; SEM, scanning electron microscopy; SPPS, solid-phase peptide synthesis; TFA. trifluoroacetic acid. All solvent ratios are volume/volume. All amino acids used were of the L-configuration.
    • (1972) J. Biol. Chem. , vol.247 , pp. 977-983
  • 5
    • 0001926444 scopus 로고
    • Gross. E., Meienhofer, J., Eds.; Academic Press: New York
    • (a) Barany, G.; Merrifield, R. B. In The Peptides; Gross. E., Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 2, pp 1-284.
    • (1979) The Peptides , vol.2 , pp. 1-284
    • Barany, G.1    Merrifield, R.B.2
  • 7
  • 16
    • 0005702862 scopus 로고
    • Meienhofer, J., Ed.; Ann Arbor Sci. Publ.: Ann Arbor. MI
    • (a) Tregear, W. In Chemistry and Biology of Peptides; Meienhofer, J., Ed.; Ann Arbor Sci. Publ.: Ann Arbor. MI, 1972; pp 175-178.
    • (1972) Chemistry and Biology of Peptides , pp. 175-178
    • Tregear, W.1
  • 45
    • 0030153492 scopus 로고    scopus 로고
    • (d) Kempe, M. Anal. Chem. 1996, 68, 1948-1953.
    • (1996) Anal. Chem. , vol.68 , pp. 1948-1953
    • Kempe, M.1
  • 49
    • 9344246402 scopus 로고    scopus 로고
    • note
    • 4OH for 2 weeks shows such a pattern [for details, see Experimental section; mass spectra are in supporting information: Figures 17-19]. FT-MS ESI performed under the same conditions on crude ACP(65-74) amide did not show this pattern of signals separated by 44 amu but only the expected signals due to the peptides [for spectra see supporting information: Figure 20].
  • 55
    • 9344222313 scopus 로고    scopus 로고
    • note
    • Commercial Fmoc-PAL-Nle-PEG-PS has a Nle IRAA between the PS and bifunctional PEG, which latter sometimes acts as a spacer and other times cross-links two Nle sites. Hence, ratios of incorporated amino acids to Nle of 2-3 represent quantitative yields past the PAL handle.


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