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Volumn 10, Issue 21, 2008, Pages 4847-4850

Versatile synthesis of head group functionalized phospholipids via oxime bond formation

Author keywords

[No Author keywords available]

Indexed keywords

CHELATING AGENT; COPPER; OXIME; PHOSPHOLIPID;

EID: 58149156304     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8019346     Document Type: Article
Times cited : (6)

References (39)
  • 1
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    • For examples, see: a
    • For examples, see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503.
    • (1996) Acc. Chem. Res , vol.29 , pp. 503
    • Prestwich, G.D.1
  • 12
    • 1842739440 scopus 로고    scopus 로고
    • Wang, P.; Blank, D. H.; Spencer, T. A. J. Org. Chem. 2004, 69, 2693. See also, ref 1a.
    • Wang, P.; Blank, D. H.; Spencer, T. A. J. Org. Chem. 2004, 69, 2693. See also, ref 1a.
  • 20
    • 33845191735 scopus 로고    scopus 로고
    • The oxime bond formation (oxime ligation) has been used to conjugate functional groups, such as fluorescent label, to biomolecules. See the following reference and references cited therein: Dirksen, A.; Hackeng, T. M.; Dawson, P. E. Angew. Chem., Int. Ed. 2006, 45, 7581.
    • The oxime bond formation (oxime ligation) has been used to conjugate functional groups, such as fluorescent label, to biomolecules. See the following reference and references cited therein: Dirksen, A.; Hackeng, T. M.; Dawson, P. E. Angew. Chem., Int. Ed. 2006, 45, 7581.
  • 30
    • 60949090547 scopus 로고    scopus 로고
    • For details of how the cyclen 6f was prepared, see the Supporting Information.
    • For details of how the cyclen 6f was prepared, see the Supporting Information.
  • 31
    • 0029074762 scopus 로고    scopus 로고
    • For protein cleavage by the 1,10-phenanthroline-Cu(II) complex, see: (a) Wu, J.; Perrin, D. M.; Sigman, D. S.; Kaback, H. R. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9186.
    • For protein cleavage by the 1,10-phenanthroline-Cu(II) complex, see: (a) Wu, J.; Perrin, D. M.; Sigman, D. S.; Kaback, H. R. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9186.
  • 32
    • 60949085834 scopus 로고    scopus 로고
    • Galasco, A.; Crouch, R. K.; Knapp, D. R. Biochemistry 2000, 39, 4907. For protein cleavage by the cyclen-Cu(II) complex, see the following references and references cited therein: Jang, S. W.; Suh, J. Org. Lett. 2008, 10, 481.
    • (b) Galasco, A.; Crouch, R. K.; Knapp, D. R. Biochemistry 2000, 39, 4907. For protein cleavage by the cyclen-Cu(II) complex, see the following references and references cited therein: Jang, S. W.; Suh, J. Org. Lett. 2008, 10, 481.
  • 34
    • 60949100468 scopus 로고    scopus 로고
    • 2c, 2d, and 8f and visualizing bands for HA1 and HA2, both of which correspond to HA. We had difficulty applying the phenantriroline phospholipids 8e to membrane reconstitution due to its insolubility in the 5% octylglucoside solution
    • Determined by running SDS-PAGE on the precipitates from 2a
    • Determined by running SDS-PAGE on the precipitates from 2a, 2c, 2d, and 8f and visualizing bands for HA1 and HA2, both of which correspond to HA. We had difficulty applying the phenantriroline phospholipids 8e to membrane reconstitution due to its insolubility in the 5% octylglucoside solution. See the Supporting Information.
    • See the Supporting Information
  • 36
    • 24644489051 scopus 로고    scopus 로고
    • Staining with biotin-ConA also decreased the HA1 band. Cleaved HA fragments were visualized as smears by immunostaining with anti-P50 (H1N2) rabbit polyclonal antibody. See Supporting Information. For anti-P50, see: Suzuki, T.; Takahashi, T.; Guo, C.-T.; Hidari, K. I.-P. J.; Miyamoto, D.; Goto, H.; Kawaoka, Y.; Suzuki, Y. J. Virol. 2005, 79, 11705.
    • Staining with biotin-ConA also decreased the HA1 band. Cleaved HA fragments were visualized as smears by immunostaining with anti-P50 (H1N2) rabbit polyclonal antibody. See Supporting Information. For anti-P50, see: Suzuki, T.; Takahashi, T.; Guo, C.-T.; Hidari, K. I.-P. J.; Miyamoto, D.; Goto, H.; Kawaoka, Y.; Suzuki, Y. J. Virol. 2005, 79, 11705.
  • 37
    • 60949107244 scopus 로고    scopus 로고
    • 2 and sodium ascorbate. See Supporting Information.
    • 2 and sodium ascorbate. See Supporting Information.
  • 38
    • 60949091551 scopus 로고    scopus 로고
    • For the cleavage of HA with 2c and 2d, see Supporting Information.
    • For the cleavage of HA with 2c and 2d, see Supporting Information.
  • 39
    • 60949092470 scopus 로고    scopus 로고
    • Pyrene and 2-hydroxynaphthalene themselves did not show cleavage activity. See Supporting Information.
    • Pyrene and 2-hydroxynaphthalene themselves did not show cleavage activity. See Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.