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Volumn 75, Issue 6, 2010, Pages 2069-2072

Double selective synthetic approach to the n-functionalized 1,4,7-triazacyclononane derivatives: chelating compounds for controllable protein orientation

Author keywords

[No Author keywords available]

Indexed keywords

CHELATING COMPOUND; CHEMICAL EQUATIONS; FUNCTIONALIZATIONS; FUNCTIONALIZED; HISTIDINE-TAGGED PROTEINS; NANO PATTERN; PENDANT ARMS; PROTEIN ORIENTATION; SYNTHETIC APPROACH; SYNTHETIC ROUTES; TRIAZACYCLONONANE;

EID: 77949808929     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902504d     Document Type: Article
Times cited : (7)

References (87)
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    • Oligo(ethylene glycol) (OEG) is also referred to as oligo(oxyethylene), oligo(ethylene oxide).
    • Oligo(ethylene glycol) (OEG) is also referred to as oligo(oxyethylene), oligo(ethylene oxide).
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    • (b) Derewenda, Z. S. Method, 2004, 34, 354-363.
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    • 1H NMR spectrum indicates that 7a is still present (5.3 (br s, CONH)). The deprotection of the N-trifluoroacetyl group with 1M NaOH was sluggish; see
    • 1H NMR spectrum indicates that 7a is still present (5.3 (br s, CONH)). The deprotection of the N-trifluoroacetyl group with 1M NaOH was sluggish; see: Rosso, V. W.; Pazdan, J. L.; Venit, J. J. Org. Proc. Res. Dev. 2001, 5, 294-298.
    • (2001) J. Org. Proc. Res. Dev. , vol.5 , pp. 294-298
    • Rosso, V.W.1    Pazdan, J.L.2    Venit, J.3
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    • 0031038658 scopus 로고    scopus 로고
    • 2O/MeOH (see ref 30b). Nonetheless, Kudzin et al. reported, that NaOMe-mediated deprotection is not effective due to the formation of stable amidate salts; see: Kudzin, Z. H.; Łyźwa, P.; Łuczak, J.; Andrijewski, G.
    • 2O/MeOH (see ref 30b). Nonetheless, Kudzin et al. reported, that NaOMe-mediated deprotection is not effective due to the formation of stable amidate salts; see: Kudzin, Z. H.; Łyźwa, P.; Łuczak, J.; Andrijewski, G. Synthesis 1997, 44-46.
    • (1997) Synthesis , pp. 44-46
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    • In NMR spectra characteristic peaks are observed (see the Supporting Information).
    • In NMR spectra characteristic peaks are observed (see the Supporting Information).
  • 66
    • 77949807864 scopus 로고    scopus 로고
    • The structure of this compound, was analyzed by 2D NMR, IR, and ESI-MS as well (see the Supporting Information).
    • The structure of this compound, was analyzed by 2D NMR, IR, and ESI-MS as well (see the Supporting Information).
  • 68
    • 77949849377 scopus 로고    scopus 로고
    • The structure of this compound was analyzed by 2D NMR, IR, and ESI-MS as well (see the Supporting Information).
    • The structure of this compound was analyzed by 2D NMR, IR, and ESI-MS as well (see the Supporting Information).
  • 70
    • 77949799708 scopus 로고    scopus 로고
    • The structure of this compound was analyzed by 2D NMR, IR, and ESI-MS as well see the Supporting Information.
    • (a) The structure of this compound was analyzed by 2D NMR, IR, and ESI-MS as well (see the Supporting Information.
  • 71
    • 77949798695 scopus 로고    scopus 로고
    • The "tacn"-OEG-alkene was further thioacetylated (AcSH, AIBN). Subsequent smooth deprotection of formyl and acetyl groups was performed under acidic conditions (see the Supporting Information).
    • (b) The "tacn"-OEG-alkene was further thioacetylated (AcSH, AIBN). Subsequent smooth deprotection of formyl and acetyl groups was performed under acidic conditions (see the Supporting Information).


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