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Volumn 15, Issue 3, 2009, Pages 710-725

Ferrocene-carbohydrate conjugates as electrochemical probes for molecular recognition studies

Author keywords

Click chemistry; Ferrocene; Glycoconjugates; Molecular sensors; Voltammetry

Indexed keywords

BINDING ENERGY; COPPER; GLUCOSE; IRON COMPOUNDS; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; PARAMETER ESTIMATION; SENSORS; SUGARS; THERMODYNAMIC STABILITY; VOLTAMMETRY;

EID: 58449108814     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800927     Document Type: Article
Times cited : (76)

References (81)
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  • 2
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    • Eds, A. Varki, R. Cummings, J. Esko, H. Freeze, G. Hart, J. Marth, Cold Spring Harbor Laboratory Press, New York
    • b) A. Varki in Essentials of Glycobiology (Eds.: A. Varki, R. Cummings, J. Esko, H. Freeze, G. Hart, J. Marth), Cold Spring Harbor Laboratory Press, New York, 1999.
    • (1999) Essentials of Glycobiology
    • Varki, A.1
  • 31
  • 38
    • 0037099395 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 2596-2599;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 2596-2599
  • 49
    • 58449127638 scopus 로고    scopus 로고
    • While performing the electrochemical experiments, we discovered that dilactosyl compound 39 was not pure enough. DPV experiment for 39 showed two oxidation peaks due to the presence of an impurity that we could confirm by HPLC analysis. All attempts carried out by us to purify compound 39 by preparative HPLC failed. We investigated the origin of the impurity and we have concluded that it comes from the synthesis of propargyl lactoside 22, which was obtained from the reaction of per-O-acetyl lactose and propargyl alcohol in the presence of BF3·OEt2 as catalyst see Experimental Section in ref, 32b, Under those reaction conditions glycoside 22 is formed together with the a-anomer as a minor product, both anomers having the same Rf value by TLC. The presence of the impurity was not detected by 1H NMR spectroscopy at first, but a long-time accumulation of a 13C NMR experiment allowed us to o
    • 13C NMR experiment allowed us to observe the presence of the presumably anomeric carbon of the α anomer. However, the synthesis and purification of compound 25 were not affected by the slight impurity of the starting material as it was later confirmed by the electrochemical experiments.
  • 74
    • 58449101687 scopus 로고    scopus 로고
    • f value used is the one determined through Equation (5).
    • f value used is the one determined through Equation (5).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.