Solid phase synthesis of functionalised SAM-forming alkanethiol-oligoethyleneglycols
We present an efficient solid phase synthesis methodology that provides easy access to a range of functionalised long-chain alkanethiol-oligoethyleneglycols that form well-defined self-assembled monolayers on gold and are compatible with pre- or post-assembly conjugation of (bio)molecules. We demons...
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| Published in | Journal of materials chemistry. B, Materials for biology and medicine Vol. 2; no. 24; pp. 3741 - 3744 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
28.06.2014
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| Subjects | |
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| Abstract | We present an efficient solid phase synthesis methodology that provides easy access to a range of functionalised long-chain alkanethiol-oligoethyleneglycols that form well-defined self-assembled monolayers on gold and are compatible with pre- or post-assembly conjugation of (bio)molecules. We demonstrate the versatility of our synthetic route by synthesising LCAT-OEGs with a range of functional moieties, including peptides, electro-active redox groups, chemical handles for post-assembly conjugation of (bio)molecules, and demonstrate the application of our LCAT-OEG monolayers in immunosensing, where they show good biocompatibility with minimal biofouling. |
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| AbstractList | We present an efficient solid phase synthesis methodology that provides easy access to a range of functionalised long-chain alkanethiol–oligoethyleneglycols that form well-defined self-assembled monolayers on gold and are compatible with pre- or post-assembly conjugation of (bio)molecules. We demonstrate the versatility of our synthetic route by synthesising LCAT–OEGs with a range of functional moieties, including peptides, electro-active redox groups, chemical handles for post-assembly conjugation of (bio)molecules, and demonstrate the application of our LCAT–OEG monolayers in immunosensing, where they show good biocompatibility with minimal biofouling. |
| Author | Critchley, Kevin Nowak, Dominika Guillorit, Mathieu Johnson, Steven Bon, Robin S Pukenas, Laurynas Wälti, Christoph Murray, James Azhar, Rizuan |
| AuthorAffiliation | c School of Electronic and Electrical Engineering, University of Leeds, UK e Department of Electronics, University of York, Heslington York, YO10 5DD, UK b Astbury Centre for Structural Molecular Biology, University of Leeds, UK d School of Physics and Astronomy, University of Leeds, UK a School of Chemistry, University of Leeds, LS2 9JT, UK |
| AuthorAffiliation_xml | – name: d School of Physics and Astronomy, University of Leeds, UK – name: b Astbury Centre for Structural Molecular Biology, University of Leeds, UK – name: a School of Chemistry, University of Leeds, LS2 9JT, UK – name: c School of Electronic and Electrical Engineering, University of Leeds, UK – name: e Department of Electronics, University of York, Heslington York, YO10 5DD, UK |
| Author_xml | – sequence: 1 givenname: James surname: Murray fullname: Murray, James organization: School of Chemistry, University of Leeds, LS2 9JT, UK ; Astbury Centre for Structural Molecular Biology, University of Leeds, UK – sequence: 2 givenname: Dominika surname: Nowak fullname: Nowak, Dominika organization: Astbury Centre for Structural Molecular Biology, University of Leeds, UK ; School of Electronic and Electrical Engineering, University of Leeds, UK – sequence: 3 givenname: Laurynas surname: Pukenas fullname: Pukenas, Laurynas organization: Astbury Centre for Structural Molecular Biology, University of Leeds, UK ; School of Physics and Astronomy, University of Leeds, UK – sequence: 4 givenname: Rizuan surname: Azhar fullname: Azhar, Rizuan organization: Department of Electronics, University of York, Heslington York, YO10 5DD, UK – sequence: 5 givenname: Mathieu surname: Guillorit fullname: Guillorit, Mathieu organization: School of Chemistry, University of Leeds, LS2 9JT, UK – sequence: 6 givenname: Christoph surname: Wälti fullname: Wälti, Christoph organization: School of Electronic and Electrical Engineering, University of Leeds, UK – sequence: 7 givenname: Kevin surname: Critchley fullname: Critchley, Kevin organization: Astbury Centre for Structural Molecular Biology, University of Leeds, UK ; School of Physics and Astronomy, University of Leeds, UK – sequence: 8 givenname: Steven surname: Johnson fullname: Johnson, Steven organization: Department of Electronics, University of York, Heslington York, YO10 5DD, UK – sequence: 9 givenname: Robin S surname: Bon fullname: Bon, Robin S organization: School of Chemistry, University of Leeds, LS2 9JT, UK ; Astbury Centre for Structural Molecular Biology, University of Leeds, UK |
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| CitedBy_id | crossref_primary_10_1016_j_sbsr_2015_09_004 crossref_primary_10_1021_acs_chemmater_8b00377 crossref_primary_10_1080_00958972_2019_1655550 crossref_primary_10_1038_ncomms12769 crossref_primary_10_1016_j_ejmech_2019_111563 crossref_primary_10_1186_s43088_020_00083_7 |
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| References | Bouzide (C4TB00573B-(cit13)/*[position()=1]) 2002; 4 Laurent (C4TB00573B-(cit5c)/*[position()=1]) 2008; 9 Tam-Chang (C4TB00573B-(cit12a)/*[position()=1]) 1995; 11 Svedhem (C4TB00573B-(cit12b)/*[position()=1]) 1999; 15 Cassie (C4TB00573B-(cit18)/*[position()=1]) 1944; 40 Góes (C4TB00573B-(cit19)/*[position()=1]) 2012; 28 Prats-Alfonso (C4TB00573B-(cit6b)/*[position()=1]) 2006; 62 Samanta (C4TB00573B-(cit5b)/*[position()=1]) 2011; 40 Pheeney (C4TB00573B-(cit17)/*[position()=1]) 2012; 28 Bertin (C4TB00573B-(cit8)/*[position()=1]) 2010; 12 Tolstyka (C4TB00573B-(cit9)/*[position()=1]) 2013; 14 Love (C4TB00573B-(cit1)/*[position()=1]) 2005; 105 Booth (C4TB00573B-(cit6a)/*[position()=1]) 2001; 57 Ryan (C4TB00573B-(cit11)/*[position()=1]) 2004; 20 Houseman (C4TB00573B-(cit7b)/*[position()=1]) 1998; 63 Derda (C4TB00573B-(cit6c)/*[position()=1]) 2007; 23 Svedhem (C4TB00573B-(cit14)/*[position()=1]) 2001; 66 Kang (C4TB00573B-(cit16)/*[position()=1]) 2009; 81 Kleinert (C4TB00573B-(cit10)/*[position()=1]) 2004; 18 Li (C4TB00573B-(cit5a)/*[position()=1]) 2007; 23 Zhou (C4TB00573B-(cit3)/*[position()=1]) 2011; 7 Prats-Alfonso (C4TB00573B-(cit7a)/*[position()=1]) 2013; 7 Jonkheijm (C4TB00573B-(cit2a)/*[position()=1]) 2008; 47 Bartra (C4TB00573B-(cit15)/*[position()=1]) 1990; 46 Cole (C4TB00573B-(cit20)/*[position()=1]) 1997; 43 Zaccari (C4TB00573B-(cit2b)/*[position()=1]) 2014; 30 Prime (C4TB00573B-(cit4)/*[position()=1]) 1991; 252 |
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| Snippet | We present an efficient solid phase synthesis methodology that provides easy access to a range of functionalised long-chain alkanethiol-oligoethyleneglycols... We present an efficient solid phase synthesis methodology that provides easy access to a range of functionalised long-chain alkanethiol–oligoethyleneglycols... |
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| SubjectTerms | Alkanes Biocompatibility Biology Compatibility Conjugation Handles Monolayers Solid phase synthesis |
| Title | Solid phase synthesis of functionalised SAM-forming alkanethiol-oligoethyleneglycols |
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