Document Detail

Self-assembled monolayers with latent aldehydes for protein immobilization.
MedLine Citation:
PMID:  17226979     Owner:  NLM     Status:  MEDLINE    
Aldehyde functions are widely used for immobilization of biomolecules on glass surfaces but have found little attention for biofunctionalization of self-assembled monolayers (SAMs) on gold, due to interference between thiol and aldehyde functions. This problem was recently solved by synthesis of an alkanethiol that carried a vicinal diol group [Jang et al. (2003) Nano Lett. 3, 691-694]. The latter served as a latent aldehyde function that was unmasked by short exposure of the vicinal diol-terminated SAM to aqueous periodate. However, the synthesis of the new vicinal diol-terminated alkane thiol was time-consuming and had an overall yield of approximately 3.5%. In the present study, a general modular strategy was introduced by which SAM components with vicinal diol functions were rapidly synthesized with high yield: this was accomplished by amide bond formation between a SAM-forming carboxylic acid (exemplified by lipoic acid and 16-mercaptohexadecanoic acid) with 3-aminopropane-1,2-diol, using suitable protecting groups. The disulfide or free thiol group afforded SAM formation on gold and, after periodate oxidation of the vicinal diol functions, proteins were covalently bound via their lysine residues. At 1 mg/mL protein concentration, complete surface coverage was reached within minutes. No further protein was bound by nonspecific adsorption, but cognate proteins were specifically bound with high capacity. Pyrogallol-O-hexadecanoic acid and 10-undecenoic acid were also coupled with 3-aminopropane-1,2-diol by amide bond formation, thereby producing latent aldehyde-containing SAM components for metal oxides and hydrogen-terminated silicon, respectively, to show the general usefulness of the new synthetic design.
Christoph D Hahn; Christa Leitner; Theo Weinbrenner; Robert Schlapak; Ali Tinazli; Robert Tampé; Bernd Lackner; Christian Steindl; Peter Hinterdorfer; Hermann J Gruber; Martin Hölzl
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioconjugate chemistry     Volume:  18     ISSN:  1043-1802     ISO Abbreviation:  Bioconjug. Chem.     Publication Date:    2007 Jan-Feb
Date Detail:
Created Date:  2007-01-17     Completed Date:  2007-02-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9010319     Medline TA:  Bioconjug Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  247-53     Citation Subset:  IM    
Institute of Biophysics and Institute of Organic Chemistry, University of Linz, Altenberger Strasse 69, A-4040 Linz, Austria.
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MeSH Terms
Aldehydes / chemistry*
Molecular Structure
Oxides / chemistry
Protein Array Analysis / methods*
Proteins / chemistry*
Silicon / chemistry
Thioctic Acid / chemistry
Reg. No./Substance:
0/Aldehydes; 0/Oxides; 0/Proteins; 62-46-4/Thioctic Acid; 7440-21-3/Silicon

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