Significance of the amide functionality on DOPA-based monolayers on gold

The adhesive proteins secreted by marine mussels contain an unusual amino acid, 3,4-dihydroxyphenylalanine (DOPA), that is responsible for the cohesive and adhesive strength of this natural glue and gives mussels the ability to attach themselves to rocks, metals, and plastics. Here we report a detai...

Ausführliche Beschreibung

Bibliographische Detailangaben
Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1985. - 28(2012), 49 vom: 11. Dez., Seite 16900-8
1. Verfasser: Rībena, Dina (VerfasserIn)
Weitere Verfasser: Alekseev, Alexander, van Asselen, Otto, Mannie, Gilbère J A, Hendrix, Marco M R M, van der Ven, Leendert G J, Sommerdijk, Nico A J M, de With, Gijsbertus
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2012
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article Adhesives Amides Catechols N-stearoyl-dopamine Proteins Stearates Water 059QF0KO0R Dihydroxyphenylalanine mehr... 63-84-3 Gold 7440-57-5 Dopamine VTD58H1Z2X
LEADER 01000caa a22002652 4500
001 NLM222676159
003 DE-627
005 20250214154231.0
007 cr uuu---uuuuu
008 231224s2012 xx |||||o 00| ||eng c
024 7 |a 10.1021/la303308m  |2 doi 
028 5 2 |a pubmed25n0742.xml 
035 |a (DE-627)NLM222676159 
035 |a (NLM)23157706 
040 |a DE-627  |b ger  |c DE-627  |e rakwb 
041 |a eng 
100 1 |a Rībena, Dina  |e verfasserin  |4 aut 
245 1 0 |a Significance of the amide functionality on DOPA-based monolayers on gold 
264 1 |c 2012 
336 |a Text  |b txt  |2 rdacontent 
337 |a ƒaComputermedien  |b c  |2 rdamedia 
338 |a ƒa Online-Ressource  |b cr  |2 rdacarrier 
500 |a Date Completed 20.05.2013 
500 |a Date Revised 21.11.2013 
500 |a published: Print-Electronic 
500 |a Citation Status MEDLINE 
520 |a The adhesive proteins secreted by marine mussels contain an unusual amino acid, 3,4-dihydroxyphenylalanine (DOPA), that is responsible for the cohesive and adhesive strength of this natural glue and gives mussels the ability to attach themselves to rocks, metals, and plastics. Here we report a detailed structural and spectroscopic investigation of the interface between N-stearoyldopamine and a single-crystalline Au(111) model surface and an amide-absent molecule, 4-stearylcatechol, also on Au(111), with the aim of understanding the role of the amide functionality in the packing, orientation, and fundamental interaction between the substrate and the monolayer formed from an aqueous environment by the Langmuir-Blodgett technique. The organization of monolayers on gold was observed directly and studied in detail by X-ray photoelectron spectroscopy (XPS), contact angle measurements (CA), surface-enhanced Raman spectroscopy (SERS), infrared reflection-absorption spectroscopy (IRRAS), and atomic force microscopy (AFM). Our study shows that within the monolayer the catecholic oxygen atoms are coordinated to the gold surface, having a more perpendicular orientation with respect to the aromatic ring and the apparently tilted alkyl chains, whereas the amide functionality stabilizes the monolayer that is formed 
650 4 |a Journal Article 
650 7 |a Adhesives  |2 NLM 
650 7 |a Amides  |2 NLM 
650 7 |a Catechols  |2 NLM 
650 7 |a N-stearoyl-dopamine  |2 NLM 
650 7 |a Proteins  |2 NLM 
650 7 |a Stearates  |2 NLM 
650 7 |a Water  |2 NLM 
650 7 |a 059QF0KO0R  |2 NLM 
650 7 |a Dihydroxyphenylalanine  |2 NLM 
650 7 |a 63-84-3  |2 NLM 
650 7 |a Gold  |2 NLM 
650 7 |a 7440-57-5  |2 NLM 
650 7 |a Dopamine  |2 NLM 
650 7 |a VTD58H1Z2X  |2 NLM 
700 1 |a Alekseev, Alexander  |e verfasserin  |4 aut 
700 1 |a van Asselen, Otto  |e verfasserin  |4 aut 
700 1 |a Mannie, Gilbère J A  |e verfasserin  |4 aut 
700 1 |a Hendrix, Marco M R M  |e verfasserin  |4 aut 
700 1 |a van der Ven, Leendert G J  |e verfasserin  |4 aut 
700 1 |a Sommerdijk, Nico A J M  |e verfasserin  |4 aut 
700 1 |a de With, Gijsbertus  |e verfasserin  |4 aut 
773 0 8 |i Enthalten in  |t Langmuir : the ACS journal of surfaces and colloids  |d 1985  |g 28(2012), 49 vom: 11. Dez., Seite 16900-8  |w (DE-627)NLM098181009  |x 1520-5827  |7 nnns 
773 1 8 |g volume:28  |g year:2012  |g number:49  |g day:11  |g month:12  |g pages:16900-8 
856 4 0 |u http://dx.doi.org/10.1021/la303308m  |3 Volltext 
912 |a GBV_USEFLAG_A 
912 |a SYSFLAG_A 
912 |a GBV_NLM 
912 |a GBV_ILN_22 
912 |a GBV_ILN_350 
912 |a GBV_ILN_721 
951 |a AR 
952 |d 28  |j 2012  |e 49  |b 11  |c 12  |h 16900-8