Synthesis and Surface-Spectroscopic Characterization of Photoisomerizable glyco-SAMs on Au(111)

被引:22
作者
Chandrasekaran, Vijayanand [1 ]
Jacob, Hanne [2 ]
Petersen, Finn [2 ]
Kathirvel, Ketheeswari [2 ]
Tuczek, Felix [2 ]
Lindhorst, Thisbe K. [1 ]
机构
[1] Univ Kiel, Otto Diels Inst Organ Chem, D-24118 Kiel, Germany
[2] Univ Kiel, Inst Inorgan Chem, D-24118 Kiel, Germany
关键词
azobenzene; glycosides; photoswitching; self-assembly; IR spectroscopy; SELF-ASSEMBLED MONOLAYERS; CARBOHYDRATE-PROTEIN INTERACTIONS; MONO LAYERS; AZOBENZENE; BINDING; CONSTRUCTION; FABRICATION; MICROARRAYS; ADSORPTION; THIOLS;
D O I
10.1002/chem.201402075
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photoisomerizable glyco-SAMs (self-assembled monolayers), utilizing synthetic azobenzene glycoside derivatives were fabricated. The ultimate goal of this project is to assay the influence of the 3D arrangement of sugar ligands on cell adhesion, and eventually make cell adhesion photo-switchable. However, it is a prerequisite for any biological study on the spatial conditions of carbohydrate recognition, that photoisomerization of the surface molecules can be verified. Here, we employed IRRAS and XPS to spectroscopically characterize glyco-SAMs. In particular and unprecedented to date, we prove reversible E -> Z -> E isomerization of azobenzene glycoside-terminated SAMs.
引用
收藏
页码:8744 / 8752
页数:9
相关论文
共 68 条
[1]  
[Anonymous], [No title captured], Patent No. 0901
[2]  
[Anonymous], CASA XPS
[3]  
[Anonymous], 2009, ANGEW CHEM
[4]  
[Anonymous], INFRARED RECLECTION
[5]  
[Anonymous], ANGEW CHEM
[6]   Kinetically stable, flat-lying thiolate monolayers [J].
Badin, Mihaela G. ;
Bashir, Asif ;
Krakert, Simone ;
Strunskus, Thomas ;
Terfort, Andreas ;
Woell, Christof .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (20) :3762-3764
[7]  
Ban L., 2008, ANGEW CHEM, V120, P3444
[8]   On-chip synthesis and label-free assays of oligosaccharide arrays [J].
Ban, Lan ;
Mrksich, Milan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3396-3399
[9]   Chemical glycobiology [J].
Bertozzi, CR ;
Kiessling, LL .
SCIENCE, 2001, 291 (5512) :2357-2364
[10]   SAMs on Gold Derived from the Direct Adsorption of Alkanethioacetates Are Inferior to Those Derived from the Direct Adsorption of Alkanethiols [J].
Bethencourt, Mathilde I. ;
Srisombat, La-ongnuan ;
Chinwangso, Pawilai ;
Lee, T. Randall .
LANGMUIR, 2009, 25 (03) :1265-1271