1.Synthesis of glycosyl amino acids by light-induced coupling of photoreactive amino acids with glycosylamines and 1-C-aminomethyl glycosides.
Simo O1, Lee VP, Davis AS, Kreutz C, Gross PH, Jones PR, Michael K. Carbohydr Res. 2005 Mar 21;340(4):557-66.
The glycosylamines of O-acetyl-protected GlcNAc and chitobiose, as well as two partially unprotected 1-C-aminomethyl glucosides, were photochemically coupled with orthogonally protected N-aspartyl-5-bromo-7-nitroindoline derivatives. The reactions proceeded under neutral conditions by irradiation with near-UV light. The glycosyl asparagines with N- or C-glycosyl linkages were afforded in 60-85% yield on a 10-70 mg scale. Moreover, the ability of a highly photoreactive N-glutamyl-4-methoxy-7-nitroindoline derivative to acylate amino saccharides was tested. Upon irradiation in the presence of a dimeric 1-C-aminomethyl glycoside, or a glycosylamine, the corresponding glycosyl glutamines were obtained in 50% and 30% yield, respectively. Preparations of the photoreactive aspartates and the 1-C-aminomethyl glycosides are also described.
2.Optically induced linking of protein and nanoparticles to gold surfaces.
Moth-Poulsen K1, Kofod-Hansen V, Kamounah FS, Hatzakis NS, Stamou D, Schaumburg K, Christensen JB. Bioconjug Chem. 2010 Jun 16;21(6):1056-61. doi: 10.1021/bc900561m.
Attachment of molecules and proteins to surfaces is of great interest for the development of a large variety of applications. We present herein a novel approach to efficiently couple a molecule of choice to biological building blocks. We synthesized and employed a new derivative of 5-bromo-7-nitroindoline to attach nucleophilic molecules and proteins to gold surfaces by photochemical activation. The reaction can be seen as a photoactivated alternative to the activated ester type chemistries that are commonly used to attach proteins or molecules to surfaces. We characterize the reaction by UV-vis and NMR spectroscopy, and as test of principle experiment, we show that we can attach proteins to surfaces and demonstrate that we can functionalize gold nanoparticles by this optically induced cross-linking reaction.
