Synthesis and characterization of a photoactivatable glycoaryldiazirine for surface glycoengineering

被引:29
作者
Chevolot, Y [1 ]
Bucher, O
Léonard, D
Mathieu, HJ
Sigrist, H
机构
[1] Ecole Polytech Fed Lausanne, LMCH, Dept Mat, CH-1015 Lausanne, Switzerland
[2] Ctr Suisse Elect & Microtech SA, CH-2007 Neuchatel, Switzerland
关键词
D O I
10.1021/bc980050h
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Biological systems make considerable use of specific molecular interactions. Many biomolecules involved in biorecognition are glycosylated, the carbohydrate moiety playing an essential role. Controlled surface glycoengineering is thus of crucial importance in biosensing, cell guidance, and biomedical applications. This study describes the synthesis of an aryldiazirine-derivatized galactose and the functionalization of surfaces by carbohydrates using photochemical immobilization techniques. A photoactivatable glycosylated reagent was synthesized by addition of thiogalactopyranose to the maleimide group of N-[m-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-4-maleimidobutyramide (MAD) to give N-[m-[3-(trifluoromethyl) diazirin-3-yl]phenyl]-4-[3-thio(1-D-galactopyranosyl)succinimidyl]butyramide (MAD-Gal). The structure of the newly synthesized molecule was confirmed by UV spectroscopy, photoactivation, H-1 NMR, and C-13 NMR. MAD-Gal was immobilized on thin diamond films by photoactivation of the diazirine function (350 nm). Surface modification was investigated by XPS (X-ray photoelectron spectroscopy) and ToF-SIMS (time-of-flight secondary ion mass spectrometry). Imaging ToF-SIMS was applied to detect glycopatterns generated by mask-assisted lithography.
引用
收藏
页码:169 / 175
页数:7
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