Citation: CHENG Fang, WANG Han-Qi, XU Kuang, HE Wei. Preparation and Characterization of Dithiocarbamate Based Carbohydrate Chips[J]. Acta Physico-Chimica Sinica, ;2017, 33(2): 426-434. doi: 10.3866/PKU.WHXB201609291 shu

Preparation and Characterization of Dithiocarbamate Based Carbohydrate Chips

CHENG Fang ^1,2, ,
WANG Han-Qi ^1,2 ,
XU Kuang ^1,2 ,
HE Wei ³

1.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, Liaoning Province, P. R. China;
2.
School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116023, Liaoning Province, P. R. China;
3.
School of Chemical Engineering, Dalian University of Technology, Dalian 116023, Liaoning Province, P. R. China

Received Date: 12 August 2016
Revised Date: 28 September 2016

Fund Project: The project was supported by the National Natural Science Foundation of China (21104008, 21231003), Fundamental Research Funds for the Central Universities, China (DUT16RC(3)019) and Recruitment Program of Global Youth Experts, China.

Carbohydrates chips are powerful tools for quantitatively studying protein-carbohydrate interactions. Typically, carbohydrate chips are prepared using the self-assembly of carbohydrate thiol/disulfide, which always requires multiple hydroxyl group protection/deprotection steps resulting low conversion in the preparation. In this paper, a kind of carbohydrate derivatives containing dithiocarbamate (DTC) group was synthesized through a two-step reaction to prepare self-assembled monolayers presenting carbohydrate (glycol-DTC SAMs). The glycol-DTC SAMs was characterized using X-ray photoelectron spectroscopy (XPS) and the protein binding activity was quantitatively analysized using surface plasma resonance (SPR) and enzyme linked lectin assay (ELLA). By mixed self-assembly of carbohydrate dithiocarbamate and sarcosine dithiocarbamate, Glycol-DTC SAMs with different glucose density were prepared. The protein binding kinetics was monitored in real time and the thermodynamics was calculated. Interestingly, a 1:1 binding of concanavalin A (Con A) was obtained on the SAMs prepared in solution containing 1% glucose-DTC, as the dissociation constant (K_d) was calculated to be (39.10±0.12) μmol·L^-1. A 1:2 binding of Con A was obtained on the SAMs prepared in solutions containing >2% glucose-DTC, as the K_d was calculated to be (1.17±0.18) μmol·L^-1. By simply mixed selfassembly, multivalent binding of Con A can be realized and separate kinetic parameters can be obtained. Our work would promote the study of protein-carbohydrate interactions and be helpful for revealing the relevant biological progress.
- Carbohydrate-protein interaction,
- Dithiocarbamate,
- Multivalent adsorption,
- Thermodynamics,
- Kinetics,
- SAM
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