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NMR studies of micelle forming model glycolipids

University of British Columbia

The work described herein falls into three major categories: synthesis of model glycolipids, NMR studies on'model glycolipid'micelles, and application of 2D-NMR spectroscopy in spectral assignment. Three synthetic routes, namely the glycosidation reaction, reductive amination reaction, and amide bond formation have been investigated in relation to their efficiency and convenience in coupling carbohydrates with aliphatic chains. The reaction of amide bond formation was found to be a superior method over the others for the preparation of long alkyl chain derivatives. ¹H-NMR spectroscopy has been utilized to study and detect the micelle formation by the model glycolipids. The studies described illustrate that the ¹H spin-lattice relaxation rate (R-₁) is well suited for the determination of critical micelle concentration providing it is sufficiently high. The contrasting behaviour of R-₁ of the anomeric proton (H-1) of n-octyl β-D-glucoside in relation to that of H-2 and w-CH₃ upon micellization, has been tentatively attributed to the conformational changes accompanying micelle formation. The observed upfield shift of the ¹³C resonances of the alkyl chain has been explained as being due to the increased proportion of trans conformers in the micellar state. The question of the downfield ¹³C shift observed for the sugar resonances has been discussed. Study of N-alkyllactobionamides with ¹H-NMR proved to be difficult due to their extremely low critical micelle concentrations. Application of 2D J-resolved spectroscopy and spin-echo correlated spectroscopy (SECSY) in spectral assignment of unprotected sugar derivatives has been demonstrated. Using above techniques, complete assignment of the sugar region of n-octyl β-D-glucoside and N-hexyllactobionamide has been achieved.

Text

2010-03-31

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http://hdl.handle.net/2429/23222

Chemistry

University of British Columbia

Graduate