Electronic Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2012
Supplementary Information Unexpected chiral induction from achiral cationic polythiophene aggregates and its application to the sugar pattern recognition Tomohiro Shiraki,a,b Arnab Dawnc, Youichi Tsuchiya a,b, Tatsuhiro Yamamoto a,b and Seiji Shinkai*a,c,d
a
Nanotechnology Laboratory, Institute of Systems, Information Technologies and Nanotechnologies (ISIT), 203-1 Moto-oka, Nishi-ku, Fukuoka, 819-0385, Japan. b
Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan.
c
Institute for Advanced Study, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan.
d
Department of Nanoscience, Faculty of Engineering, Sojo University, 4-22-1 Ikeda, Kumamoto 8600082, Japan. Fax: +81-92-805-3814; Tel: +81-92-805-3810; E-mail:
[email protected]
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Electronic Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2012
Materials D-Galactose, D-mannose, D-talose, L-fructose, D-sorbose, L-arabinose, L-lyxose, Dxylose, L-sorbose, D-tagatose, D-lyxose, L-xylose, 1-methyl--D-galactopyranoside, 1-methyl-D-glucopyranoside, cholic acid, N-(tert-butoxycarbonyl)-glutamic acid (BOC-Glu (D- or Ltype)) and N-(tert-butoxycarbonyl)-alanine (BOC-Ala (D- or L- type)) were purchased from Tokyo Chemical Industry Co., Ltd. D-Allose, D-glucose, L-galactose, L-allose, L-glucose, Lmannose, D-arabinose, L-fucose, 2-deoxygalactose and 3-methyl-D-glucose were bought from Sigma-Aldrich Co. D-Fructose and D-fucose were received from Wako Pure Chemical Industries, Ltd. All reagents were used without further purification. PT1 was synthesized according to our published papers.S1
Instruments UV/Vis absorption was recorded on a JASCO V-670 spectrophotometer with a Peltier type thermostatic cell holder. CD spectra were recorded on a JASCO J-720WI spectropolarimeter with a thermostatic bath. The path length of the quartz cells was 1 cm. Specific optical rotation [] was measured by using the JASCO J-720WI with conditions of [sugars] = 0.018 g/100 cm3, L = 1 dm, = 589.5 nm and chloroform containing 5 vol.% MeOH and 5 vol.% DMSO. All measurements were performed at 25 C.
Sample Preparation Stock solutions of PT1 in methanol (4 mM) and a sugar in DMSO (various concentrations) were prepared. At first, 50 L of the PT1 solution and 50 L of the sugar solution were mixed. To the mixture, 900 L of chloroform was poured, the final composition being 90 vol.% chloroform, 5 vol.% MeOH and 5 vol.% DMSO. The mixed solutions were measured after leaving 4 hours at 25 C.
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Electronic Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2012
Fig. S1 UV/vis spectra of PT1‒D-galactose mixture (solid line) and PT1‒L-galactose mixture (dotted line) in chloroform containing 5 vol.% MeOH and 5 vol.% DMSO and PT1 itself (dashed line) in MeOH; [PT1] = 0.20 mM, [galactose] = 1.0 mM.
Fig. S2 CD spectra of PT1/sugar mixtures using D-type or L-type isomer (solid line and dotted line, respectively); [PT1] = 0.20 mM, [sugars] = 1.0 mM, chloroform containing 5 vol.% MeOH and 5 vol.% DMSO.
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Electronic Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2012
Fig. S3 CD spectra of PT1 itself in MeOH and PT1 itself, PT1‒D -galactose mixture and PT1‒L galactose mixture in the mixed solvent of 50 vol.% MeOH and 50 vol.% DMSO; [PT1] = 0.20 mM, [sugars] = 1.0 mM.
Fig. S4 CD spectra of mixtures of PT1 and sugars bearing four OH groups; [PT1] = 0.20 mM, [sugars] = 1.0 mM, chloroform containing 5 vol.% MeOH and 5 vol.% DMSO.
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Electronic Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2012
Fig. S5 CD spectra of mixtures of PT1 and other nature-originated molecules (cholic acid, BOCGlu and BOC-Ala); [PT1] = 0.20 mM, [added molecules] = 1.0 mM, chloroform containing 5 vol.% MeOH and 5 vol.% DMSO.
Reference S1 (a) C. Li, M. Numata, A.-H. Bae, K. Sakurai and S. Shinkai, J. Am. Chem. Soc., 2005, 127, 4548; (b) T. Shiraki, A. Dawn, Y. Tsuchiya and S. Shinkai, J. Am. Chem. Soc., 2010, 132, 13928.
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