In-situ functionalized fluorescent nanoparticles for efficient receptor coupling. Supplementary Material
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- Beatrix Morgan
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1 In-situ functionalized fluorescent nanoparticles for efficient receptor coupling Chemistry Department, Faculty of Science, University of Malaya, Lembah Pantai, Kuala Lumpur, Malaysia Supplementary Material Synthesis of surface modification reagents and model receptor General synthesis procedures A) Monopropargylation of ethylene glycol oligomers (2).[1] To a solution of diol 1 (6 equiv.) in THF was added NaH (60% w/w in mineral oil) (1 equiv). After stirring for 15 min, propargyl bromide (80% in toluene) (1 equiv) was added slowly. Stirring was continued for 8 h, before the solvent was evaporated. The resulting mixture was extracted with CH 2 Cl 2 against water. The organic phase was dried over MgSO 4 and concentrated under vacuum. The residue was taken up in MeCN and extracted with hexane. The acetonitrile phase was evaporated and the crude 2 was purified by chromatography using hexane and ethyl acetate. B) α-bromo-α-deoxy-ω-o-propargyl-ethylene oxide oligomers (3).[2] A solution of the ethylene glycol mono-propargyl ether, 2, (2 equiv) in CHCl 3 was cooled and PBr 3 (1 equiv) was added drop-wise at 0-5 C under stirring. The mixture was allowed to warm to room temperature and left for 8h, before water was added and the mixture was extracted with CH 2 Cl 2. The combined extracts were dried over anhydrous MgSO 4 and concentrated to dryness. The crude product was purified by column chromatography using hexane and EtOAc. C) Phosphonates (4).[3] Halide 3 (1 equiv) and triethyl phosphite (2 equiv) were heated to 150 C for 10 h. Excess reagent was evaporated in vacuum to give the phosphonic ester 4. D) Saponification of phosphonic esters.[4] To a solution of phosphonic ester 4(1 equiv) in CHCl 3 was added bromotrimethylsilane (5 equiv) and the mixture was kept for 24 h at room temperature. The solvent was evaporated in vacuum and the oily residue was dissolved in methanol. The reaction mixture was stirred at room temperature over night and subsequently concentrated to give the phosphonic acid 5. [1] Norberg, O.; Deng, L.; Yan, M.; Ramström, O., Photo-click immobilization of carbohydrates on polymersic surfaces A quick method to functionalize surfaces for biomolecular recognition studies. Bioconjugate Chem. 2009, 20, [2] Bo, Z.; Zhang, X.; Yi, X.; Yang, M.; Shen, J.; Rehn, Y.; Xi, S., The synthesis of dendrimers bearing alkyl chains and their behavior at air-water interface. Polymer Bulletin 1997, 38, [3] Deussen, H.-J.; Danielsen, S.; Breinholt, J.; Borchert, T.V., A novel biotinylated suicide inhibitor for directed molecular evolution of lipolytic enzymes. Bioorg. Med. Chem. 2000, 8, [4] Boduszek, B., Aminophosphonic acids bearing heterocyclic moiety. Part 4. Synthesis of 2-pyridyl and 4-pyridylmethyl- (amino)phosphonic acids. Phosphorus Sulfur and Silicon 1997, 122, / 12 -
2 E) Glycosylation of oligo-ethylene glycol monotosylates (9).[5] β-glucose pentaacetate, 8, (1 eqiuv) and ethylene glycol monotosylate, 7,[6] (1.1 equiv) were dissolved in CH 2 Cl 2 (~3.5 ml/mmol) and treated with BF 3 OEt 2 (1.5 equiv). The reaction was stirred at rt for 3 h and then washed with a sat. NaHCO 3 (aq) and water. The organic layer was dried over MgSO 4 and concentrated. The product was purified by column chromatography using Hex/EtOAc 2-3:1. F) Azidoethylene glycol glycosides (10). A solution of 9 (1 equiv) in DMF (~6 ml/mmol) was treated with NaN 3 (1.5 equiv) and stirred at 70 C over night. The solvent was then evaporated in vacuum and the remaining material was distributed between water and CH 2 Cl 2. The organic phase was dried over MgSO 4 and concentrated to provide NMR-pure 10. Diethylene glycol mono-propargyl ether (2a). Diethlyene glycol (26.10 g, 264 mmol) was reacted with NaH (1.6 g, 41 mmol) and propargyl bromide (4.85 g, 41 mmol) in THF (150 ml) according to general procedure A. Purification on silica with hexane/etoac 1:2 gave 1 as a colorless oil (3.4 g, 70 %). IR [KBr]: 3420 (OH), 2901, 2873 (CH), 2115 (C C) cm H NMR (400 MHz, CDCl 3 ): 4.11 (d, 2 H, CH 2 CCH), (m, 2 H, CH 2 OH), (m, 2 H, CH 2 OC 3 ), 3.61 (bs, 4 H, 2 EG-CH 2 ), 2.40 (t, CH); 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 70.14, 69.29, (3 EG-CH 2 ), (CH 2 OH), 58.0 (OCH 2 ). Triethylene glycol mono-propargyl ether (2b). Triethlyene glycol (36.94 g, 264 mmol) was reacted with NaH (1.6 g, 41 mmol) and propargyl bromide (4.85 g, 41 mmol) in THF (150 ml) according to general procedure A. Purification on silica with hexane/etoac 1:2 gave 2 as a colorless oil (3.54 g, 73 %). IR [KBr]: 3446 (OH), 2918, 2872, (CH), 2114 (C C) cm H NMR (400 MHz, CDCl 3 ): 4.17 (d~bs, 2 H, CH 2 CCH), (m, 2 H, CH 2 OH), 3.66, 3.63 (2 m c, 2 4 H, 2 2 EG-CH 2 ), (m, 2 H, CH 2 OC 3 ), (m, 12H, CH 2 O), 2.42 (t~bs, CH); 4 J propargyl ~2 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 72.39, 70.47, 70.21, 70.16, (5 EG-CH 2 ), (CH 2 OH), (OCH 2 ). Tetraethylene glycol mono-propargyl ether (2c). Tetraethlyene glycol (47.78 g, 264 mmol) was reacted with NaH (1.6 g, 41 mmol) and propargyl bromide (4.85 g, 41 mmol) in THF (200 ml) according to general procedure A. Purification on silica using hexane/etoac 1:3 gave 3 as a colorless oil (6.19 g, 65%). IR [KBr]: 3445 (OH), 2911, 2872 (CH), 2115 (C C) cm H NMR (400 MHz, CDCl 3 ): 4.11 (d, 2 H, CH 2 CCH), (m, 16 H, CH 2 O), 2.39 (t, CH); 4 J propargyl = 2.0 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 72.34, 70.32, 70.27, 70.23, 70.08, 70.02, (7 EG-CH 2 ), (CH 2 OH), (OCH 2 ). [5] Vill, V.; Thiem, J.; Fischer, B., Studies on liquid crystalline glycolipids. Liq. Cryst. 1986, 6, [6] Berowitz, P.T.; Baum, K., Reacions of 2-fluoro-2-nitro-1,3-propandiol. p-toluenesulfonates. J. Org. Chem. 1981, 46, / 12 -
3 9-Bromo-4,7-dioxa-1-nonyne (3a). Compound 2a (5.00 g, 34.7 mmol) was reacted according to general procedure B. Purification on silica with hexane/etoac 4:1 gave 3a as a yellow oil (5.81 g, 81 %). IR [KBr]: 2918, 2874 (CH), 2112 (C C) cm H NMR (400 MHz, CDCl 3 ): 4.15 (d, 2H, CH 2 CCH), 3.75 (t, 2 H, β=och 2 ), 3.64 (s, 4 H, EG-CH 2 ), 3.42 (t, 2 H, α=ch 2 Br), 2.42 (t, CH); 3 J α,β = 6.5, 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 70.96, 70.08, (3 EG-CH 2 ), (CH 2 CCH), (CH 2 Br). 12-Bromo-4,7,10-trioxa-1-dodecyne (3b). Compound 2b (6.00 g, 31.9 mmol) was reacted according to general procedure B. Purification on silica with hexane/etoac 3:1 gave 3b (6.00 g, 75 %) as yellow oil. IR [KBr]: 2871 (CH), 2115 (C C) cm H NMR (400 MHz, CDCl 3 ): 4.18 (d, 2 H, CH 2 CCH), 3.79 (t, 2 H, β=och 2 ), 3.68, 3.65 (2 m c, 2 4 H, EG-CH 2 ), 3.45 (t, 2 H, α=ch 2 Br), 2.42 (t, CH); 3 J α,β = 6.5, 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 71.09, 70.49, 70.40, 70.37, (5 EG-CH 2 ), (CH 2 CCH), (CH 2 Br). 15-Bromo-4,7,10,13-tetraoxa-1-pentadecyne (3c). Compound 2c (5.50 g, 23.7 mmol) was reacted according to general procedure B. Purification on silica with hexane/etoac 3:1 gave 3c as a yellow oil (5.45 g, 78%). IR [KBr]): 2871 (CH), 2114 (C C) cm H NMR (400 MHz, CDCl 3 ): 4.17 (d~bs, 2 H, CH 2 CCH), 3.78 (t, 2 H, β=och 2 ), 3.66, 3.64 (2 mc, 4+8 H, EG-CH 2 ), 3.4t (t, 2 H, α=ch 2 Br), 2.42 (t, CH); 3 J α,β = 6.5, 4 J propargyl ~ 2 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 71.06, 70.50, 70.48, 70.46, 70.38, 70.28, (7 EG-CH 2 ), (CH 2 CCH), (CH 2 Br). Diethyl 3,6-dioxa-8-nonynyl phosphonate (4a). Compound 3a (2.50 g, 12.0 mmol) was reacted according to general procedure C to give 4a (3.11 g, 98%) as a yellow oil. IR [KBr]: 2950, 2935, 2873 (CH), 2110 (C C), 1246 (P=O) cm H NMR (400 MHz, CDCl 3 ): 4.10 (d, 2H, CH 2 CCH), 3.99 (m c, 4 H, Et-CH 2 ), 3.63 (dt, 2 H, β=ch 2 O), 3.56 (A 2 B 2 -syst., 4 H, EG-CH 2 ), 2.36 (t, CH), 2.03 (dt, 2 H, α=ch 2 P), 1.21 (t, 6 H, CH 3 ); 3 J α,β = 7.5, 3 J Et = 7.0, 3 J P,α = 18.5, 4 J P,β = 11.0, 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 69.71, (3 EG-CH 2 ), (β=ch 2 O), 61.34, (2 Et-CH 2 ), (CH 2 CCH), (d, α=ch 2 P), 15.88, (2 Et-CH 3 ); 1 J C,P = 139 Hz. 31 P NMR (162 MHz, CDCl 3 ): Diethyl 3,6,9-trioxa-11-dodecynyl phosphonate (4b). Compound 3b (3.00 g, 11.3 mmol) was reacted according to general procedure C to give 4b (3.53 g, 97 %) as a yellow oil. IR [KBr]: 2984, 2911, 2873 (CH), 2112 (C C), 1244 (P=O) cm H NMR (400 MHz, CDCl 3 ): 4.18 (d, 2 H, CH 2 CCH), 4.07 (m c, 4 H, Et-CH 2 ), 3.70 (dt, 2 H, β=ch 2 O), (m, 10 H, EG-CH 2 ), 2.42 (t, CH), 2.11 (dt, 2 H, α=ch 2 P), 1.30 (t, 6 H, CH 3 ); 3 J α,β = 7.5, 3 J Et = 7.0, 3 J P,a = 18.5, 4 J P,b = 11.0, 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 70.42, 70.35, 70.10, (4 EG-CH 2 ), / 12 -
4 (β=ch 2 O), 61.62, (2 Et-CH 2 ), (CH 2 CCH), (d, α=ch 2 P), 16.39, (2 CH 3 ); 1 J C,P = 139 Hz. 31 P NMR (162 MHz, CDCl 3 ): Diethyl 3,6,9,12-tetraoxa-14-pentadecynyl phosphonate (4c). Compound 3c (4.70 g, 15.9 mmol) was reacted according to general procedure C to give 4c (5.50 g, 98 %) as a yellow oil. IR [KBr]: 2982, 2907, 2873, (CH), 2110 (C C), 1248 (P=O) cm H NMR (400 MHz, CDCl 3 ): 4.16 (d, 2 H, CH 2 CCH), 4.05 (m c, 4 H, 2 Et-CH 2 ), 3.68 (dt, 2 H, β=ch 2 O), 3.64, 3,58 (2 mc, 2 4 H, 4 EG-CH 2 ), 3.61 (~s, 4 H, 2 EG-CH 2 ), 2.41 (t, CH), 2.08 (dt, 2 H, α=ch 2 P), 1.28 (t, 6 H, CH 3 ); 3 J α,β = 7.5, 3 J Et = 7.0, 3 J P,α = 18.5, 4 J P,β = 11.0, 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): (C), (CH), 70.46, 70.44, 70.32, 70.26, 70.05, (6 EG-CH 2 ), (β=ch 2 O), 61.59, (2 Et-CH 3 ), (CH 2 CCH), (d, α=ch 2 P), 16.33, (2 CH 3 ); 1 J C,P = 139 Hz. 31 P NMR (162 MHz, CDCl 3 ): ,6-Dioxa-8-nonyne phosphonic acid (5a). Compound 4a (2.00 g, 7.56 mmol) was reacted according to general procedure D to give 5a (1.25 g, 80 %) as a yellow oil. IR [KBr]: 3419 (OH), 2935, 2881 (CH), 2118 (C C), 1244 (P=O) cm H NMR (400 MHz, CD 3 OD): 4.19 (d, 2 H, CH 2 CCH), 3.73 (dt, 2 H, β=ch 2 O), 3.68, 3.63 (A 2 B 2 -syst., 4 H, EG-CH 2 ), 2.88 (t, CH), 2.10 (dt, 2 H, α=ch 2 P); 3 J α,β = 7.5, 3 J P,α = 18.5, 4 J P,β = 11.5, 4 J propargyl ~ 2 Hz. 13 C NMR (100 MHz, CD 3 OD): (C), (CH), 70.95, (2 EG-CH 2 ), (β=ch 2 O), (CH 2 CCH), (d, α=ch 2 P); 1 J C,P = 136 Hz. 31 P NMR (162 MHz, CD 3 OD): ,6,9-Trioxa-11-dodecyne phosphonic acid (5b). Compound 4b (1.40 g, 4.34 mmol) was reacted according to general procedure D to give 5b (0.96 g, 88 %) as a yellow oil. IR [KBr]: 3422 (OH), 2925, 2883 (CH), 2117 (C C), 1246 (P=O) cm H NMR (400 MHz, CD 3 OD): 4.19 (d, 2 H, CH 2 CCH), 3.74 (dt, 2 H, β=ch 2 O), (m, 8 H, 4 EG-CH 2 ), 2.85 (t, CH), 2.09 (dt, 2 H, α=ch 2 P); 3 J α,β = 7.5, 3 J P,α = 18.5, 4 J P,β = 11.5, 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CD 3 OD): (C), (CH), 71.60, 71.49, 71.21, (4 EG-CH 2 ), (β=ch 2 O), (CH 2 CCH), (α=ch 2 P); 1 J C,P = 136 Hz. 31 P NMR (162 MHz, CD3OD): ,6,9,12-Tetraoxa-14-pentadecyne phosphonic acid (5c). Compound 4c (3.30 g, 9.36 mmol) was reacted according to general procedure D to give 5c (1.88 g, 68 %) as a yellow oil. IR [KBr]: 2913 (CH), 2117 (C C), 1246 (P=O) cm H NMR (400 MHz, CD 3 OD): 4.19 (d, 2 H, CH 2 CCH), 3.74 (dt, 2 H, β-ch 2 ), (m, 12 H, 6 EG-CH 2 ), 2.84 (t, CH), 2.08 (dt, 2 H, α=ch 2 P). 3 J α,β = 7.5, 3 J P,α = 18.5, 4 J P,β = 11.5, 4 J propargyl = 2.5 Hz. 13 C NMR (100 MHz, CD 3 OD): (C), (CH), 71.58, 71.53, 71.52, 71.39, 71.13, (6 EG-CH 2 ), (β=ch 2 O), (CH 2 CCH), (α=ch 2 P); 1 J C,P = 136 Hz. 31 P NMR (162 MHz, CD 3 OD): / 12 -
5 5-Tosyloxy-3-oxa-pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (9a). β-glucose pentaacetate (5.0 g, 13 mmol) and diethylene glycol monotosylate, 7a, (3.5 g, 14 mmol) were reacted with BF 3 OEt 2 (2.7 g, 19 mmol) according to general procedure E to give 9a (4.4 g, 60 %) as light yellow syrup. 1 H NMR (400 MHz, CDCl 3 ): 7.76, 7.32 (A 2 B 2 -Syst., 4 H, C 6 H 4 ), 5.20 (dd~t, H-3), 5.04 (dd~t, H-4), 4.93 (dd, H-2), 4.55 (d, H-1), 4.22 (dd, H-6A), 4.15 (t, 2 H, CH 2 OTs), 4.10 (dd, H-6B), 3.85 (dt, α-eg- A), (m, 4 H, H-5, α-eg-b, 2 EG), 2.41 (s, 3 H, CH 3 ), 2.04, 1.99, 1.98, 1.96 (4 s, 4 3 H, Ac); 3 J 1,2 = 8.0, 3 J 2,3 = 9.5, 3 J 3,4 = 9.5, 3 J 4,5 = 9.5, 3 J 5,6A = 4.5, 3 J 5,6B = 3.0, 2 J 6 = 12.5, 3 J α,β = 4.0, 3 J CH2OTs = 4.0, 2 J α = 11.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): , , , (CO), , (Ar-C), , (Ar-CH), (C-1), (C-3), (C-5), (C-2), 70.24, 68.85, (CH 2 O), (C-4), (C-6), (CH 3 ), 20.59, 20.50, (2) (Ac). 8-Tosyloxy-3,6-dioxa-octyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (9b). β-glucose pentaacetate (7.0 g, 18 mmol), triethylene glycol monotosylate, 7b, (5.7 g, 20 mmol) were reacted with BF 3 OEt 2 (3.8 g, 27 mmol) according to general procedure E to give 9b (6.8 g, 61 %) as light yellow syrup. 1 H NMR (400 MHz, CDCl 3 ): 7.79, 7.34 (A 2 B 2 -Syst. 4 H, C 6 H 4 ), 5.20 (dd~t, H-3), 5.07 (dd~t, H-4), 4.98 (dd, H-2), 4.56 (d, H-1), 4.25 (dd, H-6A), 4.14 (t, 2 H, CH 2 OTs), 4.12 (dd, H-6b), 3.93 (dt, α-eg-a), (m, 6 H, H-5, α-eg-b & 4 EG), 2.56 (s, 4 H, EG), 2.44 (s, 3 H, TsCH 3 ), 2.07, 2.02, 2.01, 1.99 (4 s, 4 3 H, Ac); 3 J 1,2 = 8.0, 3 J 2,3 = 9.5, 3 J 3,4 = 9.5, 3 J 4,5 = 9.5, 3 J 5,6A = 4.5, 3 J 5,6B = 3.0, 2 J 6 = 12.5, 3 J α,β = 4.0, 3 J CH2OTs = 5.0, 2 J α = 11.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): , , , (CO), , (Ar-C), , (Ar-CH), (C-1), (C-3), (C-5), (C-2), 70.75, 70.62, 70.29, 69.26, 69.13, (CH 2 O), (C-4), (C-6), (CH 3 ), 20.79, 20.71, 20.66, (Ac). 11-Tosyloxy-3,6,9-trioxa-undecyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (9c). β-glucose pentaacetate (10.0 g, 26 mmol), tetraethylene glycol monotosylate 7c (9.4 g, 28 mmol) were reacted with BF 3 OEt 2 (5.5 g, 38 mmol) according to general procedure E to give 9c (10.7 g, 63 %) as light yellow syrup. 1 H NMR (400 MHz, CDCl 3 ): 7.75, 7.31 (A 2 B 2 -Syst., 4 H, C 6 H 4 ), 5.16 (dd~t, H-3), 5.04 (dd~t, H-4), 4.93 (dd, H-2), 4.57 (d, H-1), 4.22 (dd, H-6A), 4.12 (t, 2 H, CH 2 OTs), 4.06 (dd, H-6B), 3.89 (dt, α-eg-a), (m, 10 H, H-5, α-eg-b, 8 EG), 2.40 (s, 3 H, CH 3 ), 2.03, 1.98, 1.97, 1.95 (4 s, 4 3 H, Ac); 3 J 1,2 = 8.0, 3 J 2,3 = 9.5, 3 J 3,4 = 9.5, 3 J 4,5 = 9.5, 3 J 5,6A = 4.5, 3 J 5,6B = 3.0, 2 J 6 = 12.5, 3 J α,β = 4.0, 3 J CH2OTs = 5.0, 2 J α = 11.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): , , , (CO), , (Ar-C), , (Ar-CH), (C-1), (C-3), (C-5), (C-2), 70.58, 70.51, 70.47, 70.34, 70.13, 69.11, 68.96, (CH 2 O), (C-4), (C-6), (CH 3 ), 20.35, 20.27, (2) (Ac). - 5 / 12 -
6 5-Azido-3-oxa-pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (10a). Compound 9a (4.0 g, 6.9 mmol) was reacted with NaN 3 (0.68 g, 10 mmol) according to general procedure F to provide 10a (2.9 g, 91 %) as give a pale yellow syrup. 1 H NMR (400 MHz, CDCl 3 ): 5.19 (dd~t, H-3), 5.06 (dd~t, H-4), 4.97 (dd, H-2), 4.60 (d, H-1), 4.23 (dd, H-6A), 4.12 (dd, H-6B), 3.93 (dt, α-eg-a), (m, 6 H, H-5, α-eg-b, 4 EG), 3.34 (m, 2H, CH 2 N 3 ), 2.06, 2.03, 2.00, 1.98 (4 s, 4 3 H, Ac); 3 J 1,2 = 8.0, 3 J 2,3 = 9.5, 3 J 3,4 = 9.5, 3 J 4,5 = 9.5, 3 J 5,6A = 5.0, 2 J 6 = 12.5, 3 J α,β = 4.5, 2 J α = 11.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): , , , (CO), (C-1), (C-3), (C-5), (C-2), 70.38, 70.12, (CH 2 O), (C-4), (C-6), (CH 2 N 3 ) 20.65, 20.58, 20.53, (Ac). 8-Azido-3,6-dioxa-octyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (10b). Compound 9b (6.0 g, 9.7 mmol) was reacted with NaN 3 (0.94 g, 15 mmol) according to general procedure F to provide 10b (4.5 g, 93 %) as a pale yellow syrup. 1 H NMR (400 MHz, CDCl 3 ): 5.17 (dd~t, H-3), 5.04 (dd~t, H-4), 4.95 (dd, H-2), 4.57 (d, H-1), 4.21 (dd, H-6A), 4.09 (dd, H-6b), 3.90 (dt, α-eg-a), (m, 10 H, H-5, α-eg-b, 8 EG), 3.35 (t, 2 H, CH 2 N 3 ), 2.03, 2.00, 1.97, 1.95 (4 s, 4 3 H, Ac); 3 J 1,2 = 8.0, 3 J 2,3 = 9.5, 3 J 3,4 = 9.5, 3 J 4,5 = 9.5, 3 J 5,6A = 5.0, 3 J 5,6B = 2.5, 2 J 6 = 12.5, 3 J α,β = 4.5, 3 J CH2N3 = 5.0, 2 J α = 11.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): , , , (C), (C-1), (C-3), (C-5), (C-2), 70.48, 70.45, 70.19, 69.80, (CH 2 O), (C-3), (C-6), (CH 2 N 3 ), 20.24, 20.17, (2) (Ac). 11-Azido-3,6,9-trioxa-undecyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (10c). Compound 9c (9.0 g, 14 mmol) was reacted with NaN 3 (1.3 g, 20 mmol) according to general procedure F to provide 10c (6.8 g, 91 %) as a pale yellow syrup. 1 H NMR (400 MHz, CDCl 3 ): 5.18 (dd~t, H-3), 5.05 (dd~t, H-4), 4.96 (dd, H-2), 4.59 (d, H-1), 4.23 (dd, H-6A), 4.11 (dd, H-6B), 3.93 (dt, α-eg-a), (m, 14 H, H-5, α-eg-b, 12 EG), 3.37 (t, 2H, CH 2 N 3 ), 2.06, 2.02, 2.00, 1.98 (4 s, 4 3 H, Ac); 3 J 1,2 = 8.0, 3 J 2,3 = 9.5, 3 J 3,4 = 9.5, 3 J 4,5 = 9.5, 3 J 5,6A = 5.0, 3 J 5,6B = 2.5, 2 J 6 = 12.5, 3 J α,β = 4.5, 3 J CH2N3 5.0, 2 J α = 11.5 Hz. 13 C NMR (100 MHz, CDCl 3 ): , , , (CO), (C-1), (C-3), (C-5), (C-2), (2), 70.62, 70.55, 70.24, 69.95, (CH 2 O), (C-4), (C-6), (CH 2 N 3 ), 20.65, 20.58, 20.53, (Ac). * C-NMR assignments for carbohydrate compounds 9 are based on HSQS correlation, while those for 10 base on analogy - 6 / 12 -
7 Selected NMR spectra - 7 / 12 -
8 - 8 / 12 -
9 - 9 / 12 -
10 SAXS measurement of in-situ surface modified LaPO 4 :Ce,Tb (6) SAXS measurements of powdered nanoparticles 6 and their dispersions in chloroform exhibited no major difference, indicating that the surface modification with dodecylamine, which enables the subsequent formation of a particle dispersion in chloroform, does not alter the particle core. The analysis of the scattering curves indicated an average particle radius of 3.1 nm at a polydispersity of ~55 %. Figure SX. SAXS curve for in-situ surface modified LaPO 4 Ce,Tb-nanoparicles 6 (left) and the correlated calculated radial distribution (right) - 10 / 12 -
11 Experimental details for the phenolic glucose assay Particle digestion. Receptor coupled nanoparticles 11 (10 mg) were digested in conc. HCl aq (500 µl) at gentle warming. The acid was subsequently neutralized with solid K 2 CO 3 before MeOH (1 ml) was added. After stirring the mixture for several minutes, solid contents were removed by filtration through a cotton layer and the solution was concentrated. The remaining material was dried in vacuum and then dissolved in water (8 ml) to provide the analytical sample. Assay for determination of glucose content. The analytical solution (200 µl) was treated with an aqueous solution of phenol (200 µl 0.5 mol/l) rapidly followed by the addition of conc. H 2 SO 4 (1000 µl). After 30 min the absorption was measured at 490 nm against a sample in which the analytical solution was replaced by pure water. The assay was calibrated with α-methyl glucoside and its accuracy for the model receptor was confirmed by its application on prepared samples of 10. Figure S1. Calibration curve for phenolic glucose assay and its application on nanoparticles 11; bold data points refer to methyl glucoside, while other data points reflect model receptor 10 The application of the phenolic acid on particles 11 led to an absorption of 0.1, referring to a glucose concentration of ~100 µmol L -1. This translates to model receptor content of ~8 µmol/10 mg. A replication practically confirmed the initial content. However, the experimental error was estimated to about 20 % based on ~15 % deviation of measurements from the average. Although this error is quite high, the value enables a reasonable accurate estimation of the receptor loading for practical purposes / 12 -
12 Estimation of model-receptor loading on nanoparticles Size of LaPO 4 :Ce.Tb particle core sphere model, diameter 5.5 nm * ; V core = 4 / 3 π r 3 = 87 nm 3 ρ(cepo 4 ) = 5.22 g cm -3 m core = V ρ = g M(LaPO 4 ) = 234 g mol -1 n core = m / M = (N A = mol -1 ) Model receptor-lanthanide ratio (x) Assay (10 mg 11): c Glc = 0.1 mmol L -1, V = 8 ml; n Glc = c V = 0.8 µmol TGA: m core (11) = 85 % m particle ; 10 mg mg LnPO 4 n LnPO4 = m / M = 36 µmol x Glc = n Glc : n LnPO4 = 1 : 45 Model receptor-particle ratio (y) y = n core X Glc = 26 Model receptor surface density TGA: m core (10) = 90 % m particle m shell = 10% / 90% m core = g assumption: shell density ρ shell ~ 1 g cm -1 V shell = r shell m shell = cm 3 = 50 nm 3 V particle = V core + V shell = 137 nm 3 r particle = 3.2 nm (spherical particle assumption) A particle = 4 π r 2 = 130 nm 2 surface area per model receptor ~5 nm 2 * reflecting volume average for elipsoids with (2 4.5 nm & 6.5 nm) and (4.5 nm & nm) axial distances reference surface is the surface of the particle shell that surrounds the inorganic core reference particle is in-situ modified but prior to receptor coupling, assuming that the particle size does not change upon receptor coupling; this assumes a receptor that is flexible attached to the surface but dissolved in the solvent - 12 / 12 -
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