Effective cleavage of β-1,4-glycosidic bond by functional micelle with
L-histidine residue
Xiao-Hong Liao1, Ying Liu1,2, Xiao Peng1, Chun Mi1, Xiang-Guang Meng1,*
1 Key
Laboratory of Green Chemistry and Technology, Ministry of Education, College of
Chemistry, Sichuan University, Chengdu 610064, P. R. China
2 College
of Chemical Engineering, Guizhou Institute of Technology, Guiyang 550003, P. R. China
*Corresponding Author.Telephone: +86-28-85462979. Fax: +86-28-85412291. E-Mail:
[email protected].
1. Effect of pH on conversion of MCB in the absence of catalyst
Yield of reducing sugar /%
2.0
1.6
1.2
0.8
0.4
0.0
2
4
6
8
10
12
pH
Fig. S1 Yield of reducing sugar changes with pH for hydrolysis of MCB.
[MCB]0 = 2.0×10-3 mol·L-1, 90 °C, 10 h.
2. Varies of conversion of MCB with reaction time t at different temperatures.
70
60
Conversion of MCB /%
50
40
30
20
10
0
0
5
10
15
20
25
30
-1
t /h
Fig. S2 Plots of conversion of MCB vs. reaction time t at different temperatures. pH
4.0, [MCB]0 = 2.0×10-3 mol·L-1, [NDH] = 2.0×10-4 mol·L-1, 80 °C (■), 90 °C (●),
100 °C (▲), 105 °C (▼), 110 °C (◄).
3. Calculation of first order rate constant kobsd of conversion of MCB catalyzed
by NDH micelle
1.2
1.0
-ln(1-ct/co)
0.8
0.6
0.4
0.2
0.0
0
5
10
15
20
25
30
35
40
-3
10 t/s
Fig. S3 Plots of -ln(1-ct/c0) vs. reaction time t for conversion of MCB catalyzed by
NDH micelle at different temperatures. pH 4.0, [MCB]0 = 2.0×10-3 mol·L-1, [NDH] =
2.0×10-4 mol·L-1 , 80 °C (■), 90 °C (●), 100 °C (▲), 105 °C (▼), 110 °C (◄).
4. Calculation of first order rate constant kobsd of generation of monosaccharide
catalyzed by NDH micelle
0.8
0.7
0.6
-ln(1-ct/co)
0.5
0.4
0.3
0.2
0.1
0.0
-0.1
0
5
10
15
20
25
30
-3
10 t /s
Fig. S4 Plots of -ln(1-ct/c0) vs. reaction time t for generation of monosaccharide
catalyzed by NDH micelle at different temperatures. pH 4.0, [MCB]0 =
2.0×10-3mol·L-1, [NDH] = 2.0×10-4 mol·L-1 , 80 °C (■), 90 °C (●), 100 °C (▲),
105 °C (▼), 110 °C (◄).
5. NMR Data of Methyl-β-D-Cellobioside (MCB)
1
H NMR (400 MHz, DMSO-d6): δ 5.17 (d, 1H, OH-2'), 5.10 (d, 1H, OH-2), 4.95 (d,
1H,OH-3'), 4.92 (d, 1H, OH-4'), 4.64 (br, 1H, OH-3), 4.54 (m, 2H, OH-6/-6'), 4.25 (d,
1H, H-1'), 4.09 (d, 1H, H-1), 3.76–3.67 (2H, H-6/-6'),3.41- 3.61 (2H, H-5/-5'), 3.38 (s,
3H, OMe), 3.32–3.22 (3H, H-3/-4/-5), 3.21–3.11 (2H, H-5'/-3'), 3.04 (m, 1H, H-4'),
3.03–2.96 (2H, H-2/-2');
13
C NMR (100 MHz, DMSO-d6): δ 103.5 (C-1), 103.0 (C-1'), 80.3 (C-4), 76.7
(C-5'), 76.4 (C-3'), 74.9 (C-3), 74.7 (C-5), 73.2 (C-2'), 73.0 (C-2), 70.0 (C-4'), 61.0
(C-6'), 60.4 (C-6), 56.0 (OMe).
Scheme S1 The route of synthesis of Methyl-β-D-Cellobioside