Supplementary Material
Table S1. ____________________________________________________________
EA-RESP charges and standard deviations for methyl xylo-, fuco-,
N
-Acetyl-gluco-,
and
N
-Acetyl-galactopyranoside
Atom α-D-xylo-pyranoside
β-D-xylo-pyranoside
α-L-fuco-pyranoside
N-Acetyl α-D-glucopyranoside
N-Acetyl β-D-glucopyranoside
N-Acetyl α-D-galactopyranoside
C1 0.15 (0.08) 0.17 (0.07) 0.11 (0.07) 0.05 (0.04) 0.07 (0.05) 0.10 (0.08) C2 0.14 (0.05) 0.08 (0.05) 0.17 (0.05) 0.02 (0.03) 0.03 (0.03) 0.04 (0.04) C3 0.22 (0.07) 0.24 (0.08) 0.23 (0.08) 0.14 (0.06) 0.12 (0.06) 0.16 (0.06) C4 0.19 (0.05) 0.22 (0.06) 0.07 (0.06) 0.18 (0.08) 0.21 (0.08) 0.12 (0.06) C5 0.08 (0.04) 0.05 (0.03) 0.20 (0.06) 0.09 (0.07) 0.05 (0.05) 0.07 (0.06)
C6 --- --- -0.07 (0.02) 0.21 (0.07) 0.24 (0.07) 0.25 (0.08)
C-OMe 0.03 (0.01) 0.06 (0.01) 0.01 (0.01) 0.02 (0.02) 0.04 (0.02) 0.01 (0.03) O1 -0.32 (0.02) -0.34 (0.02) -0.31 (0.02) -0.32 (0.03) -0.33 (0.03) -0.31 (0.03)
O2 -0.66 (0.02) -0.64 (0.02) -0.65 (0.02) --- ---
---O3 -0.68 (0.02) -0.67 (0.02) -0.66 (0.02) -0.65 (0.03) -0.64 (0.03) -0.64 (0.02) O4 -0.68 (0.02) -0.69 (0.02) -0.64 (0.03) -0.67 (0.02) -0.69 (0.02) -0.63 (0.02) O5 -0.46 (0.03) -0.38 (0.03) -0.41 (0.03) -0.36 (0.03) -0.28 (0.05) -0.37 (0.03)
O6 --- --- --- -0.67 (0.02) -0.68 (0.02) -0.68 (0.03)
N2 --- --- --- -0.52 (0.07) -0.52 (0.07) -0.58 (0.08)
CN2 --- --- --- 0.72 (0.06) 0.71 (0.05) 0.74 (0.06)
HN2 --- --- --- 0.29 (0.03) 0.30 (0.03) 0.31 (0.03)
O=CN2 --- --- --- -0.62 (0.02) -0.61 (0.02) -0.62 (0.01)
C-Ac --- --- --- -0.24 (0.06) -0.22 (0.07) -0.23 (0.04)
<HC-Ac> --- --- --- 0.07 (0.02) 0.06 (0.03) 0.07 (0.01)
H1 0.14 (0.02) 0.11 (0.01) 0.13 (0.02) 0.16 (0.02) 0.13 (0.02) 0.15 (0.03) H2 0.09 (0.03) 0.10 (0.02) 0.10 (0.03) 0.15 (0.02) 0.17 (0.02) 0.17 (0.02) H3 0.07 (0.03) 0.06 (0.02) 0.04 (0.03) 0.08 (0.02) 0.08 (0.03) 0.05 (0.03) H4 0.07 (0.03) 0.05 (0.03) 0.08 (0.02) 0.10 (0.03) 0.08 (0.03) 0.09 (0.02) H5A 0.07 (0.02) 0.05 (0.01) 0.03 (0.02) 0.09 (0.02) 0.05 (0.02) 0.07 (0.02)
H5E 0.09 (0.01) 0.10 (0.01) --- --- ---
---<H6> --- --- 0.03 (0.01) --- ---
---H61 --- --- --- 0.04 (0.04) 0.03 (0.03) 0.04 (0.03)
H62 --- --- --- 0.04 (0.03) 0.03 (0.03) 0.03 (0.04)
<H-OMe> 0.06 (0.01) 0.06 (0.01) 0.06 (0.01) 0.06 (0.01) 0.06 (0.01) 0.06 (0.01)
HO2 0.43 (0.02) 0.43 (0.02) 0.42 (0.02) --- ---
---HO3 0.43 (0.02) 0.43 (0.02) 0.43 (0.02) 0.43 (0.02) 0.42 (0.02) 0.42 (0.02) HO4 0.43 (0.02) 0.43 (0.02) 0.43 (0.02) 0.43 (0.02) 0.44 (0.02) 0.44 (0.02)
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for
Methyl -D-Galactopyranoside (3
1)Atom X Y Z
C -1.172573 -0.423511 -0.854153 O -1.172616 -0.423679 0.529764 C 0.089220 -0.423583 1.168152 C 0.946871 0.755018 0.720481 C 1.032900 0.764773 -0.800442 C -0.363313 0.742668 -1.407260 H -2.212039 -0.337489 -1.147990 H -0.868720 1.659446 -1.140635 H 0.621695 -1.336976 0.922100 O -0.626604 -1.584673 -1.390866 C -1.363701 -2.757621 -1.166473 H -0.842885 -3.560997 -1.667331 H -1.436552 -2.979057 -0.109156 H -2.364506 -2.668455 -1.579724 C -0.200620 -0.422148 2.657337 H -0.887094 -1.234687 2.877463 H -0.672906 0.512932 2.928869 O 1.021587 -0.601557 3.324473 O -0.299536 0.708817 -2.807886 H -0.096576 -0.180949 -3.071447 H 1.579909 -0.114974 -1.131531 O 1.717130 1.928924 -1.183445 H 1.592709 2.056580 -2.116085 H 1.940676 0.634235 1.139004 O 0.368033 1.945826 1.178085 H 0.829806 2.665986 0.766421 H 0.939817 -0.318431 4.223195
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for
Methyl -D-Galactopyranoside (3
2)Atom X Y Z
Table S4. ______________________________________
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for Methyl -D-Galactopyranoside (33)Atom X Y Z
C -1.013792 -0.349885 -0.827629 O -1.013695 -0.349884 0.557477 C 0.252484 -0.349990 1.197283 C 1.099395 0.836905 0.756062 C 1.175813 0.867854 -0.765776 C -0.222113 0.832941 -1.370077 H -2.054287 -0.279517 -1.122509 H -0.740108 1.739820 -1.093185 H 0.779311 -1.261514 0.933296 O -0.447026 -1.498312 -1.365790 C -1.139710 -2.692877 -1.109099 H -0.625932 -3.478231 -1.644220 H -1.145290 -2.922348 -0.051112 H -2.163692 -2.628174 -1.466134 C -0.040021 -0.376736 2.686879 H -0.576583 0.521429 2.966830 H 0.889424 -0.406385 3.240851 O -0.757143 -1.528719 3.031870 O -0.157048 0.815239 -2.770238 H 0.055386 -0.068923 -3.045260 H 1.733280 0.000055 -1.109988 O 1.842533 2.046027 -1.133499 H 1.714547 2.186696 -2.063902 H 2.104047 0.712645 1.156738 O 0.529570 2.018693 1.241244 H 0.971260 2.747137 0.821450 H -1.591227 -1.496317 2.582761
Table S5. ______________________________________
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for Methyl -D-Galactopyranoside (31)Atom X Y Z
C -0.842611 -0.648501 -0.870998 O -0.898267 -0.586177 0.518114 C 0.357024 -0.615770 1.154114 C 1.235340 0.553698 0.711633 C 1.307976 0.588019 -0.811798 C -0.087491 0.553532 -1.408388 H -0.344555 -1.572988 -1.173500 H -0.629787 1.443017 -1.108133 H 0.875394 -1.538769 0.895202 O -2.113084 -0.608663 -1.390257 C -2.926026 -1.714229 -1.096390 H -3.850574 -1.576615 -1.638305 H -2.455812 -2.638075 -1.423527 H -3.133661 -1.774604 -0.036473 C 0.081945 -0.626938 2.645940 H -0.611276 -1.434235 2.863145 H -0.377584 0.310801 2.929355 O 1.307700 -0.826167 3.300426 O 0.054656 0.496767 -2.802252 H -0.808830 0.494912 -3.195160 H 1.853971 -0.285672 -1.163734 O 1.988098 1.756891 -1.180897 H 1.905196 1.869041 -2.119949 H 2.232349 0.406367 1.113782 O 0.686489 1.746021 1.196987 H 1.141805 2.465561 0.777156 H 1.241691 -0.536988 4.198488
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for Methyl -D-Galactopyranoside (32)
Atom X Y Z
C -0.688207 -0.747025 -0.856269 O -0.746083 -0.686762 0.531891 C 0.500280 -0.715817 1.176954 C 1.392531 0.443612 0.725446 C 1.455683 0.497009 -0.797196 C 0.058642 0.462601 -1.388150 H -0.183983 -1.667994 -1.161507 H -0.488299 1.346138 -1.077643 H 1.025119 -1.635798 0.909992 O -1.956398 -0.711136 -1.378152 C -2.780198 -1.802321 -1.055783 H -3.700180 -1.672492 -1.606997 H -2.315048 -2.738345 -1.354538 H -2.992294 -1.828563 0.004107 C 0.255191 -0.760125 2.682944 H 1.226120 -0.770885 3.179214 H -0.242186 -1.692376 2.916978 O -0.555925 0.257519 3.168507 O 0.200038 0.421458 -2.781527 H -0.663891 0.405724 -3.173697 H 2.003125 -0.370703 -1.160544 O 2.132118 1.672285 -1.150335 H 2.038904 1.804894 -2.086000 H 2.395568 0.277530 1.112251 O 0.885475 1.649702 1.231747 H 1.326074 2.366331 0.789890 H -0.266362 1.084414 2.803777
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for Methyl -D-Galactopyranoside (33)
Atom X Y Z
Table S8. ______________________________________
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for
Methyl -D-Glucopyranoside (1
1)Atom X Y Z
H 0.076017 -2.729745 -2.858422 C 0.075063 -2.730077 -1.778245 H 1.095104 -2.730808 -1.416219 H -0.430507 -3.622403 -1.420578 O -0.609089 -1.573673 -1.367288 C -0.757097 -1.420915 0.003459 H -1.161428 -2.328545 0.435716 C -1.714918 -0.251845 0.217673 H -2.000252 -0.233379 1.261896 O -2.896160 -0.407676 -0.516563 H -2.662751 -0.700175 -1.389836 C -1.032610 1.066816 -0.118491 H -0.826905 1.105068 -1.185727 O -1.825581 2.161324 0.256371 H -2.685984 2.062605 -0.132269 C 0.279852 1.175824 0.632692 H 0.066745 1.172029 1.699978 O 0.969874 2.347143 0.286648 H 0.377666 3.083628 0.380463 C 1.158406 -0.028345 0.308327 H 1.394042 -0.026469 -0.749976 O 0.450146 -1.204825 0.652862 C 2.464908 -0.057139 1.093445 H 2.255614 0.077581 2.153140 H 2.916329 -1.032124 0.970293 O 3.382719 0.882673 0.624409 H 2.969416 1.737099 0.606873
Table S9. ______________________________________
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for Methyl -D-Glucopyranoside (12)Atom X Y Z
H -2.416798 -2.648519 -1.777650 C -1.870240 -2.546265 -0.851517 H -0.905164 -3.027605 -0.947143 H -2.428510 -3.024797 -0.051960 O -1.730116 -1.170846 -0.605729 C -1.083663 -0.836334 0.575007 H -1.520493 -1.382706 1.402850 C -1.258074 0.665725 0.770440 H -0.920466 0.920911 1.766943 O -2.605189 1.041222 0.697560 H -2.990615 0.607911 -0.054870 C -0.418756 1.434067 -0.239189 H -0.805580 1.250297 -1.239158 O -0.433326 2.809691 0.033888 H -1.335349 3.098159 0.096524 C 1.026952 0.973490 -0.191160 H 1.443751 1.225372 0.779201 O 1.774074 1.563412 -1.216413 H 1.698982 2.505827 -1.135369 C 1.096655 -0.536660 -0.384130 H 0.768607 -0.775163 -1.390637 O 0.259969 -1.184860 0.564447 C 2.486960 -1.108892 -0.164895 H 2.472466 -2.165947 -0.421183 H 3.188688 -0.608405 -0.815196 O 2.930473 -0.922894 1.147491 H 2.304393 -1.331927 1.730356
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for Methyl -D-Glucopyranoside (13)
Atom X Y Z
H 0.258237 3.360331 1.830088 C 0.483157 2.933799 0.863583 H 1.500533 2.564159 0.861426 H 0.378573 3.700399 0.101026 O -0.435640 1.892270 0.650436 C -0.366177 1.275213 -0.588999 H -0.419617 2.018220 -1.376351 C -1.546165 0.312263 -0.675224 H -1.621668 -0.041363 -1.695687 O -2.757716 0.949892 -0.382835 H -2.627005 1.491569 0.386656 C -1.326264 -0.886069 0.238022 H -1.345042 -0.554614 1.273761 O -2.307310 -1.866866 0.031517 H -3.162920 -1.465256 0.118701 C 0.023454 -1.526341 -0.034272 H 0.019950 -1.914077 -1.051855 O 0.292985 -2.550286 0.877917 H -0.444746 -3.147588 0.882469 C 1.116513 -0.474394 0.093279 H 1.148216 -0.110322 1.113531 O 0.831800 0.602781 -0.789169 C 2.495463 -0.976347 -0.292339 H 2.792553 -1.768813 0.377833 H 2.464753 -1.375910 -1.303902 O 3.449149 0.040987 -0.184862 H 3.192168 0.744303 -0.766022
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for
Methyl -D-Glucopyranoside (1
1)Atom X Y Z
Table S12. _____________________________________ Optimized (HF/6-31G*//6-31G*) coordinates (Å) for Methyl -D-Glucopyranoside (12)
Atom X Y Z
H 1.547822 -1.541311 -3.872131 C 1.549101 -1.540539 -2.791891 H 2.575993 -1.539595 -2.436518 H 1.046470 -2.427670 -2.429629 O 0.878750 -0.376013 -2.384243 C 0.850979 -0.145897 -1.031897 H 1.860277 -0.197045 -0.619897 C 0.263438 1.236052 -0.805763 H -0.721781 1.257471 -1.263368 O 1.083472 2.238249 -1.337730 H 1.149682 2.113132 -2.275766 C 0.137093 1.489336 0.684084 H 1.136155 1.507745 1.116736 O -0.519784 2.696595 0.954360 H -0.050437 3.400922 0.525127 C -0.657215 0.376965 1.349533 H -1.680705 0.415716 0.990927 O -0.615724 0.503549 2.741949 H -0.954709 1.358844 2.974152 C -0.061928 -0.983402 0.994263 H 0.921998 -1.063692 1.454115 O 0.050189 -1.105033 -0.410253 C -0.918670 -2.152257 1.451695 H -0.378558 -3.075528 1.254974 H -1.095575 -2.077420 2.514223 O -2.165775 -2.161754 0.821299 H -2.022444 -2.177869 -0.116138
Table S13. _____________________________________
Optimized (HF/6-31G*//6-31G*) coordinates (Å) for
Methyl -D-Glucopyranoside (1
3)Atom X Y Z
H 1.342227 -1.481464 -3.911384 C 1.343451 -1.480690 -2.831172 H 2.369916 -1.479938 -2.475124 H 0.841439 -2.369532 -2.471677 O 0.671154 -0.318015 -2.423270 C 0.672344 -0.066362 -1.074481 H 1.691095 -0.101147 -0.685248 C 0.075911 1.314822 -0.861398 H -0.917608 1.316998 -1.301053 O 0.874177 2.316525 -1.425824 H 0.927269 2.173565 -2.362191 C -0.027863 1.597383 0.625493 H 0.977601 1.643915 1.040180 O -0.704883 2.796088 0.884210 H -0.256652 3.502119 0.435477 C -0.787152 0.483325 1.328009 H -1.814330 0.491842 0.968296 O -0.751521 0.648596 2.715023 H -1.052069 1.525558 2.919157 C -0.157347 -0.864899 0.991887 H 0.851062 -0.902010 1.398287 O -0.107920 -1.016738 -0.414014 C -0.943476 -2.047013 1.528366 H -0.983199 -1.995957 2.605946 H -1.960619 -2.002478 1.144590 O -0.332392 -3.257192 1.189982 H -0.260249 -3.294979 0.245661
