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1 Supporting Information Yi et al /pnas Fig. S1. Disruption of GDP-fucose de novo pathway and complementation with salvage pathway. Lane 1. LPS from wild-type E. coli O86; lane 2. Disruption of de novo pathway (gmd-fcl); lane 3. complementation of de novo pathway with ptrc99a-f; lane 4. complemented with salvage pathway (pet15b-fkp), grown in LB without sugar supplement; lane 5. complemented with salvage pathway (pet15b-fkp), grown in LB supplemented with 0.1% glucose; lane 6. complemented with salvage pathway (pet15b-fkp), grown in LB supplemented with 0.1% fucose. Yi et al. 1of24
2 Fkp Fig. S2. Expression and purification of Fkp. Lane 1. Protein Standard; lane 2. Proteins in whole cell of Fkp-expressing BL21(DE3); lane 3. Soluble protein fractions; lane 4. Inclusion body; lane 5. Flow-through from Ni-affinity purification; lane 6. Eluted Fkp from Ni-affinity purification. Yi et al. 2of24
3 Fig. S3. In vitro Fkp reaction with fucose as substrate. Lane 1. ATP; lane 2. GTP; lane 3. L-fucose; lane 4. GDP-fucose; lane 5. ADP; lane 6. starting point of GDP-fucose synthesis reaction; lane 7. GDP-fucose synthesis reaction after 30 min. Yi et al. 3of24
4 A. Fucose, compound 1, product MS (ESI): UV - 254nm 0.1mM FourMix-254nm-pH10buf-01-5/5/2008 9:08:49 PM Area Percent Area ADP GTP GDP-Fuc ATP [1] Minutes B. compound 2, product MS (ESI): UV - 254nm D-Ara(2mM)_2hr_1.2ugE_9/8/2008 4:20:05 PM Area Percent Area Minutes Fig. S4. Capillary electrophoresis analysis of Fkp reactions with various fucose analogs. Yi et al. 4of24
5 C. compound 3, product MS (ESI): UV - 254nm L-Gal(2mM)_2hr_1.2ugE_9/8/2008 3:20:05 PM Area Percent Area Minutes D. compound 4, product MS (ESI): UV - 254nm Fuc-N3(2mM)_2hr_1.2ugE_9/8/2008 3:53:07 PM Area Percent Area Fig. S4. Yi et al. 5of24
6 E. compound 5, product MS (ESI): UV - 254nm Gal-NH2(2mM)_2hr_1.2ugE_9/8/2008 7:25:24 PM Area Percent Area F. compound 6, product MS (ESI): UV - 254nm R=CH2CH3_2hr_3.72ugE_9/15/ :40:27 AM Area Percent Area Minutes Fig. S4. Yi et al. 6of24
7 G. compound 7, product MS (ESI): UV - 254nm R=CH()CH3_2hr_3.72ugE_9/15/ :09:11 AM Area Percent Area Minutes H. compound 8, product MS (ESI): UV - 254nm Keto(2mM)_2hr_1.2ugE_9/8/2008 5:27:32 PM Area Percent Area Minutes Fig. S4. Yi et al. 7of24
8 I. compound 9, product MS (ESI): UV - 254nm Aldehyde(2mM)_2hr_1.2ugE_9/8/2008 6:27:44 PM Area Percent Area Minutes J. compound 10, product MS (ESI): UV - 254nm Alkyne_2hr_3.72ugE_9/15/ :34:21 AM Area Percent Area Minutes Fig. S4. Yi et al. 8of24
9 A. MS spectrum of LPS (compound 1). +Q1: to min from Sample 1 (Fuc 1; Q1+ DP 400) of IJLXL080422B03.wiff (Turbo Spray), subtracted (1.370 to min),... Max. 1.1e6 cps. 100% % 90% % 80% % 70% 65% 60% 55% 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% Fig. S5. Rel. Int. (% ) MS spectra of intact LPSs. Yi et al. 9of24
10 B. MS spectrum of LPS (3) +Q1: to min from Sample 3 (L-Gal 1; Q1+ DP 400) of IJLXL080422B01.wiff (Turbo Spray), subtracted (2.306 to min),... Max. 3.5e5 cps. 100% % 90% 85% 80% 75% % 65% 60% 55% % 45% 40% % 30% 25% % 15% 10% 5% Rel. Int. (%) Fig. S5. Yi et al of 24
11 C. MS spectrum of LPS (2) +Q1: to min from Sample 1 (DAra-1; Q1+ DP 400) of IJLXL080422B07.wiff (Turbo Spray), subtracted (1.504 to min),... Max. 4.2e5 cps. 100% % % 85% 80% 75% 70% % 60% 55% 50% % 40% 35% 30% 25% 20% 15% 10% 5% Rel. Int. (%) Fig. S5. Yi et al of 24
12 D. MS spectrum of LPS (4) +Q1: to min from Sample 1 (Fuc-N3 1; Q1+ DP 400) of IJLXL080422B06.wiff (Turbo Spray), Smoothed Max. 1.1e5 cps. 100% % 90% 85% % 75% 70% % % 55% % % 40% % 30% 25% 20% 15% 10% 5% Rel. Int. (%) Fig. S5. Yi et al of 24
13 E. MS spectrum of LPS (5) +Q1: to min from Sample 1 (U. Ohio, CPS-GalN, DP=400V) of IJLJL080429A01.wiff (Turbo Spray), Smoothed Max. 1.3e6 cps. 1.30e e6 1.10e6 1.00e6 9.00e e5 7.00e5 6.00e5 5.00e5 4.00e e5 2.00e5 1.00e Fig. S5. In te n s ity, c p s Yi et al of 24
14 F. MS spectrum of LPS (6) Fig. S5. Yi et al of 24
15 G. MS spectrum of LPS (7) Fig. S5. Yi et al of 24
16 H. MS spectrum of LPS (8) +Q1: to min from Sample 1 (Wang Keto; Q1+ DP 400) of IJLXL080825A08.wiff (Turbo Spray), subtracted (2.172 to Max. 9.8e5 cps. 9.8e5 9.5e e5 8.5e5 8.0e5 7.5e5 7.0e e5 6.0e5 5.5e5 5.0e e e e5 3.0e e5 2.0e5 1.5e5 1.0e5 5.0e Intensity, cps Fig. S5. Yi et al of 24
17 I. MS spectrum of LPS (9) +Q1: to min from Sample 1 (Wang Aldehyde; Q1+ DP 400) of IJLXL080825A09.wiff (Turbo Spray), subtracted (1.504 to 2... Max. 3.2e5 cps. 3.2e e e5 2.6e5 2.4e5 2.2e e5 1.8e5 1.6e5 1.4e5 1.2e5 1.0e5 8.0e4 6.0e4 4.0e4 2.0e Fig. S5. Intensity, cps Yi et al of 24
18 J. MS spectrum of LPS (10) +Q1: to min from Sample 1 (Wang Alkyne; Q1+ DP 400) of IJLXL080825A10.wiff (Turbo Spray), subtracted (2.339 to Max. 5.9e5 cps. 5.9e e5 5.0e5 4.5e e5 3.5e5 3.0e5 2.5e5 2.0e e5 1.0e5 5.0e Fig. S5. Intensity, cps Yi et al of 24
19 O HO 1 O HO 2 HO N O 3 O H 2 N HO HO 3 4 O HO 5 HO O O O O O O O H HO HO HO HO HO Fig. S6. Analysis of LPSs fed with different fucose analogs. Chemical structures of compounds are shown. Yi et al of 24
20 A. compound Int en sit y, cp Fig. S7. Precursor-treated MS spectra. Yi et al of 24
21 B. compound Fig. S7. Yi et al of 24
22 C. compound Fig. S7. Yi et al of 24
23 D. compound 10 +Prec (204.20): to min from Sample 1 (Wang Alkyne; DP 400, pre@204) of IJLXL080825A11.wiff (Turbo Max. Spray), Int en sit y, cp m/z, Fig. S7. Yi et al of 24
24 fucn fuc + Cu TCEP Ligand Fig. S8. Control experiments for in vitro polysaccharide labeling. Other Supporting Information Files SI Appendix Yi et al of 24
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