Supporting Information Using Boronolectin in MALDI-MS Imaging for the Histological Analysis of Cancer Tissue Expressing the Sialyl Lewis X Antigen Chaofeng Dai, † Lisa H. Cazares, ‡ Lifang Wang, † Yong Chu, †Ŧ Siming L. Wang, † Dean A. Troyer, ‡ O. John Semmes, ‡ Richard R. Drake, ‡ * and Binghe Wang † * † Department of Chemistry, and Center for University, P.O. Box 4098, Atlanta, GA, 30302-4098, USA; ‡ Department of Microbiology and Molecular Cell Biology and The Leroy T. Canoles Jr. Cancer Research Center, Eastern Virginia Medical School, Norfolk, Virginia, 23507, USA; Ŧ Department of Medicinal Chemistry, School of Pharmacy, Fudan University. No.826, Zhangheng Rd, Shanghai, 201203, China. Corresponding Author: wang@gsu.edu; drakerr@evms.edu General Information S1 Synthetic procedure S2 – S8 Tissue preparation and MALDI-IMS S8 Immunostaining for Sialyl Lewis X S9 Borono-lectin trityl is blocked by carbohydrate S10 Spectra of prepared compounds S11 – S29 General Information Solvents and reagents were purchased from VWR, Acros, or Aldrich and used without purification unless specified otherwise. When necessary, solid reagents were dried under high vacuum. Reactions with compounds sensitive to air or moisture were performed under argon. Solvent mixtures are indicated as volume/volume ratios. Thin layer chromatography (TLC) was run on Sorbtech W/UV254 plates (0.25 mm thick), and visualized under UV-light or by a Ce-Mo staining solution (phosphomolybdate, 25 g; Ce(SO 4 ) 2 .4H 2 O, 10 g; H 2 SO4, 60 mL, conc.; H 2 O, 940 mL) with heating. Flash chromatography was performed using Fluka silica gel 60 (mesh size 0.040-0.063 mm) using a weight ratio of ca. 30:1 for silica gel over crude compound. 1 H, 13 C NMR spectra were recorded on a Bruker 400 MHz NMR spectrometer in deuterated chloroform (CDCl 3 ), methanol-d 4 (CD 3 OD), or DMSO-d 6 with either tetramethylsilane (TMS) (0.00 ppm) or the NMR solvent as the internal reference. S1 Electronic Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2011