Page S1 Direct chemoselective synthesis of glyconanoparticles from unprotected reducing glycans and glycopeptide aldehydes Mikkel B. Thygesen, Kasper K. Sørensen, Emiliano Cló and Knud J. Jensen* IGM -Bioorganic Chemistry, Centre for Carbohydrate Recognition and Signalling, Faculty of Life Sciences, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Frederiksberg C, Denmark. Fax: +45 3533 2398; Tel: +45 3533 2430; E-mail: kjj@life.ku.dk Supplementary Information Table of contents: I) Experimental procedures ........................................................................................................ S2 II) UV-Vis spectra of self-assembly of Trim-protected OEG linker 2 onto AuNPs.................. S7 III) Calibration curve for 6-carboxy-2,3-dihydrophthalazine-1,4-dione (5) .............................. S7 IV) Quantification of Trim cleavage from AuNPs 3 ................................................................. S8 V) UV-Vis spectra of Fmoc cleavage from AuNPs 6................................................................ S9 VI) Dynamic light scattering measurements on AuNPs 3, 4, and 6 ........................................ S10 VII) Comparison of UV-Vis spectra of citrate-AuNPs and AuNPs 3, 4, and 9(I)................... S10 VIII) Transmission electron microscopy analyses of citrate AuNPs, and AuNPs 4 and 6 ...... S11 IX) UV-Vis spectra and kinetics of lectin-induced nanoparticle aggregation ......................... S12 X) Detection limit of Con A-induced nanoparticle aggregation of 9(I) .................................. S13 IX) NMR spectra of compounds 2-Tr, 2, and 5 ...................................................................... S14 References ................................................................................................................................ S17 Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2009