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S1 Nanometer arrays of functional light harvesting antenna complexes bynanoimprint lithography and host-guest interactionsMaryana Escalante,aYiping Zhao,b,cManon J. W. Ludden,bRolf Vermeij,bJohn D. Olsen,d Erwin Berenschot,cC. Neil Hunter,dJurriaan Huskens,b*Vinod Subramaniama*and Cees Ottoa*aBiophysical Engineering Group, bMolecular Nanofabrication Group. cTransducerScience and Technology Group. MESA+ Institute for Nanotechnology. University ofTwente P.O. Box 217, 7500 AE Enschede, The Netherlands. dDepartment of MolecularBiology and Biotechnology, University of Sheffield, Sheffield S10 2TN,UK.*E-mail: c.otto@utwente.nl, v.subramaniam@utwente.nl, j.huskens@utwente.nlSupporting informationMaterialsAll Chemicals were used as received: N-[3-(trimethoxysilyl)propyl]-ethylenediamine](Aldrich), 1H,1H,2H,2H-perfluorodecyltrichlorosilane(ABCR), 2-[Methoxy(polyethyleneoxy)propyl]trimethoxysilane (ABCR), PMMA (molecular weight350 kD, Aldrich), 2-[Methoxy(polyethyleneoxy)propyl]trimethoxysilane (ABCR), 1,4-
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S2 phenylenediisothiocyanate(Acros).CD-heptamineand hexa(ethyleneglycol)mono(adamantyl ether) were synthesized as reported before.1, 2Scheme 1. SynthesisIodoacetyl-tri(ethylene glycol))mono(adamantyl ether) was prepared by dissolvingcompound 13(163 mg, 0.50 mmol) and iodoacetic anhydride (200 mg, 0.56 mmol) inDMF. To this mixture diisopropylethylamine (129 mg, 1 mmol) was added. The reactionwas performed in the dark in an icebath at 0 °C for 1 hour. Subsequently, THF wasremoved by rotary evaporation under vacuum, giving a brown colored oil as the product(yield 172 mg. 64 %).1H NMR (300 MHz, CDCl3): : 7.75-3.50 (m, 16H, OCH2CH2O + OCH2CH2NH), 2,85(m, 4H, CH2NH + CH2I), 2.15 (m, 3H, CH2CHCH2Ad), 1.76-1.75 (m, 16H, CHCH2CAd), 1.64-1.58 (m, 6H, CHCH2CHAd); MS (FAB-MS): m/z calculated for[M+H+] 596.4, found 597.5.Protein purificationThe LH2 complex was solubilized from membranes from photosynthetically grownRhodobacter sphaeroides using 4% N,N-Dimethyldodecylamine-N-oxide (LDAO), andpurified on DEAE (Sigma) and Resource Q (GE Healthcare) columns, then sizefractionated on a Superdex 200 gel filtration column (GE Healthcare). The mutagenesisprotocol has been described before.4