Supplementary Material Investigation of SN2 [11C]cyanation for base-sensitive substrates: an improved radiosynthesis of L-[5-11C]-glutamine Tassilo Gleede†, ‡, Barbara Riehl†, ‡, Colleen Shea†, Lena Kersting†, ‡, Aylin Sibel Cankaya†, ‡, David Alexoff†, Michael Schueller†, Joanna S. Fowler†, Wenchao Qu*, † † Biological, Environmental and Climate Sciences Department, Brookhaven National Laboratory, Upton, NY 11973, USA ‡ Institut für Kernchemie, Johannes Gutenberg-Universität, D-55128, Mainz, Germany Email: wqu@bnl.gov Table of Contents Page S2 S2 S3 S4 Contents Scheme 1. Diagram of [ C]HCN production procedure Figure 1. Diagram of detailed Radiosynthesis process of L-[5-11C]-Glutamine Figure 2. Representative HPLC analysis result of synthesized radiotracer L-[511 C]-Glutamine Figure 3. Representative HPLC analysis result of Fmoc-[11C]Gln 11 S1 Scheme 1: Diagram of [11C]HCN production procedure. Figure 1: Diagram of detailed Radiosynthesis process of L-[5-11C]-Glutamine. S2 Quality analysis of L-[5-11C]-Glutamine Figure 2. Representative HPLC analysis result of synthesized radiotracer L-[5-11C]-Glutamine. Top: UV profile, L/D-Glutamine sample was co-injected with radiotracer sample for showing the retention time of both L- and D-glutamine. Bottom: Radio-HPLC profile, it shows that the synthesized radiotracer, L-[5-11C]-Glutamine, has high radiochemical and enantiomeric purities. S3 Figure 3. Representative HPLC analysis result of Fmoc-[11C]Gln. Top: UV profile of Fmocderivatized sample. Bottom: Radio-HPLC profile. S4