Supporting information A practical solution-phase synthesis of an antagonistic peptide of TNF- based on hydrophobic tag strategy Gegen Tana, 1 Shingo Kitada, 1 Shuji Fujita, 2 Yohei Okada, 1 Shokaku Kim, 1 Kazuhiro Chiba 1* 1 Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan 2 JITSUBO Co. Ltd., 2-24-16 Naka-cho, Koganei, Tokyo 184-0012, Japan Phone: +81-42-367-5667, Fax: +81-42-360-7167 chiba@cc.tuat.ac.jp Table of contents: 1. General information 2. Additional schemes and figures 3. Experimental information 3.1. Investigation of hydrophobic tag HO-TAGa (1) 3.1.1. Preparation of N-Boc-Leu-O-TAGa (4) 3.1.2. Acidic deprotection of N-Boc-Leu-O-TAGa (4) 3.2. Investigation of hydrophobic tag HO-TAGb (2) 3.2.1. Preparation of N-Boc-Leu-O-TAGb (5) 3.2.2. Acidic deprotection of N-Boc-Leu-O-TAGb (5) 3.3. Investigation of hydrophobic tag HO-TAGc (3) 3.3.1. Preparation of N-Boc-Leu-O-TAGc (6) 3.3.2. Acidic deprotection of N-Boc-Leu-O-TAGc (6) 3.4. Preparation of N-Fmoc-Pro-O-TAGc (10) 3.5. N-Fmoc group deprotection of N-Fmoc-Pro-O-TAGc (10) 3.6. Preparation of N-Boc-Arg(Mts)-Pro-O-TAGc (12) 3.7. N-Boc group deprotection of N-Boc-Arg(Mts)-Pro-O-TAGc (12) 3.8. General method for the elongation of H-Peptide-O-TAGc 3.9. General method for N-Fmoc group deprotection of N-Fmoc-Peptide-O-TAGc 3.10. Acidic deprotection of N-Boc-A-TNF-(Mts)-O-TAGc (15) 3.11. Mts group deprotection of H-A-TNF-(Mts)-OH (S3) 4. Spectra Information Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010