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. 2004 May 26;101(23):8531–8536. doi: 10.1073/pnas.0308449101

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Copyright © 2004, The National Academy of Sciences

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Fig. 1. — Synthesis of sterol-modified heptapeptides and overview of synthesized peptides. Step a, 1 (1 eq), N,N-diisopropylethylamine (DIEA, 2 eq), chlorotrityl-resin (0.5 eq), CH₂Cl₂, 5 hr, room temperature. Step b, Pd(PPh₃)₄ (0.2 eq), PhSiH₃ (24 eq), CH₂Cl₂, 3 hr, room temperature. Step c, H-Gly-O-sterol (5 or 6, 5 eq), benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 5 eq), DIEA (10 eq), dimethylformamide (DMF), 5 hr, room temperature. Step d, DMF/piperidine 1:4 (vol/vol), twice for 10 min, room temperature. Step e, fluorenylmethoxycarbonyl (Fmoc)-(Xaa)_x-OH (4 eq), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU, 3.6 eq), 1-hydroxybenzotriazole (HOBt, 4.8 eq), DIEA (8 eq), DMF, 1 hr, room temperature. Step f, repetition of steps d and e, using in the last step N-[6(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]caproic acid (NBDaca) or MIC-OH, respectively. NBD, 7-nitrobenz-2-oxa-1,3-diazole.