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1
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0345059622
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note
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Abbreviations: AAA, amino acid analysis; Alloc, allyloxycarbonyl; Dde, 1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl; DIEA, N,N-diisopropylethylamine; ES-MS, electrospray mass spectroscopy; Fmoc, 9-(fluorenylmethyloxycarbonyl); HATU, O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; HBTU, O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; NMM, N-methylmorpholine; PAL, 5-(4-(aminomethyl)-3,5-dimethoxyphenoxy) valeric acid; PEG-PS, poly(ethylene glycol)-polystyrene graft resin support; pNZ, p-nitrobenzyloxycarbonyl; PS, polystyrene resin support; PyAOP, (7-azabenzotriazol-1-yloxy)tris(pyrrolidino)phosphonium hexafluorophosphate; PyBOP, (benzotriazol-1-yloxy)tris (pyrrolidino)phosphonium hexafluorophosphate; RAFT, regioselectively addressable functionalized template; RP-HPLC, reversed-phase high performance liquid chromatography; SASRIN, 2-methoxy-4-alkoxybenzyl alcohol resin; SPPS, solid-phase peptide synthesis; Suc, succinyl; TASP, template-assembled synthetic protein; Trt, triphenylmethyl (trityl); XAL, 9-amino-xanthen-3-yloxymethyl; Xaa, Xbb, amino acid. Amino acid symbols denote the L-configuration.
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note
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Studies on this cyclization reaction indicated that HATU, PyBOP, and PyAOP are essentially equally efficient in terms of rapidity (total conversion in less than 10 min) and purity (95% by RP-HPLC).
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note
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Amide linkers (e.g., XAL and PAL) are recommended in order to avoid premature cleavage from the resin during the forthcoming Dde removal.
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Detailed structural and functional properties of 5 are currently under investigation in our laboratory and will be the subject of a future report.
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note
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2O:pyridine in DMF.
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