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43
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79955568650
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note
-
Most standard peptide synthesis procedures followed those in the "Synthesis Notes" section of the 2009/2010 Novabiochem catalog.
-
-
-
-
44
-
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0034674535
-
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Either Fmoc*-Hao-OH or Fmoc-Hao-OH was used to introduce the Hao residue. Fmoc*-Hao-OH has been described previously in ref 10b. Fmoc* refers to the 2,7-di- tert -butyl-Fmoc group. This more soluble analogue of the Fmoc group is described in: Stigers, K. D.; Koutroulis, M. R.; Chung, D. M.; Nowick, J. S. J. Org. Chem. 2000, 65, 3858-3860 For details of the preparation of Fmoc-Hao-OH, see the Supporting Information.
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Stigers, K.D.1
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46
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38849117770
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Hood, C. A.; Fuentes, G.; Patel, H.; Page, K.; Menakuru, M.; Park, J. H. J. Pept. Sci. 2008, 14, 97-101
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Park, J.H.6
-
48
-
-
79955568312
-
-
note
-
In the cyclization step, most macrocyclic peptides were synthesized using HCTU/DIEA/DMF. Cyclization using HCTU/DIEA/DMF produces yellowish impurities that remain after deprotection with TFA. When these colored impurities proved difficult to remove by HPLC purification, cyclization was alternatively performed with HBTU/HOBt/N-methylmorpholine/DMF. (15)
-
-
-
-
49
-
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79955564570
-
-
note
-
HPLC analysis of cyclic peptide 8a shows comparable purities of the crude products from cyclization at 0.5 and 10 mM concentrations, indicating that macrocyclization causes no or little polymerization. For details, see Figure S1 in the Supporting Information. If polymers or oligomers were to form under these conditions, the HPLC traces from cyclization at 10 mM would show impurities substantially greater than those at 0.5 mM.
-
-
-
-
51
-
-
79955554019
-
-
note
-
NOEs between the two Hao units cannot be observed due to symmetry.
-
-
-
-
52
-
-
79955556692
-
-
note
-
2O, and the NOEs involving these protons cannot be observed under the conditions of the ROESY experiments.
-
-
-
-
53
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0034010302
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Yao, S.; Howlett, G. J.; Norton, R. S. J. Biomol. NMR 2000, 16, 109-119
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13244253788
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-
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Cohen, Y.1
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-
55
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79955553215
-
-
note
-
δOrn value of 1.3 ppm in a chloroform solution. For details, see ref 10c.
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-
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