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Interestingly, we obtained better coupling of Fmoc*-Hao using DCC and HOBt than using HATU or HATU and HOAt, which are often better peptide coupling agents. For descriptions of HATU and HOAt, see: Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
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0343626652
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note
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Our experiences suggest that the coupling of Hao is slightly less efficient than that of ordinary amino acids. Double coupling was performed in each step in the synthesis to ensure complete reaction, although it was not clear that it was required.
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42
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0011667653
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0343191101
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note
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2 → i-PrCO-Phe-Hao-NHR). This exceptional reactivity of Hao ester derivatives also allows their facile base-promoted hydrolysis and transesterification.
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0342756397
-
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note
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tot was calculated from the volumes and concentrations of the solutions used in the titration.
-
-
-
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51
-
-
0343626650
-
-
note
-
bound were calculated to be 4.83 and 5.26 ppm, respectively.
-
-
-
-
52
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0342756395
-
-
note
-
Interestingly, peptide derivative 9 shows a strong propensity to form dimers in the electrospray mass spectrum, and the relative intensities of the dimer and monomer peaks correlate with the concentration of 9 introduced into the spectrometer.
-
-
-
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53
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0342756396
-
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note
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3 solution.
-
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54
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0031882011
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5244370033
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61
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0342321561
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note
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2.
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