Benzenepentanoic acid → L-Alanine

Participants

Reaction Steps

An analogous procedure to that described in Example 2.6 was used, except that the whole of the peptide assembly was performed manually using HBTU/DIPEA activation, coupling Fmoc-Papa-OH, Fmoc-Ala-OH, Fmoc-Arg(Pbf)-OH, Fmoc-IIb-OH and 5-phenylvaleric acid in the appropriate order. The peptide was cleaved from the resin using a similar procedure to that described in Example 2.6. The product was purified using preparative RP-HPLC in a similar manner to that described for Example 1.4, eluting with a gradient of acetonitrile-water containing 0.1% TFA (15-30% acetonitrile) over 90 minutes at a flow rate of 10 ml/minute. The product was characterised by HPLC, mass spectroscopy and amino acid analysis in a similar manner to that described for Example 1.4; RP-HPLC (eluting with acetonitrile and water containing 0.1% TFA, using a 15-30% acetonitrile gradient over 30 minutes, flow rate 1.0 ml/minute) retention time=20.02 minutes; mass spectrometry, m/e (ES+) 1061.6 (MH+), 531.4 (M+2H++); amino acid analysis gave Ala 4.16, Arg 2.00, IIb present.

Provenance & Evidence