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. Author manuscript; available in PMC: 2017 Nov 6.
Published in final edited form as: J Med Chem. 2015 Apr 21;58(11):4638–4647. doi: 10.1021/acs.jmedchem.5b00184

Table 1.

Analytical Data for the Peptides Synthesized in This Studya

Peptide Structure HPLC k′ (system 1) HPLC k′ (system 2) M+1 (calcd) mass spectral analysis (M+1), purity %
1 graphic file with name nihms913780t1.jpg 5.9 10.6 1771.8 1771.9 (>98%)
2 graphic file with name nihms913780t2.jpg 5.6 10.7 1831.8 1831.9 (>98%)
3 graphic file with name nihms913780t3.jpg 5.5 10.5 1833.7 1832.9 (>98%)
4 c[Pro-Tyr-Ala-Arg-Phe-Phe-Asn-Ala-Phe-Ala-Tyr-DPro] 7.7 12.9 1445.7 1445.6 (>98%)
5 c[Pro-Tyr-Thr-Arg-Phe-Phe-Asn-Ala-Phe-Thr-Tyr-DPro] 7.9 13.5 1505.7 1505.6 (>98%)
6 c[Pro-Arg-Phe-Phe-Asn-Ala-Phe-DPro] 7.4 5.5 977.5 977.6 (>95%)
7 c[Pro-Arg-Bip-Phe-Asn-Ala-Phe-DPro] 9.0 15.0 1054.2 1053.6 (>95%)
8 c[Pro-Arg-Tic-Phe-Asn-Ala-Phe-DPro] 7.2 12.6 990.1 990.3 (>98%)
9 c[Pro-Arg-Phg-Phe-Asn-Ala-Phe-DPro] 7.0 11.9 964.1 964.3 (>98%)
10 c[Pro-Arg-hPhe-Phe-Asn-Ala-Phe-DPro] 7.9 13.3 992.1 991.5 (>95%)
11 c[Pro-Arg-Anc-Phe-Asn-Ala-Phe-DPro] 7.7 12.6 1000.1 1000.0 (>95%)
12 c[Pro-Arg-Nal(1′)-Phe-Asn-Ala-Phe-DPro] 8.4 14.1 1028.2 1027.8 (>98%)
13 c [Pro-Arg-Nal(2′)-Phe-Asn-Ala-Phe-DPro] 8.5 14.5 1028.2 1028.0 (>98%)
14 c[Pro-Arg-Phe-Bip-Asn-Ala-Phe-DPro] 8.6 15.1 1054.2 1057.1 (>95%)
15 c[Pro-Arg-Phe-Tic-Asn-Ala-Phe-DPro] 8.3 13.0 990.1 989.2 (>98%)
16 c[Pro-Arg-Phe-Phg-Asn-Ala-Phe-DPro] 6.9 11.9 964.1 964.2 (>98%)
17 c[Pro-Arg-Phe-hPhe-Asn-Ala-Phe-DPro] 7.9 13.5 992.1 991.6 (>95%)
18 c[Pro-Arg-Phe-Anc-Asn-Ala-Phe-DPro] 8.3 13.1 1000.1 999.8 (>95%)
19 c[Pro-Arg-Phe-Nal(1′)-Asn-Ala-Phe-DPro] 8.3 14.4 1028.2 1028.1 (>98%)
20 c[Pro-Arg-Phe-Nal(2′)-Asn-Ala-Phe-DPro] 8.5 14.2 1028.2 1028.2 (>98%)
21 c[Pro-Arg-Phe-Phe-Gly-Ala-Phe-DPro] 7.7 5.9 920.5 920.8 (>98%)
22 c[Pro-Arg-Phe-Phe-Dap-Ala-Phe-DPro] 3.2 5.6 949.6 950.0 (>98%)
23 c[Pro-Arg-Phe-Phe-Dab-Ala-Phe-DPro] 6.9 5.6 963.5 964.4 (>98%)
24 c[Pro-Arg-Phe-Phe-Orn-Ala-Phe-DPro] 7.1 5.5 977.6 977.9 (>95%)
25 c[Pro-Arg-Phe-Phe-Lys-Ala-Phe-DPro] 7.1 5.5 991.6 991.9 (>95%)
26 c[Pro-Arg-Phe-Phe-Arg-Ala-Phe-DPro] 7.2 12.6 1019.6 1020.5 (>98%)
a

HPLC k′ = [(peptide retention time – solvent retention time)/solvent retention time] in solvent system 1 (10% acetonitrile in 0.1% trifluoroacetic acid/water and a gradient to 90% acetonitrile over 35 min) or solvent system 2 (10% methanol in 0.1% trifluoroacetic acid/water and a gradient to 90% methanol over 35 min). An analytical Vydac C18 column (Vydac 218TP104) was used with a flow rate of 1.5 mL/min. The peptide purity was determined by HPLC at a wavelength of 214 nm.