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. Author manuscript; available in PMC: 2008 May 2.
Published in final edited form as: J Med Chem. 2007 May 22;50(12):2779–2786. doi: 10.1021/jm061369n

Table 1.

Sequence and Analytical Data of Bifunctional Peptide Ligands

m/za (M + H)+
 HPLCb log k
 TLCc (Rf)
no. sequence obsd (ESI) calcd (A) (B) (I) (II) (III)
1 H-Tyr-d-Ala-Gly-Phe-Phe-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY003) 1226.5139 1226.5151 20.12 11.75 0.16 0.77 0.82
2 H-Tyr-d-Ala-Gly-Phe-d-Phe-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY007) 1226.5127 1226.5151 20.95 13.26 0.19 0.72 0.88
3 H-Tyr-d-Ala-Gly-Phe-Gly-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY006) 1136.4745 1136.4681 18.46 10.16 0.04 0.45 0.72
4 H-Tyr-d-Ala-Gly-Phe-Leu-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY004) 1192.5286 1192.5307 19.51 11.42 0.23 0.81 0.79
5 H-Tyr-d-Ala-Gly-Phe-Met-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY005) 1210.4810 1210.4871 19.21 11.14 0.14 0.73 0.79
6 H-Tyr-d-Ala-Gly-Phe-Met(O)-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY023) 1226.4786 1226.4820 16.91 9.49 0.06 0.44 0.62
7 H-Tyr-d-Ala-Gly-Phe-Nle-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY018) 1192.5291 1192.5307 19.70 11.64 0.21 0.79 0.82
8 H-Tyr-d-Ala-Gly-Phe-N-Me-Nle-Pro-Leu-Trp-O-3,5-Bzl(CF3)2 (TY019) 1206.5489 1206.5464 19.94 11.94 0.20 0.79 0.85
a

High-resolution mass spectroscopy using electrospray ionization method.

b

HPLC log k′ = log [(peptide retention time — solvent retention time)/solvent retention time]. (A) 10−90% of acetonitrile containing 0.1% TFA within 40 min and up to 95% within additional 5 min, 1 mL/min, (B) 30−70% of acetonitrile containing 0.1% TFA within 20 min and up to 95% within additional 5 min, 1 mL/min.

c

(I) CHCl3:MeOH:AcOH = 90:10:3, (II) EtOAc:n-BuOH:water:AcOH = 5:3:1:1, (III) n-BuOH:water:AcOH = 4:1:1.