. Author manuscript; available in PMC: 2018 Nov 22.

Published in final edited form as: Org Biomol Chem. 2017 Nov 22;15(45):9595–9598. doi: 10.1039/c7ob02562a

Table 1.

Sequences of bicyclic peptides and their inhibitory activities against TCPTP and PTP1B

Peptide No.	Sequence^a	CPP	IC₅₀ (nM)
Peptide No.	Sequence^a	CPP	TCPTP	PTP1B
1	Pro-Tyr-Ala-F₂Pmp-Pip	I	ND	ND
2	Pro-Ile-Asp-F₂Pmp-Pip	J	ND	ND
3	Asp-Asp-thr-F₂Pmp-Pip	J	ND	ND
4	Asp-glu-Asp-F₂Pmp-Ile	J	550 ± 140	1200 ± 700
5	Gln-Asp-Abu-F₂Pmp-Ala	C	660 ± 280	1750 ± 260
6	Gln-Asp-Phe-F₂Pmp-Ala	J	470 ± 70	1190 ± 30
7	Gln-Asp-Ile-F₂Pmp-Ala	J	340 ± 50	1150 ± 490
8	Gln-Asp-Val-F₂Pmp-Ala	J	380 ± 110	580 ± 70
9	Gln-Asp-Ala-F₂Pmp-Ala	J	1110 ± 70	1430 ± 40
10	Gln-Asp-Ser-F₂Pmp-Ala	J	530 ± 40	840 ± 10
11	Gln-Asp-Nva-F₂Pmp-Ala	J	610 ± 280	1320 ± 250
12	Gln-Asp-Nle-F₂Pmp-Ala	J	580 ± 100	1100 ± 60
13	Gln-Asp-Ile-F₂Pmp-Abu	I	400	1600
14	Gln-Asp-Ile-F₂Pmp-Ile	J	240	500
15	Gln-Asp-Ile-F₂Pmp-Val	J	420	730
16	Gln-Asp-Ile-F₂Pmp-thr	J	>2000	>2000
17	Gln-Asp-Ile-F₂Pmp-Gln	J	210 ± 50	590 ± 260
18	Gln-Asp-Ile-F₂Pmp-Asn	J	380 ± 5	910 ± 410
19	Gln-Asp-Ile-F₂Pmp-Nle	J	290 ± 120	840 ± 150
20	Gln-Asp-Ile-F₂Pmp-Leu	J	140 ± 40	260 ± 60
21	Gln-Asp-Ile-F₂Pmp-Tle	J	680 ± 140	560 ± 90
22	Gln-glu-Ile-F₂Pmp-Leu	J	1120	1270
23	Gln-asp-Ile-F₂Pmp-Leu	J	1090	1340
24	Gln-phe-Ile-F₂Pmp-Leu	J	250	530
25	Gln-Fpa-Ile-F₂Pmp-Leu	J	110 ± 16	420 ± 200
26	Gln-Glu-Ile-F₂Pmp-Leu	J	250	410
27	Gln-Tyr-Ile-F₂Pmp-Leu	J	140	210
28	Ala-Fpa-Ile-F₂Pmp-Leu	J	140 ± 10	280 ± 2
29	Pro-Fpa-Ile-F₂Pmp-Leu	J	140 ± 20	290 ± 70
30	glu-Fpa-Ile-F₂Pmp-Leu	J	47 ± 3	46 ± 17
31	Phg-Fpa-Ile-F₂Pmp-Leu	J	310 ± 230	350 ± 240
32	ser-Fpa-Ile-F₂Pmp-Leu	J	140 ± 40	100 ± 20
33	Gln-Fpa-Ile-Tyr-Leu	J	ND	ND

Only the randomized region is shown. Three-letter codes in all lowercase letters indicate D-amino acids. ND, not determined due to no significant inhibition.