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. Author manuscript; available in PMC: 2007 Apr 12.
Published in final edited form as: Chem Biol Drug Des. 2006 May;67(5):329–335. doi: 10.1111/j.1747-0285.2006.00383.x

Table 1.

Sequences and the physicochemical properties of the cyclic α-MSH analogs

m/z (M + 1)
TLC Rfb
No. Sequence Calculated Observed (ESI) HPLC retention time (min)a 1 2 3
1 c[CO-m-C6H4-CO-His-D-Phe-Arg-Trp-Lys]-NH2 902.4426 902.4440 14.12 0.56 0.10 0.68
2 c[CO-p-C6H4-CO-His-D-Phe-Arg-Trp-Lys]-NH2 902.4426 902.4518 15.26 0.53 0.04 0.61
3 c[CO-2,6-pyridine-CO-His-D-Phe-Arg-Trp-Lys]-NH2 903.4378 903.4237 14.37 0.64 0.11 0.67
4 c[CO-2,3-pyrazine-CO-His-D-Phe-Arg-Trp-Lys]-NH2 904.4331 904.4195 14.38 0.58 0.04 0.60
5 c[CO-cis-CH=CH-CO-His-D-Phe-Arg-Trp-Lys]-NH2 852.4269 852.4312 12.87 0.63 0.05 0.66
6 c[CO-(CH2)4-CO-His-D-Phe-Arg-Trp-Lys]-NH2 882.4739 882.4685 12.39 0.61 0.05 0.63
7 c[CO-(CH2)5-CO-His-D-Phe-Arg-Trp-Lys]-NH2 896.4895 896.4908 12.46 0.65 0.06 0.65
8 c[CO-m-C6H4-CO-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 952.4582 952.4563 16.50 0.71 0.11 0.70
9 c[CO-p-C6H4-CO-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 952.4582 952.4618 16.98 0.62 0.06 0.69
10 c[CO-2,6-pyridine-CO-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 953.4535 953.4491 16.52 0.71 0.14 0.69
11 c[CO-2,3-pyrazine-CO-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 954.4487 954.4502 15.21 0.41 0.07 0.69
12 c[CO-cis-CH=CH-CO-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 902.4426 902.4474 14.63 0.66 0.06 0.69
13 c[CO-(CH2)4-CO-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 932.4895 932.4916 14.42 0.64 0.05 0.66
14 c[CO-(CH2)5-CO-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 946.5052 946.4997 14.23 0.69 0.11 0.68
15 H-c[Glu-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 933.4848 933.4884 13.33 0.55 0.03 0.59
16 Ac-c[Glu-His-D-Nal(2′)-Arg-Trp-Lys]-NH2 975.4952 975.4921 15.51 0.63 0.06 0.67

α-MSH, α-melanocyte-stimulating hormone; HPLC, high-performance liquid chromatography; TLC, thin-layer chromatography; ESI, electrospray ionization.

a

HPLC column: Vydac 218TP104, 250 × 4.6 mm, 10 μm, 300 Å; HPLC solvent A, 0.1% trifluoroacetic acid in water; solvent B, acetonitrile; gradient: 10–90% B in A over 40 min, flow rate 1.0 mL/min.

b

TLC system 1: ethyl acetate/acetic acid/water/pyridine (5:1:3:5); TLC system 2: n-propanol/acetic acid/water (10:1:1); TLC system 3: n-butanol/acetic acid/water/pyridine (5:1:4:5).