Conformational searching, computer simulations, synthesis and NMR are used on a variety of α melanocyte-stimulating hormone (α-MSH) analogues to understand the physical characteristics required for biological potency. Peptides I (Ac-[Nle4,Asp5,D-Phe7,Lys10]α-MSH(4-10)-NH2), II (Ac- c[Nle4,Asp5,D-Phe7,Lys10]α-MSH(4-10)-NH2) and III (Ac-[Nle4,Asp5,D- Phe7,Dap10]α-MSH(4-10)-NH2 all show very similar conformational properties (backbone and side-chain torsional angles), and all-display high biological potencies. The modeling results for these compounds are supported by the NMR data. Peptide IV (Ac-c[Nle4,Asp5,D-Phe7,Dap10]α-MSH(4-10)- NH2) appears to have a markedly different conformation and has decreased biological potency.
|Original language||English (US)|
|Number of pages||12|
|Journal||Journal of Peptide Research|
|State||Published - Jun 8 1998|
- Cyclic melanotropins
- Quenched molecular dynamics
ASJC Scopus subject areas