K-(D-1-Nal)-FwLL-NH2 is a high affinity and potent ghrelin receptor inverse agonist (Ki values are 4.9 and 31 nM in COS7 and HEK293T cells, respectively), which blocks ghrelin receptor-mediated Gq- and G13-dependent signaling pathways.
CAT No: R0816
CAS No:1394288-22-2
Synonyms/Alias:K-(D-1-Nal)-FwLL-NH2;1394288-22-2;CHEMBL2170781;(2S)-2,6-diamino-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-naphthalen-1-yl-1-oxopropan-2-yl]hexanamide;L-Lysyl-3-(1-naphthalenyl)-D-alanyl-L-phenylalanyl-D-tryptophyl-L-leucyl-L-leucinamide;1394288-32-4;GLXC-25344;BDBM50396915;AKOS027470298;DA-64682;PD079927;Lys-(D-1-Nal)-Phe-D-Trp-Leu-Leu-NH2;
K-(D-1-Nal)-FwLL-NH2 is a synthetic peptide featuring a strategically modified sequence that incorporates D-1-naphthylalanine alongside conventional amino acid residues. Its design enables unique interactions with biological targets and enhances resistance to enzymatic degradation, making it a valuable asset in peptide-based research. The sequence's combination of hydrophobic and aromatic side chains, as well as its amidated C-terminus, lends it distinctive conformational properties that are of significant interest in the study of peptide structure-activity relationships. As a result, this compound is frequently utilized in investigations relating to receptor binding, peptide-ligand interactions, and the development of novel bioactive peptides.
Receptor binding studies: The sequence of K-(D-1-Nal)-FwLL-NH2 is particularly suited for probing interactions with G protein-coupled receptors (GPCRs) and other peptide-binding proteins. The inclusion of D-1-naphthylalanine, an unnatural aromatic amino acid, can enhance binding affinity and selectivity by introducing steric and electronic effects not present in natural peptides. Researchers employ this peptide as a tool to dissect the molecular determinants of ligand recognition, map binding sites, and elucidate the structural requirements for receptor activation or inhibition.
Peptide structure-activity relationship analysis: The unique residue composition of this peptide makes it an excellent model for investigating how side-chain modifications and backbone stereochemistry influence biological activity. By comparing the functional outcomes of peptides containing D-1-naphthylalanine with those of their L-amino acid counterparts, scientists gain insights into the role of chirality and aromaticity in modulating peptide function. Such studies are instrumental in guiding the rational design of next-generation peptide therapeutics and research probes.
Enzymatic stability assessment: Due to the presence of a D-amino acid and N-terminal modifications, this peptide exhibits increased resistance to proteolytic enzymes compared to conventional sequences. Researchers utilize it to evaluate the impact of stereochemical alterations on peptide degradation pathways, which is critical for optimizing the pharmacokinetic properties of peptide-based agents. These experiments help in designing peptides with enhanced stability for use in challenging biological environments.
Peptide-membrane interaction studies: The amphipathic and aromatic character of the sequence enables detailed exploration of peptide-membrane interactions. Investigators often employ this peptide to characterize how specific side-chain modifications affect membrane affinity, insertion depth, and potential for membrane disruption. Such studies are essential for understanding the mechanisms underlying peptide-mediated transport, antimicrobial activity, or cell-penetrating properties.
Peptide synthesis and analytical method development: Beyond its functional applications, K-(D-1-Nal)-FwLL-NH2 serves as a reference compound in synthetic peptide chemistry. Its sequence complexity and incorporation of noncanonical amino acids provide a robust test case for optimizing solid-phase peptide synthesis protocols, purification strategies, and analytical techniques such as HPLC and mass spectrometry. The peptide's well-defined structure makes it a valuable standard for validating synthesis and characterization workflows in research and industrial laboratories.
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