Alamandine

Alamandine is a heptapeptide belonging to the renin-angiotensin family, exhibiting distinct structural motifs that influence receptor-binding landscapes. Its sequence combines aromatic, charged, and aliphatic residues, supporting studies of helix formation and solvent-driven conformational shifts. Researchers use it to investigate peptide-membrane interactions and molecular recognition mechanisms. Its well-defined architecture aids advanced biophysical analysis.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Alamandine(CAS 1176306-10-7)

CAT No: PI-016

CAS No:1176306-10-7

Synonyms/Alias:alamandine;1176306-10-7;Ala-Arg-Val-Tyr-Ile-His-Pro;(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carboxylic acid;L-Alanyl-L-arginyl-L-valyl-L-tyrosyl-L-isoleucyl-L-histidyl-L-proline;GTPL6065;CHEBI:190281;HY-P3108;AKOS040755865;DA-70667;MS-31578;CS-0145495;C20971;G17776;

Chemical Name:(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carboxylic acid

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M.F/Formula
C40H62N12O9
M.W/Mr.
855
Sequence
One Letter Code:ARVYIHP
Three Letter Code:H-Ala-Arg-Val-Tyr-Ile-His-Pro-OH

Alamandine is a biologically active peptide belonging to the renin-angiotensin system (RAS), characterized by its seven-amino-acid sequence and structural similarity to angiotensin (1-7). As a heptapeptide, it has garnered significant attention in biochemical and physiological research due to its distinct receptor interactions and regulatory effects on vascular and cellular signaling pathways. Alamandine's ability to interact with the Mas-related G protein-coupled receptor D (MrgD) distinguishes it from other RAS peptides, positioning it as a valuable tool for investigating alternative RAS axis mechanisms. Its study has provided new perspectives on the modulation of cardiovascular, renal, and metabolic processes, making it a compound of interest in peptide biochemistry and signaling research.

Peptide receptor characterization: Alamandine is widely used in studies aimed at elucidating the binding specificity and downstream signaling of the MrgD receptor. By employing this peptide in receptor-ligand assays, researchers can dissect the pharmacological properties and activation profiles of MrgD, as well as compare its functional outcomes to those of other RAS-related peptides. This application is essential for mapping receptor selectivity and understanding the broader implications of alternative RAS pathways in cellular physiology.

Signal transduction analysis: The peptide serves as a robust molecular tool for probing intracellular signaling cascades initiated by non-canonical RAS ligands. Investigations utilizing alamandine enable scientists to delineate pathways such as nitric oxide production, cyclic GMP accumulation, and kinase activation in various cell types. These studies are instrumental in clarifying how peptide-mediated modulation of second messenger systems influences cell function and homeostasis.

Vascular function research: Alamandine is frequently applied in experimental models to assess its effects on vascular tone, endothelial function, and smooth muscle cell behavior. By examining its actions in isolated vessel preparations or cultured vascular cells, researchers can evaluate its capacity to induce vasodilation, modulate oxidative stress, or influence inflammatory mediators. Such studies contribute to a deeper understanding of the regulatory networks controlling vascular reactivity and integrity.

Metabolic regulation studies: Due to its emerging role in energy homeostasis and metabolic signaling, alamandine is utilized to investigate its influence on glucose uptake, lipid metabolism, and adipocyte differentiation in cellular and tissue-based assays. These applications help clarify the peptide's contribution to metabolic balance and provide insights into the interplay between RAS components and metabolic pathways, particularly in the context of obesity and insulin sensitivity.

Peptide structure-activity relationship (SAR) analysis: Alamandine's unique sequence and bioactivity make it an excellent reference compound for SAR studies within the angiotensin peptide family. Researchers employ it to evaluate how specific amino acid substitutions or modifications affect receptor binding, biological activity, and stability. Such investigations facilitate the rational design of novel peptide analogs with tailored pharmacological profiles, advancing the development of research tools for dissecting RAS function and peptide signaling mechanisms.

InChI
InChI=1S/C40H62N12O9/c1-6-22(4)32(37(58)49-29(18-25-19-44-20-46-25)38(59)52-16-8-10-30(52)39(60)61)51-35(56)28(17-24-11-13-26(53)14-12-24)48-36(57)31(21(2)3)50-34(55)27(47-33(54)23(5)41)9-7-15-45-40(42)43/h11-14,19-23,27-32,53H,6-10,15-18,41H2,1-5H3,(H,44,46)(H,47,54)(H,48,57)(H,49,58)(H,50,55)(H,51,56)(H,60,61)(H4,42,43,45)/t22-,23-,27-,28-,29-,30-,31-,32-/m0/s1
InChI Key
QVMYBFKDLPBYSO-GIGALADGSA-N
Canonical SMILES
CCC(C)C(C(=O)NC(CC1=CN=CN1)C(=O)N2CCCC2C(=O)O)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C(C(C)C)NC(=O)C(CCCN=C(N)N)NC(=O)C(C)N
Isomeric SMILES
CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)N2CCC[C@H]2C(=O)O)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](C)N

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