Cyclo(His-Pro) forms a diketopiperazine ring uniting histidine and proline in a compact cyclic scaffold. The imidazole side chain contributes metal-binding and acid-base properties, while proline enforces conformational rigidity. Researchers use it as a model for endogenous cyclic dipeptides and neuromodulatory motifs. Applications span food chemistry, neurobiochemistry, and cyclic-peptide structure studies.
CAT No: R2707
CAS No:53109-32-3
Synonyms/Alias:Cyclo(his-pro);Cyclo(-His-Pro);53109-32-3;Cyclo(L-His-L-Pro);UNII-Q10817UXVT;Q10817UXVT;L-His-L-Pro-DKP;L,L-cyclo(histidylprolyl);Cyclo(L-histidyl-L-proline);MLS000028694;CHEBI:90039;CYCLO-(L-HISTIDINE-L-PROLINE) INHIBITOR;SMR000058881;(3S,8aS)-3-(1H-Imidazol-4-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8aS)-3-[(1H-imidazol-5-yl)methyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8AS)-3-(1H-IMIDAZOL-5-YLMETHYL)-2,3,6,7,8,8A-HEXAHYDROPYRROLO(1,2-A)PYRAZINE-1,4-DIONE;(3S,8aS)-3-((1H-imidazol-5-yl)methyl)-octahydropyrrolo(1,2-a)pyrazine-1,4-dione;(3S,8aS)-3-((1H-imidazol-5-yl)methyl)hexahydropyrrolo(1,2-a)pyrazine-1,4-dione;(3S,8aS)-3-(1H-Imidazol-4-ylmethyl)hexahydropyrrolo(1,2-a)pyrazine-1,4-dione;(3S,8aS)-3-[(1H-imidazol-5-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione;MFCD00133207;1w1t;Opera_ID_1205;Cyclo(histidyl-proline);Histidylproline diketopiperazine;cyclo[l-histidyl-l-prolyl];CHEMBL188225;SCHEMBL2039884;SCHEMBL12228287;DTXSID90962567;(3S,8aS)-3-((1H-imidazol-4-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;HMS2234D12;CS-6320;DB02414;FC49257;(3S,8AR)-3-(1H-IMIDAZOL-5-YLMETHYL)HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE;HY-101402;NS00069934;G85416;Q27286866;(3S,8aS)-3-(1H-imidazol-5-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;
Cyclo(his-pro), also known as cyclo(L-histidyl-L-proline) or CHP, is a naturally occurring cyclic dipeptide recognized for its unique structural and biochemical properties. As a member of the diketopiperazine family, Cyclo(his-pro) is formed by the cyclization of the amino acids histidine and proline, resulting in a stable ring structure that imparts significant resistance to enzymatic degradation. This stability, combined with its ability to interact with various biological targets, makes CHP a valuable compound for a wide range of research applications. The molecule's amphipathic nature allows it to traverse biological membranes, further enhancing its utility in experimental settings. Researchers are increasingly interested in Cyclo(his-pro) due to its occurrence in both plant and animal tissues, where it is believed to participate in diverse physiological processes. Its relatively simple synthesis and compatibility with a variety of analytical techniques contribute to its growing prominence in biochemical and pharmacological studies.
Neurochemical Research: In neurochemical investigations, Cyclo(his-pro) is frequently employed as a model compound for studying peptide neurotransmission and modulation. Its presence in brain tissue and association with neuroactive pathways have prompted scientists to explore its potential role in synaptic communication and neuronal regulation. CHP is often used in studies aiming to elucidate the mechanisms underlying peptide-mediated signaling, including its interaction with neurotransmitter systems such as dopamine and acetylcholine. By serving as a tool to probe these pathways, Cyclo(his-pro) aids in advancing the understanding of neural function and the molecular basis of neurochemical balance.
Antioxidant Mechanisms: Researchers utilize Cyclo(his-pro) to investigate its capacity to modulate oxidative stress responses in various biological systems. Due to its inherent chemical structure, CHP can scavenge reactive oxygen species and may influence antioxidant defense pathways. Studies often focus on its effects in cellular models subjected to oxidative challenges, where the compound's ability to regulate redox homeostasis is assessed. These investigations contribute to a deeper comprehension of how cyclic dipeptides can impact cellular resilience and defense mechanisms against oxidative damage.
Cellular Signaling Pathways: Cyclo(his-pro) is a valuable probe in the exploration of intracellular signaling cascades. Its interactions with specific receptors and enzymes, such as those involved in cyclic nucleotide pathways, are of particular interest. By modulating the activity of key signaling molecules, CHP helps clarify the roles of cyclic dipeptides in cellular communication and regulation. Researchers employ this compound to dissect the intricacies of second messenger systems, protein phosphorylation events, and gene expression modulation, thereby expanding knowledge of cell biology and molecular signaling networks.
Nutritional Biochemistry: In the field of nutritional science, Cyclo(his-pro) is studied for its occurrence in food sources and its potential impact on nutrient absorption and metabolism. Scientists analyze its formation during food processing and digestion, as well as its interactions with other dietary components. CHP serves as a marker for peptide content in certain food matrices and is evaluated for its possible influence on gut physiology and metabolic health. These applications support ongoing efforts to understand the bioactive roles of dietary peptides and their contributions to overall wellness.
Peptide Transport Studies: CHP is frequently used in research focused on the mechanisms of peptide transport across biological membranes, particularly within the gastrointestinal tract and the blood-brain barrier. Its stability and amphipathic nature make it an ideal candidate for studying peptide uptake, efflux, and translocation. Investigations often utilize labeled or modified forms of Cyclo(his-pro) to track its movement and distribution in vitro and in vivo, providing critical insights into the factors that govern peptide bioavailability and tissue targeting.
Ongoing research into Cyclo(his-pro) continues to reveal new dimensions of its functionality and versatility. Its unique structure and biological compatibility position it as an indispensable tool in neurochemical research, antioxidant studies, cellular signaling investigations, nutritional biochemistry, and peptide transport analysis. As scientists delve deeper into the molecular interactions and physiological roles of cyclic dipeptides, CHP remains at the forefront of experimental innovation, driving progress in multiple scientific disciplines and fostering a greater understanding of peptide-based processes in living systems.
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