Cyclo(His-Pro) (TFA) forms a diketopiperazine ring incorporating histidine and proline, creating a rigid conformation. Protonated states influence hydrogen bonding and aromatic interactions. Researchers study its behavior across pH conditions. Uses include cyclic-peptide research, structural analysis, and solvent-dependent folding studies.
CAT No: R2690
CAS No:936749-56-3
Synonyms/Alias:Cyclo(his-pro) (TFA);Cyclo(his-pro) TFA;936749-56-3;(3S,8AS)-3-((1H-imidazol-5-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 2,2,2-trifluoroacetate;HY-101402A;MS-25358;CS-0104166;G17293;(3S,8aS)-3-(1H-imidazol-5-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione;2,2,2-trifluoroacetic acid;
Cyclo(his-pro) (TFA), also known as cyclic histidyl-proline trifluoroacetate, is a synthetic cyclic dipeptide composed of the amino acids histidine and proline. As a stable diketopiperazine, it exhibits unique conformational rigidity and distinct biochemical properties, making it an important molecule for research in peptide chemistry, neurobiology, and cellular signaling. Its cyclic structure imparts resistance to enzymatic degradation and enables it to participate in specific molecular recognition processes, which has spurred interest in its functional roles in biological systems and its utility as a model compound for studying peptide cyclization and stability.
Peptide structure-function studies: Due to its well-defined cyclic conformation, Cyclo(his-pro) (TFA) serves as a valuable model for investigating the relationship between peptide structure and biological activity. Researchers utilize it to explore how cyclization affects peptide stability, receptor binding, and resistance to proteolytic enzymes. Its use in such studies helps elucidate the principles governing peptide folding and the impact of conformational constraints on molecular function, thereby informing the design of novel cyclic peptides with tailored properties for biochemical applications.
Biochemical mechanism elucidation: Cyclo(his-pro) is employed in experimental systems to probe the mechanisms of diketopiperazine formation and metabolism. Its defined structure provides an exemplary substrate for studying enzymatic processes involved in cyclic dipeptide biosynthesis and degradation. Investigations using this compound contribute to a deeper understanding of peptide bond cyclization, the role of diketopiperazines in metabolic pathways, and the enzymology underlying peptide modifications in both prokaryotic and eukaryotic organisms.
Neurobiological research: The cyclic dipeptide is of particular interest in neurochemical studies, as it has been identified as a naturally occurring metabolite in mammalian tissues, especially within the central nervous system. Scientists employ Cyclo(his-pro) to investigate its potential regulatory roles in neurotransmitter systems, neuronal signaling, and synaptic modulation. Its application in in vitro and ex vivo models aids in clarifying how small cyclic peptides can influence neural communication and modulate biochemical pathways relevant to brain function.
Analytical standard and reference material: Owing to its chemical stability and well-characterized properties, Cyclo(his-pro) (TFA) is frequently used as a reference standard in analytical chemistry. Laboratories utilize it to calibrate chromatographic methods, validate mass spectrometry assays, and benchmark peptide quantification protocols. Its consistent performance as a standard supports the development of robust analytical techniques for peptide detection and characterization in complex biological samples.
Peptide synthesis optimization: The compound is also employed as a benchmark in synthetic peptide chemistry, where it serves as a model for optimizing cyclization strategies and improving yields of cyclic peptides. Researchers leverage its synthesis to refine solid-phase and solution-phase cyclization protocols, evaluate protecting group strategies, and study the influence of reaction conditions on diketopiperazine formation. Insights gained from work with Cyclo(his-pro) inform best practices for the synthesis of structurally related cyclic peptides, advancing the field of peptide engineering and chemical biology.
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