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N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine

  CAS No.: 1342211-31-7   Cat No.: BADC-00454   Purity: ≥98% 4.5  

MC-Val-Ala-OH is a promising dipeptidyl peptidase 4 (DPP-4) inhibitor. It demonstrates the potential to reduce the breakdown of incretin hormones by inhibiting DPP-4. This intervention promotes increases in glucagon-like peptide 1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP) levels, representing a pathway to superior glycemic management.

N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine

Structure of 1342211-31-7

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Molecular Formula
C18H27N3O6
Molecular Weight
381.42
Shipping
Room temperature

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Synonyms
(S)-2-((S)-2-(6-(2,5-dioxo-2H-pyrrol-1(5H)-yl)hexanamido)-3-methylbutanamido)propanoic acid;
IUPAC Name
Canonical SMILES
C[C@@H](C(=O)O)NC(=O)[C@H](C(C)C)NC(=O)CCCCCN1C(=O)C=CC1=O
InChI
InChI=1S/C18H27N3O6/c1-11(2)16(17(25)19-12(3)18(26)27)20-13(22)7-5-4-6-10-21-14(23)8-9-15(21)24/h8-9,11-12,16H,4-7,10H2,1-3H3,(H,19,25)(H,20,22)(H,26,27)/t12-,16-/m0/s1
InChIKey
GSWKJIWKGSPISH-LRDDRELGSA-N
Appearance
Soild powder
Shipping
Room temperature

N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine is a specialized peptide-conjugated compound featuring a unique pyrrole-derived structure linked to a dipeptide, L-valyl-L-alanine. The pyrrole group, with its distinctive reactivity, enhances the chemical and biological properties of this molecule, making it suitable for various applications in drug delivery, bioconjugation, and molecular biology. The dipeptide sequence further imparts specific biochemical properties that can be exploited for selective interactions with cellular targets, providing a versatile platform for therapeutic and research applications.

One of the key applications of N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine is in the design of targeted drug delivery systems. The pyrrole ring can undergo selective interactions with nucleophilic biomolecules, such as thiols in proteins, enabling the targeted attachment of therapeutic agents to cancer cells or other disease sites. The peptide sequence L-valyl-L-alanine enhances the specificity of binding to certain cellular receptors or enzymes, ensuring that the drug is delivered precisely where it is needed. This approach is especially valuable in reducing systemic toxicity and improving the therapeutic index of the drug, providing more effective and less harmful treatments for a variety of diseases, including cancer.

In addition to its drug delivery potential, N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine plays a significant role in peptide-based biomolecular research. By incorporating the pyrrole group, researchers can use this compound to study specific protein-ligand interactions or enzyme activity. The reactive pyrrole moiety can form covalent bonds with proteins or peptides containing reactive thiol groups, allowing for the investigation of protein function, binding kinetics, and structural changes upon binding. This makes it a valuable tool in proteomics, enzyme inhibition studies, and the exploration of new molecular targets for drug discovery.

The compound’s versatility extends to its use in the synthesis of novel peptide conjugates for biomarker detection and diagnostics. By attaching reporter molecules, such as fluorescent dyes or radiolabels, to the N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine structure, it becomes an effective probe for detecting specific biomarkers associated with diseases. The ability to selectively bind to proteins or cells of interest, combined with the reactive nature of the pyrrole group, enhances the sensitivity and specificity of diagnostic assays, enabling the development of advanced imaging techniques and biosensors for early disease detection, particularly in cancer and infectious diseases.

Another important application of N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine is in the creation of enzyme inhibitors or modulators. The pyrrole moiety can interact with catalytic residues or active sites in enzymes, blocking their activity or altering their function. By designing inhibitors based on this structure, it is possible to develop drugs that target specific enzymes involved in disease progression, such as proteases, kinases, or other enzymes critical in cancer, inflammation, or infectious diseases. This application has the potential to lead to more effective and selective therapeutic agents for a wide range of conditions.

Finally, N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine could be utilized in the development of biomaterials for tissue engineering and regenerative medicine. The peptide component enables the formation of biocompatible materials that can promote cell adhesion, growth, and differentiation. The compound could be incorporated into scaffolds, hydrogels, or nanoparticles, providing a tailored environment for tissue regeneration, wound healing, and drug delivery. Its unique chemical structure offers the possibility of designing materials with precise biological functions, opening new possibilities in regenerative medicine and tissue engineering applications.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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