CAS 3705-26-8

Cyclo(L-Phe-L-Pro)

Description:

Cyclo(L-Phe-L-Pro), also known as cyclo(L-phenylalanine-L-proline), is a cyclic dipeptide composed of the amino acids phenylalanine and proline. This compound features a cyclic structure that enhances its stability compared to linear peptides. The presence of the phenylalanine residue contributes to its hydrophobic characteristics, while the proline residue introduces a unique rigidity due to its cyclic structure, which can influence the conformation of the peptide. Cyclo(L-Phe-L-Pro) is known for its potential biological activities, including antimicrobial and antioxidant properties, making it of interest in pharmaceutical and biochemical research. Its cyclic nature may also affect its interaction with biological receptors and enzymes, potentially leading to unique pharmacological effects. Additionally, the compound's solubility and stability can vary depending on the pH and solvent conditions, which is crucial for its applications in drug formulation and delivery systems. Overall, cyclo(L-Phe-L-Pro) represents a fascinating area of study in peptide chemistry and its applications in medicinal chemistry.

Formula: C₁₄H₁₆N₂O₂

InChI: InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m0/s1

InChI key: InChIKey=QZBUWPVZSXDWSB-RYUDHWBXSA-N

SMILES: O=C1N2[C@](C(=O)N[C@H]1CC3=CC=CC=C3)(CCC2)[H]

Synonyms:

• (3S,8aS)-3-benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• (3S,8aS)-Hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
• 3-Benzylhexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione
• <span class="text-smallcaps">L</smallcap>-Phenylalanyl-<smallcap>L</span>-proline lactam
• <span class="text-smallcaps">L</smallcap>-Prolyl-<smallcap>L</span>-phenylalanine diketopiperazine
• Cyclo(-Phe-Pro)
• Cyclo(<span class="text-smallcaps">L</smallcap>-Phe-<smallcap>L</span>-Pro)
• Cyclo(<span class="text-smallcaps">L</smallcap>-Pro-<smallcap>L</span>-Phe)
• Cyclo(<span class="text-smallcaps">L</smallcap>-phenylalanyl-<smallcap>L</span>-prolyl-)
• Cyclo(<span class="text-smallcaps">L</smallcap>-prolyl-<smallcap>L</span>-phenylalanyl)
• Maculosin 2
• Maculosine 2
• Pyrrolo[1,2-a]pyrazine-1,4-dione, 3-benzylhexahydro-, (3S,8aS)-
• Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-, (3S,8aS)-
• Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-, (3S-trans)-
• Smfei 02
• (3S-trans)-3-Benzylhexahydropyrrolo(1,2-a)pyrazine-1,4-dione

Cyclo(-Phe-Pro)

CAS: 3705-26-8

Cain et al. obtained an array of small molecule peptide mimetics targeting the melanocortin receptors from this diketopiperazine. Brauns et al. demonstrated that cyclo(Phe-Pro) inhibits the growth of HT-29, MCF-7 and HeLa cells and induces apoptosis in HT-29 colon cancer cells.

Formula: C₁₄H₁₆N₂O₂

Purity: 99.9%

Color and Shape: White Powder

Molecular weight: 244.29

Ref: 01-4029456

Cyclo(-Phe-Pro)

CAS: 3705-26-8

Formula: C₁₄H₁₆N₂O₂

Purity: %

Color and Shape: Solid

Molecular weight: 244.2890

Ref: IN-DA007CC1

Cyclo(L-Phe-L-Pro)

CAS: 3705-26-8

Cyclo(L-Phe-L-Pro)

Purity: ≥98%

Molecular weight: 244.29g/mol

Ref: 54-BUP06663

Cyclo(L-Phe-L-Pro)

CAS: 3705-26-8

Cyclo(L-Phe-L-Pro) shows broad-spectrum antibacterial and antifungal activities.

Formula: C₁₄H₁₆N₂O₂

Purity: 97.08%

Color and Shape: Solid

Molecular weight: 244.29

Ref: TM-TN6672

Cyclo(-Phe-Pro)

CAS: 3705-26-8

Formula: C₁₄H₁₆N₂O₂

Purity: >95.0%(HPLC)

Color and Shape: White to Light yellow powder to crystal

Molecular weight: 244.29

Ref: 3B-C3989

Cyclo(L-phenylalanyl-L-prolyl)

CAS: 3705-26-8

Formula: C₁₄H₁₆N₂O₂

Molecular weight: 244.29

Ref: 4Z-N-0672

Cyclo(L-phenylalanyl-L-prolyl)-d5

CAS: 3705-26-8

Formula: C₁₄H₁₁D₅N₂O₂

Molecular weight: 249.32

Ref: 4Z-N-0674

Cyclo(L-prolyl-L-phenylalanyl)

CAS: 3705-26-8

Applications Cyclo(L-prolyl-L-phenylalanyl) is a diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus.
References Sansinenea, E., et al.: Tetrahedron Lett., 57, 2604 (2016)

Formula: C₁₄H₁₆N₂O₂

Color and Shape: Neat

Molecular weight: 244.29

Ref: TR-C988180

Cyclo(-Phe-Pro)

CAS: 3705-26-8

Cyclo-Phe-Pro is an intermolecular hydrogen bond that has been shown to inhibit the growth of viruses. Cyclo-Phe-Pro binds to the hydrophobic region on viral capsid proteins and inhibits their uptake into cells, which may be due to its ability to form hydrogen bonds with the amino acid serine in these proteins. It also has antimicrobial activity against a number of bacterial species and can be used as a pre-preparation for high performance liquid chromatography (HPLC).

Formula: C₁₄H₁₆N₂O₂

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 244.29 g/mol

Ref: 3D-FC49481

Cyclo(-Phe-Pro)

CAS: 3705-26-8

Formula: C₁₄H₁₆N₂O₂

Purity: 98+%

Molecular weight: 244.294

Ref: 10-F493202