Synonym |
Cyclo(Phe-Phe) |
Species |
Human |
Protein Accession |
NA |
Purity |
≥98% |
Endotoxin Level |
<0.1 EU/μg |
Biological Activity |
NA |
Expression System |
Chemical synthesis |
Fusion Tag |
NA |
Predicted Molecular Mass |
538.59 Da |
Formulation |
Supplied as a lyophilized powder |
Reconstitution |
Reconstitute in sterile water |
Storage & Stability |
Store at -20°C. Stability: ≥ 2 years |
FAQ
What is Cyclo(Phe-Phe) and how is it beneficial in scientific research or practical
applications?
Cyclo(Phe-Phe), also known as cyclo-dipeptide or diketopiperazine (DKP), is a
cyclic dimer of the amino acid phenylalanine. It is classified under cyclic dipeptides, which are the
smallest possible peptides that form a cyclic structure. These molecules are of great interest in
scientific research due to their unique structural and functional properties. The cyclical nature of
Cyclo(Phe-Phe) imparts it with a stability that is often superior to linear peptides, making it an
attractive candidate for various applications.
The compound has been studied for its potential
use in pharmaceutical developments, particularly due to its structural mimicry of biologically active
peptides. This mimicry allows Cyclo(Phe-Phe) to engage in interactions similar to natural peptides,
potentially enabling the modulation of biological processes. It has shown promise in antimicrobial
activity, providing a pathway for the development of novel antibiotics at a time when antibiotic
resistance is a growing concern globally. The mechanism often involves disruption of bacterial cell
walls or inhibiting essential enzymes, thus arresting microbial proliferation.
In food sciences,
Cyclo(Phe-Phe) is researched for its natural occurrence and potential impact on taste and texture. The
compound is sometimes produced during fermentation and has been linked to umami taste sensations.
Understanding its role can lead to enhancements in food flavor and the development of new culinary
products that are both healthful and appealing.
Moreover, the chemical characteristics of
Cyclo(Phe-Phe) make it a suitable probe in structural biology. Its stable cyclic structure is used to
design biomimetic materials, facilitate the study of protein-protein interactions, and even as templates
in the synthesis of more complex peptides. Its structural integrity aids in illustrating folding
pathways of proteins, making it quintessential in enhancing the comprehension of protein
dynamics.
Perhaps one of the most fascinating aspects of Cyclo(Phe-Phe) is its role in
nanotechnology and materials science. Researchers have explored its self-assembling properties to create
nanoscale materials with potential applications in drug delivery systems, where its carrier properties
are harnessed to improve the solubility, stability, and bioavailability of drugs. The small, cyclical
nature of the compound makes it an efficient building block for such sophisticated, precisely-tuned
systems.
In sum, Cyclo(Phe-Phe) is increasingly recognized as a versatile molecular scaffold with
broad applications spanning from medicinal chemistry to materials science, food technology, and beyond.
Its balance of stability and functionality presents continuous opportunities for innovation and
discovery in various scientific arenas.
How is Cyclo(Phe-Phe) synthesized in a laboratory
setting?
Cyclo(Phe-Phe) synthesis in the laboratory is typically achieved through the cyclization
of dipeptides derived from phenylalanine. This process can be conducted using several well-established
synthetic strategies, each with its own advantages and considerations. One common approach is through
solid-phase peptide synthesis (SPPS), a widely used technique particularly suited for creating cyclic
peptides like Cyclo(Phe-Phe).
In SPPS, the synthesis begins with its linear precursor, typically
involving the step-wise addition of protected amino acids to a solid support. For Cyclo(Phe-Phe), two
phenylalanine residues are sequentially coupled, utilizing protecting groups like Boc
(tert-butyloxycarbonyl) or Fmoc (9-fluorenylmethoxycarbonyl) to prevent premature reactions and side
chain interactions during synthesis. Following the construction of the linear dipeptide on the solid
resin, a cyclization step is typically induced by activating the terminal amino and carboxyl groups,
enabling an intramolecular amide bond to form, which results in the cyclic structure of
Cyclo(Phe-Phe).
Cyclization is often regarded as a critical step due to its impact on yield and
purity. Various coupling reagents such as HOBt (1-hydroxybenzotriazole) or PyBOP
(benzotriazole-l,1,3,3-tetramethyluronium hexafluorophosphate) can be used to facilitate this process.
Cyclization can be sensitive to several factors, including concentration, reaction time, and solvent
system. As such, optimizing these parameters is essential to minimizing side reactions, such as
oligomerization, which can significantly affect the purity and yield.
Liquid-phase peptide
synthesis is another viable option for Cyclo(Phe-Phe) synthesis. This approach provides easier
monitoring of reaction progress and potential impurities, offering significant advantages in
purification processes. However, it tends to involve more extensive work-up steps and higher solvent
usage compared to SPPS.
In recent years, advancements in green chemistry also enable the
environmentally-friendly synthesis of Cyclo(Phe-Phe). Methods such as microwave-assisted synthesis or
the use of enzyme catalysis offer promising routes that are not only efficient but also minimize
hazardous waste.
In the laboratory, verification of the synthesized Cyclo(Phe-Phe) is crucial,
typically involving various analytical techniques. Techniques such as HPLC (High Performance Liquid
Chromatography) and mass spectrometry are often utilized to confirm the purity and molecular weight
respectively, whereas NMR (Nuclear Magnetic Resonance) can provide insightful data on the compound's
structure.
Each synthesis method's ultimate goal is to achieve a high-purity product, which can
then be utilized in its respective application, be it in research or practical applications, and thus
serves as a testament to the continual innovation and execution required in peptide synthesis
methodologies.
What safety protocols should be followed when working with Cyclo(Phe-Phe) in the
lab?
Safety is paramount when conducting experiments involving chemical compounds, including
Cyclo(Phe-Phe). Adequate knowledge of the material's properties, proper handling procedures, and
appropriate lab protocols are essential to minimizing risks and ensuring a safe working
environment.
Firstly, obtaining accurate material safety data sheets (MSDS) specific to
Cyclo(Phe-Phe) is necessary. These documents provide comprehensive safety information, including
potential hazards, handling precautions, and first-aid measures. While Cyclo(Phe-Phe) itself may not
possess significant inherent risks, impurities, and solvents used in its synthesis can introduce hazards
requiring careful management.
Personal protective equipment (PPE) is a frontline defense against
potential exposure and accidents. Standard PPE in the lab environment includes lab coats, gloves made of
compatible materials, and safety goggles. Depending on the setting and process involved, using a dust
mask or a respirator may be advised, particularly if there's a risk of inhalation of dust or volatile
components.
Understanding and implementing safe handling practices is crucial. Manipulations of
Cyclo(Phe-Phe) should typically occur in well-ventilated areas, such as a fume hood, to prevent
inhalation risks. The equipment and instrumentation used should be free of contamination, regularly
checked, and serviced to ensure correct functionality, mitigating mishaps.
Given the chemical
processes involved, spill management and accident procedures should be well-understood by all lab
personnel. This includes proficiency in using spill kits, identifying emergency exits and equipment, and
knowing the location and operation of safety showers and eyewash stations. Conducting regular safety
drills or training sessions can help ensure readiness in the case of an actual
emergency.
Disposal of Cyclo(Phe-Phe) and related lab waste must align with institutional and
regulatory guidelines. Depending on the reagents involved, waste may need to be categorized and disposed
of as hazardous material. This not only applies to remnants of Cyclo(Phe-Phe) but also to any solvents
or solvents mixtures used during the experiment, highlighting the importance of responsible chemical
waste segregation and disposal.
Laboratory ventilation and environmental control systems also
play an integral role in safety protocols. These systems must be regularly inspected and maintained to
guarantee they operate effectively, ensuring airborne particles or gases from the chemical reactions are
adequately managed.
Furthermore, it is prudent for laboratory personnel working with
Cyclo(Phe-Phe) to maintain updated training on chemical hygiene and hazard communication standards. This
ongoing education may include staying current with newly identified risks, potential handling
improvements, and innovative safety solutions.
In conclusion, adopting robust safety protocols,
from personal protection to environmental controls, ensures the safe and effective handling of
Cyclo(Phe-Phe) in the laboratory. These measures safeguard personnel, prevent laboratory accidents,
preserve the integrity of experimental results, and minimize environmental impact, aligning with best
practices in laboratory safety management.
What are the environmental implications of using
Cyclo(Phe-Phe) in industrial or laboratory settings?
The utilization of Cyclo(Phe-Phe) in
industrial and laboratory environments prompts a range of environmental considerations, each of which is
essential for ensuring sustainable practices. The implications of using Cyclo(Phe-Phe) stem from its
synthesis, application, and disposal, all of which contribute to its overall environmental
footprint.
The synthesis of Cyclo(Phe-Phe) involves chemical reactions that often require organic
solvents. These solvents, if not managed correctly, can pose significant environmental risks, including
air, water, and soil contamination. Common solvents might include dimethylformamide (DMF),
dichloromethane (DCM), or acetonitrile, which have associated hazardous properties. Therefore,
minimizing solvent use through techniques like solvent recycling and employing less hazardous
alternatives is vital to reducing environmental impact.
Waste management is a critical component,
as chemical waste from Cyclo(Phe-Phe) processes needs proper categorization and disposal to prevent
environmental harm. The efficiency of waste treatment processes and the effectiveness of hazardous waste
management programs can vary significantly, impacting localized environments. Implementing green
chemistry principles, such as atom economy, sustainable resource management, and designing benign
by-products, further aids in mitigating these effects.
Industrial applications of Cyclo(Phe-Phe)
also necessitate a close look at lifecycle assessments to quantify the environmental footprint
comprehensively. This involves evaluating energy consumption, raw material usage, emissions, and waste
generated throughout its lifecycle. Strategies such as circular economy models, which emphasize waste
reduction, resource reuse, and recycling, are promising paths for minimizing environmental
impacts.
There is also a growing interest in biotechnological routes for Cyclo(Phe-Phe)
production, aiming to reduce reliance on traditional chemical synthesis methods that may involve harsh
conditions and environmentally damaging reagents. For instance, leveraging microbial fermentation or
utilizing enzymes can offer more sustainable production pathways.
Beyond the synthesis phase, the
application of Cyclo(Phe-Phe) in areas like pharmaceuticals, materials science, and food technology
calls for environmentally conscious practices. For example, in drug delivery systems, biodegradable and
biocompatible materials that minimize environmental accumulation are preferred. When used in food
sciences, ensuring the non-toxic nature and regulatory compliance of Cyclo(Phe-Phe) as a food additive
or flavor enhancer is relevant to human health and the environment.
Finally, there is an
increasing demand for comprehensive regulatory frameworks that support sustainable practices associated
with Cyclo(Phe-Phe). Regulations ensure that the transport, storage, and handling of such chemicals
align with best practices to minimize accidental releases and their ecological
consequences.
While the use of Cyclo(Phe-Phe) offers promising opportunities across various
fields, these benefits must be balanced with careful consideration of their environmental footprints.
This involves striving for advancements in greener synthesis methods, effective waste management,
lifecycle assessments, and regulatory compliance — all crucial elements in promoting the responsible and
sustainable implementation of Cyclo(Phe-Phe) in industrial and laboratory settings.
How does
Cyclo(Phe-Phe) relate to broader research in peptide science, and what future directions could the
research take?
Cyclo(Phe-Phe) lies at an exciting intersection of peptide science, serving as
both a cornerstone in understanding peptide behavior and as a springboard for future research
directions. Its cyclic structure offers a unique perspective on peptide chemistry, deviating from the
more commonly studied linear peptides and contributing to a broader understanding of the folding and
stability characteristics inherent to peptides.
Cyclic peptides like Cyclo(Phe-Phe) provide
invaluable insights into the stabilization strategies that proteins use to maintain their complex
three-dimensional structures. The robust cyclic backbone of such dipeptides is a critical study model
for elucidating interactions that sustain peptide conformation and stability. This aspect of peptide
research is fundamental to drug design, where structure-functional relationships are essential for the
development of potent, stable, and selective therapeutic agents.
Cyclo(Phe-Phe) also contributes
to advances in understanding and mitigating protein-protein interactions. These interactions underpin
many biological processes and are often implicated in diseases. By studying how Cyclo(Phe-Phe) and
similar structures modulate these interactions, researchers can develop novel inhibitors or modulators
with therapeutic potential.
In broader peptide science, understanding the self-assembly
mechanisms of Cyclo(Phe-Phe) has stimulated research into nanostructure formation. This aspect of cyclic
peptides is harnessed in designing novel nanomaterials, offering groundbreaking potential for biomedical
applications. For instance, Cyclo(Phe-Phe) derivatives are explored for their ability to form
nanostructures that enhance drug delivery mechanisms, improving drug solubility, stability, and
targeting abilities.
Future research directions evolving from Cyclo(Phe-Phe) could encompass a
range of exciting developments. One prospective area is combinatorial biosynthesis — blending chemical
and biological synthesis routes to derive new peptide sequences with cyclo-dipeptide cores. This could
enable synthetic biology applications generating libraries of novel peptides for screening as drug
candidates or material science applications.
Another promising research avenue could delve into
exploring Cyclo(Phe-Phe) analogs with modified side chains, unraveling functional diversity while
maintaining beneficial cyclic stability. Such modifications could unlock a broader scope of functional,
selective, potent compounds for medical and technological applications.
Furthermore, greener
synthetic methods for producing Cyclo(Phe-Phe) and cyclic peptides in general are desirable. Advances in
enzymatic synthesis and microbial production leverage bio-based systems to create peptides via
eco-friendly processes, minimizing harmful chemical byproducts and fostering sustainable
practices.
Finally, the integration of computational modeling techniques with Cyclo(Phe-Phe)
research offers opportunities for unprecedented insights into peptide interactions and functions.
High-throughput molecular simulations and machine learning models can predict Cyclo(Phe-Phe) behavior in
complex biological systems, accelerating the discovery of potential applications and enhancing
understanding of underlying mechanisms.
In summary, Cyclo(Phe-Phe) profoundly influences peptide
science, providing foundational insights while simultaneously fueling innovation and exploration of new
scientific horizons. Its utility spans from fundamental biochemical studies to technological
applications, offering boundless opportunities for advancing knowledge and facilitating breakthroughs
across numerous scientific domains.
Can Cyclo(Phe-Phe) be used as a therapeutic agent, and what
challenges does its use entail?
Cyclo(Phe-Phe) as a therapeutic agent is an intriguing prospect
within medicinal chemistry and drug development. Its potential applications derive from its inherent
stability, relative simplicity, and ability to modulate biological activities, making it a strong
candidate for therapeutic exploration. Nevertheless, utilizing Cyclo(Phe-Phe) as a therapeutic comes
with challenges that need careful consideration and strategic research to address.
One key
advantage of Cyclo(Phe-Phe) is its structure, which offers increased resistance to enzymatic degradation
compared to linear peptides. This characteristic makes it a promising scaffold for drug design,
particularly in scenarios where proteolytic stability is essential. The cyclic structure can better
traverse biological environments and reach therapeutic targets without premature breakdown, potentially
increasing the therapeutic efficacy and duration of action.
Moreover, Cyclo(Phe-Phe) has
demonstrated bioactivity, notably in antimicrobial settings, showing potential to evolve into a novel
class of antibiotics. With the rising threat of antimicrobial resistance, exploring Cyclo(Phe-Phe) and
its derivatives as broad-spectrum or targeted antibiotics represents a critical research avenue.
However, translating this promise into clinical applications demands comprehensive understanding of its
mechanisms, spectrum of activity, and resistance profile.
Despite these promising aspects, the
development of Cyclo(Phe-Phe) as a therapeutic agent encompasses significant challenges. One of the
primary hurdles is achieving selective and potent biological activity without off-target effects or
toxicity. Peptides often suffer from drawbacks like rapid clearance from the body and limited cellular
uptake, necessitating advances in drug formulation and delivery technologies to mitigate these
limitations.
Another challenge involves scalability and cost-effective synthesis, crucial for
large-scale pharmaceutical production. Synthesis methods must evolve to efficiently produce high-purity
Cyclo(Phe-Phe) at competitive costs while adhering to regulatory standards for pharmaceutical compounds.
Innovations such as enzyme-catalyzed synthesis or fermentation-based production could alleviate some of
these challenges, providing sustainable routes to obtaining cyclic peptides.
Pharmacokinetic and
pharmacodynamic profiling is necessary to understand Cyclo(Phe-Phe)'s behavior within biological systems
fully. These evaluations are pivotal in determining appropriate dosing regimens, identifying potential
side effects, and ensuring overall safety and efficacy. Long-term studies evaluating metabolism,
distribution, excretion, and interaction within target organisms are indispensable components in these
assessments.
Regulatory and approval processes further compound the complexity. Developing any
novel therapeutic agent, including Cyclo(Phe-Phe) derivatives, must navigate rigorous regulatory
landscapes, requiring substantial data on safety, efficacy, manufacturing practices, and quality
controls.
Finally, while Cyclo(Phe-Phe) serves as a structural template, its modification through
chemical or biological means is crucial to tailor its properties for specific therapeutic contexts.
Rational design, combinatorial synthesis, and molecular modeling are valuable tools in this endeavor,
facilitating the generation of optimized derivatives with desired biological functions.
In sum,
while Cyclo(Phe-Phe) holds marked potential as a therapeutic agent, its practical application demands
addressing multifaceted challenges involving stability, bioactivity, scalable synthesis, pharmacological
profiling, and regulatory compliance. Continued research in these areas is imperative to unlocking
Cyclo(Phe-Phe)'s full therapeutic promise and translating its benefits into tangible clinical outcomes.