Synonym |
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH |
Species |
Not specified |
Protein Accession |
Not specified |
Purity |
Greater than 95% as determined by HPLC |
Endotoxin Level |
Less than 1 EU/μg |
Biological Activity |
Not specified |
Expression System |
Not specified |
Fusion Tag |
Not specified |
Predicted Molecular Mass |
Not specified |
Formulation |
Lyophilized from a 0.22 μm filtered solution of PBS |
Reconstitution |
Centrifuge the vial prior to opening. Reconstitute in water to a concentration of 0.1-1.0 mg/ml.
|
Storage & Stability |
Store at -20°C. For extended storage, store at -20°C or -80°C. |
FAQ
What is H-Ala-D-Glu(K-D-Ala-D-Ala)-OH and what are its primary applications?
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH is a synthetic peptide consisting of a particular amino acid sequence
that imparts unique biochemical properties relevant for research in biological and medicinal chemistry.
This peptide is composed of alanine, glutamic acid, and lysine, among others, forming a structured
compound that plays a role in various research domains. Its intriguing structure makes it particularly
valuable for studies investigating enzymatic activity, protein interactions, or cellular processes where
D-amino acids are involved. This peptide is, notably, of interest in the field of antimicrobial
research. Its sequence mimics certain elements found in peptidoglycan structures, making it a useful
tool in studying the mechanism of action of antibiotics, particularly those targeting cell wall
synthesis, like vancomycin. Understanding these interactions can aid in the design of next-generation
antibiotics to combat resistant strains of bacteria.
Another application of
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH is in the development of innovative materials mimicking biological
properties for use in tissue engineering and regenerative medicine. The interplay of D-amino acids in
its sequence can influence peptide stability and resistance to proteolytic degradation, which are
desired properties in designing scaffolds for tissue growth. Combining these characteristics with
suitable polymers can tailor biomaterials for specific therapeutic requirements. Researchers are
extensively exploring how such peptides can enhance the biocompatibility and mechanical integrity of
these materials.
In a biotechnological context, this peptide can also serve as a calibration
standard for analytical techniques, such as mass spectrometry or HPLC, when analyzing complex peptide
mixtures. Its defined structure allows for precise evaluation of analytical performance, thereby
ensuring the reliability of these techniques when applied to biological samples.
In the realm of
fundamental science, H-Ala-D-Glu(K-D-Ala-D-Ala)-OH is utilized to examine stereoisomeric influences on
biological systems. Studying its interaction with enzymes that exhibit stereospecificity sheds light on
the role of chirality in metabolic pathways and the evolution of protein functions. This has profound
implications for the development of novel pharmaceuticals, as it enables the design of compounds with
high specificity and reduced side effects.
What advantages does the use of
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH offer for research compared to other peptides?
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH offers several distinctive advantages for research, largely derived
from its unique sequence containing D-amino acids. One of its primary benefits is enhanced stability.
Peptides with D-amino acids demonstrate increased resistance to enzymatic degradation, which is a
significant limitation when using peptides composed solely of L-amino acids in biological studies. This
increased stability allows researchers to conduct longer-term studies without the rapid degradation that
could compromise the integrity of experiments or the interpretation of results. The incorporation of
D-amino acids also affects the peptide's interaction with biological systems, often leading to a
reduction in immunogenicity, which is particularly advantageous in in vivo studies.
Another
advantage is this peptide's ability to serve as a mimic or analogue of bacterial cell wall structures,
particularly the D-Ala-D-Ala sequence which is critical for the action of antibiotics like vancomycin.
This mimicry allows for detailed studies into the mechanisms by which antibiotics function and,
consequently, the ways bacteria develop resistance. By providing a chemical model similar to bacterial
cell wall components, it facilitates the identification of new therapeutic targets and the development
of antibiotics with mechanisms less likely to be bypassed by resistance.
Moreover, the peptide's
broad applicability across various contexts, from fundamental biochemical research to practical
applications in drug development and materials science, underscores its utility. Its defined and stable
structure makes it an ideal candidate for standardizing assays and calibrating instruments in analytical
chemistry. It inherently fosters collaborative research efforts among chemists, biologists, and
materials scientists, as its applications cut across disciplinary
boundaries.
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH also provides valuable insights into the roles of
peptide stereochemistry in biological activity. Stereospecific interactions are fundamental to many
biochemical processes, and understanding them can drive the design of stereo-selective drugs with
enhanced efficacy. Furthermore, this peptide can serve as a scaffold for creating libraries of compounds
with potential therapeutic applications, offering a more efficient pathway in drug discovery
processes.
Lastly, the structural motifs present in H-Ala-D-Glu(K-D-Ala-D-Ala)-OH, such as those
linking side chains and the presence of reactive groups, allow it to be modified for conjugation with
targeting moieties, fluorophores, or other functional groups. This versatility enhances its potential as
a research tool, enabling experiments that probe the dynamics of biological systems in ways that were
previously not feasible.
How can H-Ala-D-Glu(K-D-Ala-D-Ala)-OH be used to study antibiotic
resistance mechanisms?
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH serves as a powerful tool in studying
antibiotic resistance mechanisms due to its structural resemblance to components of bacterial cell
walls, particularly the terminal D-alanyl-D-alanine moiety which is the target of many antibiotics,
including the glycopeptide antibiotic vancomycin. Antibiotic resistance, especially among Gram-positive
bacteria, often involves modifications of the target sites that these antibiotics bind to, reducing
their efficacy. The peptide's mimicry of these specific cell wall components allows researchers to delve
into the molecular interactions that occur during antibiotic action and bacterial defense.
Using
this peptide in laboratory experiments, scientists can simulate the interactions between antibiotics and
bacterial cell walls. This simulation is crucial for understanding how antibiotics like vancomycin bind
to their bacterial targets and the subsequent steps leading to bacterial inhibition or death. By
observing these interactions in a controlled environment, researchers can pinpoint precisely how certain
bacteria modify their cell walls to evade antibiotic effects. For example, in vancomycin-resistant
strains, bacteria often alter the D-Ala-D-Ala terminus to D-Ala-D-Lactate or D-Ala-D-Serine, thereby
reducing drug binding affinity. Using H-Ala-D-Glu(K-D-Ala-D-Ala)-OH as a model, researchers can study
these modifications and develop assays to detect resistance mechanisms or even preempt their emergence
by designing inhibitors that block these resistance pathways.
Furthermore, this peptide aids in
the screening of libraries of antibiotic candidates, serving as a benchmark for evaluating which
compounds exhibit better binding affinity or resistance-breaking potential. It acts as a surrogate in
high-throughput screening assays, where binding interactions can be monitored using biophysical
techniques such as surface plasmon resonance or isothermal titration calorimetry, giving insights into
the kinetics and thermodynamics of antibiotic binding.
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH also
supports structural biology efforts. By crystallizing this peptide with antibiotic compounds,
researchers can capture high-resolution three-dimensional structures of peptide-drug complexes. Such
structural data provide a blueprint for designing new drugs that can better overcome resistance by
targeting altered bacterial peptides or new sites altogether.
The study of gene expression
changes in bacteria exposed to the peptide can also provide insights into resistance mechanisms. By
employing transcriptomic and proteomic approaches, researchers can identify key genes and proteins that
are upregulated during exposure, offering additional targets for new antibiotics or adjunct therapies
that restore antibiotic sensitivity.
In summary, H-Ala-D-Glu(K-D-Ala-D-Ala)-OH offers a
multifaceted approach to unraveling antibiotic resistance, functioning as a model compound in
structure-function studies, a benchmark in drug design assays, and a critical tool in biochemical and
genetic investigations of bacterial defense strategies.
How does H-Ala-D-Glu(K-D-Ala-D-Ala)-OH
contribute to the field of drug discovery and design?
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH plays a pivotal
role in drug discovery and design, particularly as a scaffold for developing novel therapeutic agents
aimed at combating bacterial infections and other medical challenges. The unique sequence and structural
features of this peptide make it an invaluable asset in the early stages of drug development, offering a
model system for testing hypotheses and refining drug candidates. Its use spans various phases of the
drug discovery pipeline, from target identification and validation to the optimization of lead
compounds.
In the realm of antimicrobial drug discovery, H-Ala-D-Glu(K-D-Ala-D-Ala)-OH serves as
a critical reference point for studying bacterial cell wall synthesis. By mimicking key components of
bacterial peptidoglycan, it allows researchers to explore the interruption mechanisms of antibiotics
like vancomycin, which target these structures. Understanding how existing drugs interact with such
peptide models helps in identifying vulnerabilities in bacterial defenses and guides the rational design
of new molecules with improved binding characteristics or resistance-breaking capabilities.
This
peptide also aids in the high-throughput screening processes essential for drug discovery. It can be
employed in assays that rapidly assess the binding affinity and specificity of large libraries of
compounds, facilitating the identification of promising candidates that can be further developed into
therapeutics. The results garnered from these screenings are crucial for narrowing down potential drug
leads and optimizing them through medicinal chemistry efforts.
Furthermore,
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH can be utilized as a tool to study structure-activity relationships (SAR).
By systematically varying the peptide’s sequence or functional groups, researchers can derive insights
into how specific modifications affect biological activity or interactions with drug targets. These
insights are invaluable for the rational design of compounds with desired pharmacological profiles,
enhancing effectiveness, and reducing unwanted side effects.
In the context of protein-protein
interactions and allosteric modulation, this peptide offers a template for designing small molecules or
peptidomimetics that can modulate these complex interactions. Such molecules have significant
therapeutic potential as they can either inhibit undesired protein interactions or stabilize favorable
ones, providing novel approaches to treating diseases that traditional small-molecule drugs cannot
address.
Moreover, due to its stability against proteolytic degradation attributed to the
presence of D-amino acids, H-Ala-D-Glu(K-D-Ala-D-Ala)-OH is explored for applications beyond
antimicrobials, such as drug delivery systems. Its robustness makes it suitable for conjugation with
other therapeutic agents, enhancing their delivery and efficacy. Researchers are particularly interested
in its potential as a carrier for delivering cytotoxic agents to cancer cells or as a targeting moiety
in bioactive conjugates.
In conclusion, H-Ala-D-Glu(K-D-Ala-D-Ala)-OH significantly enhances the
drug discovery and design process by providing a versatile scaffold for developing novel therapeutics,
tools for understanding drug-target interactions, and platforms for innovative therapeutic strategies.
Its contributions have the potential to lead to breakthroughs that address pressing medical needs and
significantly impact healthcare outcomes.
How can H-Ala-D-Glu(K-D-Ala-D-Ala)-OH be integrated
into educational settings as a learning tool?
Integrating H-Ala-D-Glu(K-D-Ala-D-Ala)-OH into
educational settings offers a dynamic way to enhance learning experiences for students studying various
fields within biology, chemistry, and pharmaceutical sciences. Given its unique properties and relevance
in cutting-edge research, this peptide can serve as a practical example to illustrate complex scientific
concepts, promote critical thinking, and encourage experimental exploration among students.
In
biochemistry and molecular biology courses, this peptide can be used to demonstrate fundamental
principles of peptide chemistry, including amino acid composition, peptide bond formation, and
stereochemistry. Students can explore how the peptide’s D-amino acids influence its properties compared
to L-amino acid peptides, providing a concrete example of the importance of stereochemistry in
biological systems. This can be supplemented with laboratory sessions where students can synthesize and
analyze peptides, enhancing their understanding of laboratory techniques such as peptide synthesis,
purification, and characterization.
For microbiology and pharmacology courses,
H-Ala-D-Glu(K-D-Ala-D-Ala)-OH can illustrate the mechanisms of antibiotic action and resistance.
Lectures can cover how this peptide mimics bacterial cell wall components targeted by antibiotics,
helping students grasp the concept of antibiotic binding and the biochemical basis of resistance. Case
studies and discussion sessions can be incorporated to examine real-world challenges, such as the rise
of antibiotic-resistant strains and strategies sought in research to address these issues, fostering
problem-solving skills and awareness of current scientific endeavors.
In analytical chemistry
classes, the peptide presents an opportunity to teach students about various analytical methods. It can
be used as a standard in exercises involving techniques like mass spectrometry, high-performance liquid
chromatography (HPLC), and nuclear magnetic resonance (NMR) spectroscopy. Through hands-on
experimentation, students learn how to analyze and interpret data, gaining proficiency in instruments
and methods crucial for peptide analysis.
Furthermore, H-Ala-D-Glu(K-D-Ala-D-Ala)-OH can play a
role in interdisciplinary projects or capstone courses where students are tasked with designing a
research project or a new drug. By integrating knowledge from organic chemistry, biochemistry, and
pharmacology, students can propose studies involving this peptide, developing a strategic approach to
investigating its properties or potential applications. Such projects encourage collaboration, synthesis
of diverse knowledge areas, and application of theoretical concepts to practical problems.
In
advanced graduate seminars, the peptide can serve as a subject for discussions on contemporary research
trends. Students can be assigned to review literature or conduct meta-analyses on studies involving this
peptide, leading seminars on its various applications and implications in fields like antimicrobial
research, drug development, or bioengineering. This deep dive helps students develop literature
research, data analysis, and public speaking skills, preparing them for future academic and professional
pursuits.
Lastly, providing access to materials such as H-Ala-D-Glu(K-D-Ala-D-Ala)-OH in
educational settings underscores the importance of research-informed teaching, where students learn not
only through textbooks but through direct engagement with materials used in professional research labs.
This approach can significantly capstone the educational experience by demystifying the transition from
learning theoretical content to applying it in real-world scientific contexts.