Fmoc-(S)-2-(2-propenyl)Ala-OH
Fmoc-(S)-2-(2-propenyl)Ala-OH (CAS 288617-71-0), with the molecular formula C21H21NO4 and a molecular weight of 351.40, is a specialised unnatural amino acid. It features an olefinic side chain designed for peptide stapling applications. This compound is integral in chemical biology and peptide synthesis, facilitating the creation of stable alpha-helical structures in peptides through ring-closing metathesis.
- IUPAC
- (S)-N-Fmoc-α-2-n-propenylalanine,Fmoc-(S)-2-(2-propenyl)alanine,Fmoc-(S)-2-amino-2-methyl-4-pentenoic acid
- Synonyms
- (S)-N-Fmoc-α-2-n-propenylalanineFmoc-(S)-2-amino-2-methyl-4-pentenoic acid
Peptide Stapling
This Fmoc-protected amino acid serves as a key building block for creating stapled peptides. The olefinic side chain allows for ring-closing metathesis reactions, enabling the stabilization of peptide secondary structures like alpha-helices.
Chemical Biology Research
Used in the development of peptides with enhanced proteolytic stability and improved cellular uptake. These properties make stapled peptides valuable tools for studying biological processes and developing therapeutic agents.
Medicinal Chemistry
The alpha-helical structure stabilisation conferred by peptide stapling can lead to increased bioavailability and efficacy of peptide-based drugs, making this amino acid a critical component in drug discovery.
Chemical Synthesis
Its unique structure facilitates advanced synthetic routes in organic and peptide chemistry, allowing for precise modifications and the creation of complex peptide architectures.
| Molecular weight | 351.40 |
|---|---|
| Empirical formula | C21H21NO4 |
| Storage temperature | −20°C |
| Application | Olefinic alpha-methyl amino acid for peptide stapling. Upon incorporation of this amino acid into a peptide, along with another of the same or derivative with a different length of the olefinic side chain, the two can be ′stapled′ via a ring closing metathesis reaction with Grubb′s catalyst (product # 579726). The resulting stapled peptide macrocycle has been shown to stabilize the alpha-helical structure of peptides, which can lead to favorable biological characteristics such as increased proteolytic stability and cellular uptake. |
Hazard statements
- H400Very toxic to aquatic life
Precautionary statements
- P273Avoid release to the environment
| Transport (UN / ADR) | UN 3077 9 / PGIII |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | N |
| Risk statements (R) | 50 |
| Safety statements (S) | 61 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Fmoc-(S)-2-(2-propenyl)Ala-OH used for?
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Fmoc-(S)-2-(2-propenyl)Ala-OH is used for peptide stapling, enabling the stabilization of alpha-helical structures in peptides. This leads to enhanced proteolytic stability and cellular uptake, making it valuable in chemical biology and medicinal chemistry research.
What are the CAS number and formula for Fmoc-(S)-2-(2-propenyl)Ala-OH?
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The CAS number is 288617-71-0 and the empirical formula (Hill notation) is C21H21NO4.
What grade and purity does Tech Serve Solutions supply for Fmoc-(S)-2-(2-propenyl)Ala-OH?
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Tech Serve Solutions supplies this chemical for research purposes. Specific purity and assay details are available upon request or on the product's Certificate of Analysis. It is not supplied as USP, BP, EP, or pharmaceutical grade.
How should Fmoc-(S)-2-(2-propenyl)Ala-OH be handled and stored?
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Fmoc-(S)-2-(2-propenyl)Ala-OH is classified as hazardous to the aquatic environment (H400). It should be handled with appropriate personal protective equipment and stored at -20°C as per safety guidelines to maintain its integrity.
Is Fmoc-(S)-2-(2-propenyl)Ala-OH suitable for export?
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Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals. We can facilitate the export of Fmoc-(S)-2-(2-propenyl)Ala-OH, adhering to all relevant shipping regulations (e.g., UN 3077 9 / PGIII).
How can I request a sample or quote for Fmoc-(S)-2-(2-propenyl)Ala-OH?
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To request a sample or quote, please contact our sales team through the 'Contact Us' section of our website or via the direct inquiry form on the product page.
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