Fmoc-(R)-2-(7-octenyl)Ala-OH
Fmoc-(R)-2-(7-octenyl)Ala-OH (CAS: 945212-26-0) is an olefinic alpha-methyl amino acid with the molecular formula C26H31NO4 and a molecular weight of 421.53. This compound is specifically designed for peptide stapling applications. When incorporated into a peptide chain alongside a complementary molecule, it enables the formation of a stable macrocycle through ring-closing metathesis. This structural modification enhances helical stability, leading to improved proteolytic resistance and cellular uptake in resulting peptides.
- IUPAC
- (R)-N-Fmoc-α-(7-Octenyl)alanine,Fmoc-(R)-2-(7-octenyl)alanine,Fmoc-(R)-2-amino-2-methyl-dec-6-enoic acid
- Synonyms
- (R)-N-Fmoc-α-(7-Octenyl)alanine,Fmoc-(R)-2-(7-octenyl)alanine,Fmoc-(R)-2-amino-2-methyl-dec-6-enoic acid
Peptide Stapling
Fmoc-(R)-2-(7-octenyl)Ala-OH serves as a key building block for creating stapled peptides. Its olefinic side chain participates in ring-closing metathesis reactions, stabilizing the peptide's alpha-helical structure.
Chemical Biology
This amino acid derivative is utilized in chemical biology research to engineer peptides with enhanced stability and modified biological activity. The resulting stapled peptides can offer improved pharmacokinetic profiles.
Peptide Synthesis
Incorporation into solid-phase or solution-phase peptide synthesis allows for the introduction of the octenyl side chain, a precursor for subsequent macrocyclization reactions.
Chemical Synthesis
Serves as a versatile intermediate in complex organic synthesis, particularly for constructing conformationally constrained peptide analogues and peptidomimetics.
| Molecular weight | 421.53 |
|---|---|
| Empirical formula | C26H31NO4 |
| 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-(R)-2-(7-octenyl)Ala-OH used for?
+
Fmoc-(R)-2-(7-octenyl)Ala-OH is primarily used as an amino acid building block for peptide stapling, enabling the stabilization of alpha-helical structures in peptides, which can improve proteolytic stability and cellular uptake.
What are the CAS number and molecular formula for Fmoc-(R)-2-(7-octenyl)Ala-OH?
+
The CAS number for Fmoc-(R)-2-(7-octenyl)Ala-OH is 945212-26-0, and its molecular formula is C26H31NO4.
What grade and purity does Tech Serve Solutions supply?
+
Tech Serve Solutions supplies Fmoc-(R)-2-(7-octenyl)Ala-OH as a research-grade chemical. TSS does not represent this product as USP, BP, EP, or other pharmacopoeial grades.
How should Fmoc-(R)-2-(7-octenyl)Ala-OH be handled and stored?
+
Fmoc-(R)-2-(7-octenyl)Ala-OH is classified as environmentally hazardous (H400). It should be stored at -20°C and handled with care to prevent release into the environment (P273).
How is this chemical shipped and exported?
+
Fmoc-(R)-2-(7-octenyl)Ala-OH is shipped as UN 3077, Class 9, Packing Group III, suitable for international export by Tech Serve Solutions, a specialist global supplier.
How can I request a sample or quote for Fmoc-(R)-2-(7-octenyl)Ala-OH?
+
Please contact our sales department through our website or by phone to request a sample or a formal quotation for Fmoc-(R)-2-(7-octenyl)Ala-OH.
▶ Related products
1-(2-Fluorobenzyl)piperazine
C11H15FN2
Chemical Synthesis
1-(2-Fluorophenyl)biguanide hydrochloride
Chemical Synthesis
1-(2-Fluorophenyl)cyclopropanecarboxylic acid
C10H9FO2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine
C10H13FN2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine monohydrochloride
C10H13FN2 · HCl
Chemical Synthesis
1-(2-Furoyl)-1H-benzotriazole
C11H7N3O2
Chemical Synthesis
1-(2-Furoyl)piperazine
C9H12N2O2
Chemical Synthesis
1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione
Chemical Synthesis
▶ Explore more
3-Methyl-1,5-di-p-tolyl-1,4-pentazadiene
Chemical Synthesis
3-Methyl-1,5-pentanediol
Chemical Synthesis
3-Methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine
C11H13N3
Chemical Synthesis
3-Methyl-1-(3′-sulfoamidophenyl)-5-pyrazolone
C10H11N3O3S
Chemical Synthesis