F6562

Fmoc-(R)-2-(7-octenyl)Ala-OH

for peptide synthesis

• Synonym(s): (R)-N-Fmoc-α-(7-Octenyl)alanine, Fmoc-(R)-2-(7-octenyl)alanine, Fmoc-(R)-2-amino-2-methyl-dec-6-enoic acid
• Empirical Formula (Hill Notation): C₂₆H₃₁NO₄
• CAS Number: 945212-26-0
• Molecular Weight: 421.53
• MDL number: MFCD12925761
• UNSPSC Code: 12352209
• PubChem Substance ID: 329799756
• NACRES: NA.26

Properties

• product name: Fmoc-(R)-2-(7-octenyl)Ala-OH,
• form: solid
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• application(s): peptide synthesis
• functional group: Fmoc
• storage temp.: −20°C
• SMILES string: O=C(OCC1C(C=CC=C2)=C2C3=C1C=CC=C3)N[C@@](CCCCCCC=C)(C)C(O)=O
• InChI: 1S/C26H31NO4/c1-3-4-5-6-7-12-17-26(2,24(28)29)27-25(30)31-18-23-21-15-10-8-13-19(21)20-14-9-11-16-22(20)23/h3,8-11,13-16,23H,1,4-7,12,17-18H2,2H3,(H,27,30)(H,28,29)/t26-/m1/s1
• InChI key: MADFVGMQNXRFAF-AREMUKBSSA-N

Description

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.

Safety Information

• Pictograms: GHS09
• Signal Word: Warning
• Hazard Statements: H400
• Precautionary Statements: P273 - P391 - P501
• Hazard Classifications: Aquatic Acute 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable