8.52322

Fmoc-δ-azidonorvaline

Novabiochem^®

• Synonym(e): Fmoc-δ-azidonorvaline
• Empirische Formel (Hill-System): C₂₀H₂₀N₄O₄
• CAS-Nummer: 1097192-04-5
• Molekulargewicht: 380.40
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD11052921

Eigenschaften

• Quality Segment: 200
• product line: Novabiochem^®
• assay: ≥95.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: azide
• storage temp.: 15-25°C
• SMILES string: [N+](=[N-])=NCCC[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O
• InChI: 1S/C20H20N4O4/c21-24-22-11-5-10-18(19(25)26)23-20(27)28-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,23,27)(H,25,26)/t18-/m0/s1
• InChI key: TVPIDQLSARDIPX-SFHVURJKSA-N

Beschreibung

General description

A useful tool for the synthesis of branched, side-chain modified, cyclic peptides and peptide tools for click chemistry by Fmoc SPPS. The side-chain azido group is completely stable to piperidine and TFA, but can be readily converted to an amine on the solid phase or in solution by reduction with thiols ^[1] or phosphines ^[2,3].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Guide to Selection of Orthogonally-Protected Building Blocks for Fmoc SPPS

Literature references

^[1] M. Meldal, et al. (1997) Tetrahedron Lett., 38, 2531.
^[2] J. T. Lundquist & J. C. Pelletier (2001) Org. Lett., 3, 781.
^[3] N. Nepomniaschiy, et al. (2008) Org. Lett., 10, 5243.

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable