8.52326

Fmoc-azidolysine

≥98.0% (HPLC), for peptide synthesis, Novabiochem^®

• Sinónimos: Fmoc-azidolysine
• Fórmula empírica (notación de Hill): C₂₁H₂₂N₄O₄
• Número de CAS: 159610-89-6
• Peso molecular: 394.42
• Número MDL: MFCD13182319
• Código UNSPSC: 12352209
• NACRES: NA.22

Propiedades

• Nombre del producto: Fmoc-azidolysine, Novabiochem^®
• Nivel de calidad: 200
• Línea del producto: Novabiochem^®
• Ensayo: ≥98.0% (HPLC)
• Formulario: powder
• idoneidad de la reacción: reaction type: Fmoc solid-phase peptide synthesis
• fabricante / nombre comercial: Novabiochem^®
• aplicaciones: peptide synthesis
• grupo funcional: azide
• temp. de almacenamiento: 15-25°C
• cadena SMILES: [N+](=[N-])=NCCCC[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O
• InChI: 1S/C21H22N4O4/c22-25-23-12-6-5-11-19(20(26)27)24-21(28)29-13-18-16-9-3-1-7-14(16)15-8-2-4-10-17(15)18/h1-4,7-10,18-19H,5-6,11-13H2,(H,24,28)(H,26,27)/t19-/m0/s1
• Clave InChI: PJRFTUILPGJJIO-IBGZPJMESA-N

Descripción

Descripción general

A useful tool for the synthesis of branched, side-chain modified and 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.

Aplicación

Recent applications of Fmoc-azidolysine include:

• In the synthesis of a cationic cell-penetrating peptide (CPP) by click-chemistry.[4]
• In the preparation of a peptide-resorcinarene conjugate by click chemistry.[5]

Nota de análisis

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Información legal

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

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 1
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable