8.52326

Fmoc-azidolysine

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

• Synonym(s): Fmoc-azidolysine
• Empirical Formula (Hill Notation): C₂₁H₂₂N₄O₄
• CAS Number: 159610-89-6
• Molecular Weight: 394.42
• MDL number: MFCD13182319
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Product Name: Fmoc-azidolysine, Novabiochem^®
• Quality Segment: 200
• product line: Novabiochem^®
• assay: ≥98.0% (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-])=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
• InChI key: PJRFTUILPGJJIO-IBGZPJMESA-N

Description

General description

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 or phosphines. ^,

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.

Application

Recent applications of Fmoc-azidolysine include:

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

Analysis Note

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

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable