Sigma-Aldrich Fmoc-Lys(N3)-Oh 1 g

Quality Level

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

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

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

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 thiolsor 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:
M. Meldal, et Al. (1997)Tetrahedron Lett.,38, 2531.
J. T. Lundquist & J. C. Pelletier (2001)Org. Lett.,3, 781.
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.[5]

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