8.52321

Fmoc-γ-azidohomoalanine

Novabiochem^®

• Synonym(s): Fmoc-γ-azidohomoalanine
• Empirical Formula (Hill Notation): C₁₉H₁₈N₄O₄
• CAS Number: 942518-20-9
• Molecular Weight: 366.37
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Quality Level: 200
• product line: Novabiochem^®
• form: solid
• 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/C19H18N4O4/c20-23-21-10-9-17(18(24)25)22-19(26)27-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11H2,(H,22,26)(H,24,25)/t17-/m0/s1
• InChI key: CLEZARXVEABQBI-KRWDZBQOSA-N

Description

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.

Legal Information

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable