8.52351

cis-Fmoc-Pro(4-N3)-OH

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

• Synonym(s): cis-Fmoc-Pro(4-N3)-OH, Fmoc-(2S, 4S)-4-azidoproline
• Empirical Formula (Hill Notation): C₂₀H₁₈N₄O₄
• CAS Number: 263847-08-1
• Molecular Weight: 378.38
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• product name: cis-Fmoc-Pro(4-N3)-OH, Novabiochem^®
• 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/C20H18N4O4/c21-23-22-12-9-18(19(25)26)24(10-12)20(27)28-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18H,9-11H2,(H,25,26)/t12-,18-/m0/s1
• InChI key: HOPXMBBEYJTPNX-SGTLLEGYSA-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
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%): ≥ 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 Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable