8.52088

Fmoc-Orn(ivDde)-OH

Novabiochem^®

• Synonym(s): Fmoc-Orn(ivDde)-OH, N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-ornithine
• Empirical Formula (Hill Notation): C₃₃H₄₀N₂O₆
• CAS Number: 1198321-33-3
• Molecular Weight: 560.68
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Quality Level: 200
• product line: Novabiochem^®
• Assay: ≥85.0% (acidimetric); ≥98% (TLC); ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: amine
• storage temp.: 15-25°C
• InChI: 1S/C33H40N2O6/c1-20(2)16-27(30-28(36)17-33(3,4)18-29(30)37)34-15-9-14-26(31(38)39)35-32(40)41-19-25-23-12-7-5-10-21(23)22-11-6-8-13-24(22)25/h5-8,10-13,20,25-26,34H,9,14-19H2,1-4H3,(H,35,40)(H,38,39)/t26-/m0/s1
• InChI key: XSDVRBYPXOEYHM-SANMLTNESA-N

Description

General description

This orthogonally-protected ornithine derivative is based on the hindered Dde variant ivDde. The side-chain ivDde group is considerably more stable to piperidine than Dde and is less prone to migrate from protected to unprotected side-chains ^[1]. When removing ivDde in the presence of allyl-based protecting groups, allyl alcohol should be included in the deprotection solution to prevent reduction of the allyl group ^[2].See references ^[3,4] for applications.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] S. R. Chhabra, et al. (1998) Tetrahedron Lett., 39, 1603.
^[2] B. Rohwedder, et al. (1998) Tetrahedron Lett., 39, 1175.
^[3] V. Wittmann & S. Seeberger (2000) Angew. Chem. Int. Ed. Engl., 39, 4348.
[4] S. M. Dankwardt, et al. (2001) Bioorg. Med. Chem. Lett., 11, 2085.

Linkage

Replaces: 04-12-1203

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.0 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 85.0 %
Water (K. F.): ≤ 1.50 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

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