8.52072

Fmoc-Asp-OAll

Novabiochem^®

• Synonym(s): Fmoc-Asp-OAll, N-α-Fmoc-L-aspartic acid α-allyl ester
• Empirical Formula (Hill Notation): C₂₂H₂₁NO₆
• CAS Number: 144120-53-6
• Molecular Weight: 395.41
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD00467715

Properties

• Quality Level: 200
• product line: Novabiochem^®
• assay: ≥97.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• mp: 95 °C (decomposes)
• application(s): peptide synthesis
• functional group: carboxylic acid
• storage temp.: 2-30°C
• SMILES string: N([C@@H](CC(=O)O)C(=O)OCC=C)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C22H21NO6/c1-2-11-28-21(26)19(12-20(24)25)23-22(27)29-13-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h2-10,18-19H,1,11-13H2,(H,23,27)(H,24,25)/t19-/m0/s1
• InChI key: ZJMVIWUCCRKNHY-IBGZPJMESA-N

Description

General description

Orthogonally-protected building block for the synthesis of head-to-tail cyclic peptides ^[1,2,3,4,5] by Fmoc SPPS. The α-allyl ester can be selectively removed in the presence of Fmoc- and tBu-based protecting groups by treatment with Pd(Ph₃P)₄/ CHCl₃/AcOH/NMM ^[6], thereby facilitating the synthesis of branched esters, amides, lactones and lactams incorporating an aspartyl unit.

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

Literature references

^[1] W. Bannwarth, et al. (1992) Tetrahedron Lett., 33, 4557.
^[2] F. Albericio, et al. (1993) Tetrahedron Lett., 34, 1549.
^[3] J. Eichler, et al. (1994) Pept. Res., 7, 300.
^[4] J. Eichler, et al. in ′Peptides 1994, Proc. 23rd European Peptide Symposium′, H. Maia (Eds), ESCOM, Leiden, 1994, pp. 461.
^[5] J. Eichler, et al. in ′Solid Phase Synthesis & Combinatorial Libraries, 4th International Symposium′, R. Epton (Eds), Mayflower Scientific Ltd., Birmingham, 1996, pp. 201.
^[6] S. A. Kates, et al. in ′Peptides, Chemistry, Structure & Biology, Proc. 13th American Peptide Symposium′, ESCOM, Leiden, 1994, pp. 113.

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): conforms
Enantiomeric purity: ≥ 99.0 % (a/a)
Purity (TLC(CMA2)): ≥ 98 %
Purity (TLC(157A)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 97.0 %
Water (K. F.): ≤ 1.5 %

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

Other Notes

Replaces: 04-12-1157

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable