8.52079

Fmoc-Asp-ODmab

Novabiochem^®

• Sinónimos: Fmoc-Asp-ODmab, N-α-Fmoc-L-aspartic acid α-4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]-amino} benzyl ester
• Fórmula empírica (notación de Hill): C₃₉H₄₂N₂O₈
• Número de CAS: 172611-77-7
• Peso molecular: 666.76
• Número MDL: MFCD00797876
• Código UNSPSC: 12352209
• NACRES: NA.22

Propiedades

• Nivel de calidad: 200
• Línea del producto: Novabiochem^®
• Ensayo: ≥95.0% (HPLC); ≥97% (TLC)
• Formulario: powder
• idoneidad de la reacción: reaction type: Fmoc solid-phase peptide synthesis
• fabricante / nombre comercial: Novabiochem^®
• aplicaciones: peptide synthesis
• grupo funcional: carboxylic acid
• temp. de almacenamiento: 15-25°C
• cadena SMILES: N([C@@H](CC(=O)O)C(=O)OCc4ccc(cc4)NC(=C5C(=O)CC(CC5=O)(C)C)CC(C)C)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C39H42N2O8/c1-23(2)17-31(36-33(42)19-39(3,4)20-34(36)43)40-25-15-13-24(14-16-25)21-48-37(46)32(18-35(44)45)41-38(47)49-22-30-28-11-7-5-9-26(28)27-10-6-8-12-29(27)30/h5-16,23,30,32,40H,17-22H2,1-4H3,(H,41,47)(H,44,45)/t32-/m0/s1
• Clave InChI: QPTKEHUFSCXXEH-YTTGMZPUSA-N

Descripción

Descripción general

Quasi-orthogonally-protected Asp derivative.The Dmab group can be removed selectively in the presence of tBu-based protecting groups by treatment with 2% hydrazine in DMF ^[1], making this derivative an extremely useful tool for the preparation of cyclic peptides by Fmoc SPPS or for library synthesis. Occasionally sluggish cleavage of the aminobenzyl moiety is observed ^[2,3]. In these instances, washing the support with 20% DIPEA in DMF/water (9:1) ^[2] or HCl in dioxane ^[4] has been found to be efficacious. For the on-resin synthesis of side-chain to side-chain lactam bridged peptides, the combination of Lys(ivDde) and Asp(ODmab) is particularly advantageous since both side-chains can be simultaneously unmasked in a single step.To avoid aspartimide formation, it is advisable to employ an Hmb- or Dmb-protected derivative for introduction of the preceding residue.For applications of this derivative in the synthesis of cyclic peptides, see references ^{[5 - 7]}.

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

Literature references

^[1] W. C. Chan, et al. (1995) J. Chem. Soc., Chem. Commun., 2209.
^[2] S. Künzel, et al. Poster 17 presented at Solid Phase Synthesis & Combinatorial Libraries, Southampton, September 2001.
^[3] K. F. Medzihradszky, et al. (2002) Lett. Pept. Sci., 8, 1.
^[4] Albericio, et al.Poster 44 presented at American Peptide Symposium, San Diego 2005..
^[5] M. Cudic, et al. in ′Peptides 2000, Proc. 26th European Peptide Symposium′, J. Martinez & J.-A. Fehrentz (Eds), Paris, Editions EDK, 2001, pp. 203.
^[6] M. Cudic, et al. (2000) Tetrahedron Lett., 41, 4527.
^[7] J. P. Malkinson, et al. (2003) Org. Lett., 5, 5051.

Ligadura / enlace

Replaces: 04-12-1176

Nota de análisis

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(157A)): ≥ 97 %
Purity (TLC(CMA2)): ≥ 97 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Water (K. F.): ≤ 1.0 %

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

Información legal

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

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 2
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable