Sigma-Aldrich Fmoc-Asp-Odmab Novabiochem

Quality Level

200

Product Line

Novabiochem^®

Assay

≥95.0% (HPLC)
≥97% (TLC)

Form

powder

Reaction Suitability

reaction type: Fmoc solid-phase peptide synthesis

Manufacturer/Tradename

Novabiochem^®

Application(S)

peptide synthesis

Functional Group

carboxylic acid

Storage Temp.

15-25°C

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General Description

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 , 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) or HCl in dioxane 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

W. C. Chan, et al. (1995)J. Chem. Soc., Chem. Commun., 2209.
S. Künzel, et al. Poster 17 presented at Solid Phase Synthesis & Combinatorial Libraries, Southampton, September 2001.
K. F. Medzihradszky, et al. (2002)Lett. Pept. Sci.,8, 1.
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.

Linkage

Replaces: 04-12-1176

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