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8.52079

Sigma-Aldrich

Fmoc-Asp-ODmab

Novabiochem®

Synonym(s):
Fmoc-Asp-ODmab, N-α-Fmoc-L-aspartic acid α-4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]-amino} benzyl ester
Empirical Formula (Hill Notation):
C39H42N2O8
CAS Number:
Molecular Weight:
666.76

Quality Level

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

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 [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].

The product number for this product was previously 04-12-1176.

To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

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 %
For TLC-Systems see our General Catalog

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Quality

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