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852079 Fmoc-Asp-ODmab

Overview

Replacement Information

Key Spec Table

CAS #Hill FormulaMolar Mass
172611-77-7C₃₉H₄₂N₂O₈666.77 g/mol

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      8520790005
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          Description
          Catalogue Number852079
          Replaces04-12-1176
          Brand Family Novabiochem®
          Alternate Names
          • N-α-Fmoc-L-aspartic acid α-4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]-amino} benzyl ester
          Background InformationQuasi-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".
          References
          Product Information
          CAS number172611-77-7
          Hill FormulaC₃₉H₄₂N₂O₈
          Molar Mass666.77 g/mol
          Structure formula ImageStructure formula Image
          Quality LevelMQ200
          Applications
          ApplicationFmoc-Asp-ODmab Novabiochem®. CAS 172611-77-7, molar mass 666.77 g/mol.
          Biological Information
          Physicochemical Information
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          Storage class10 - 13 Other liquids and solids
          WGKWGK 2 obviously hazardous to water
          Safety Information
          Product Usage Statements
          Storage and Shipping Information
          StorageStore at -15°C to -25°C.
          Packaging Information
          Transport Information
          Supplemental Information
          Specifications
          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
          Global Trade Item Number
          Catalogue Number GTIN
          8520790001 04027269088545
          8520790005 04027269088552

          Documentation

          Fmoc-Asp-ODmab SDS

          Title

          Safety Data Sheet (SDS) 

          Citations

          Title
          • [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, ╔ditions 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.