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Fmoc-Lys(Dde)-OH

Fmoc-Lys(Dde)-OH Novabiochem®. CAS 150629-67-7, molar mass 532.63 g/mol., Novabiochem®

Synonym: N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-lysine

  • CAS Number 150629-67-7

  • Linear Formula C₃₁H₃₆N₂O₆

  • Molecular Weight 532.63 g/mol

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Properties

Related Categories Amino Acids & Derivatives, Chemical Biology, Chemical Synthesis, Lysine, Peptide Chemistry More...
brand family   Novabiochem
packaging   1 g in Glass bottle (8520570001)
  5 g in Glass bottle (8520570005)
mp   80 °C decomposes
shipped in   ambient
storage temp.   Store at -15°C to -25°C.
specifications   Colour (visual): white to slight yellow to beige
  Appearance of substance (visual): powder
  Identity (IR): passes test
  Enantiomeric purity: ≥ 99.5 % (a/a)
  Purity (TLC(157B)): ≥ 98 %
  Purity (TLC(CMA2)): ≥ 98 %
  Assay (HPLC, area%): ≥ 97.0 % (a/a)
  Solubility (1 mmole in 2 ml DMF): clearly soluble
  Assay (acidimetric): ≥ 90.0 %
  Water (K. F.): ≤ 1.0 %
  For TLC-Systems see our General Catalog

Description

Background information

Quasi-orthogonally-protected Lys derivative. The Fmoc group can be removed selectively by treatment with piperidine; the Dde group is cleaved with 2% hydrazine in DMF [1]. When removing Dde in the presence of allyl based protecting groups, allyl alcohol should be included in the deprotection solution to prevent reduction of the allyl group [2].

Lys(Dde) has been employed in the following applications: synthesis of branched peptides [1] and di-epitopic peptides [3]; preparation of MAP core molecules and lipo-MAPs [4, 5]; construction of cyclic peptides [6], TASP molecules [7], templates for combinatorial chemistry [8] and synthetic proteins [9]; preparation of peptides modified at the lysine side-chain [10-14].

It has been reported that Dde can migrate from the side-chain of Lys to the unprotected side-chain of another Lys residue [15], and from the β-amino group to the α-amino group of Dpr [16]. In the former instance, this problem can be overcome by using Fmoc-Lys(ivDde)-OH (852082) or using DBU/DMF (2:98) for Fmoc group removal [15, 17].

Full orthogonality of Dde with Fmoc has recently been demonstrated when hydroxylamine is used for Dde removal [18].

The product number for this product was previously 04-12-1121.

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Safety Information

HS Code 
2924 29 70
Storage class 
10 - 13 Other liquids and solids
WGK 
WGK 2 water endangering
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