Analysis Note

Colour (visual): white to slight yellow to beigeAppearance of substance (visual): powderIdentity (IR): passes testEnantiomeric 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 solubleAssay (acidimetric): ≥ 90.0 %Water (K. F.): ≤ 1.0 %For TLC-Systems see our General Catalog

General description

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 A-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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Legal Information

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Linkage

Replaces: 04-12-1121