Fmoc-Lys(Dde)-OH

Description

• General description: Quasi-orthogonally-protected Lys derivative for Fmoc SPPS. 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 [10,11,12,13,14].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]. Associated Protocols and Technical ArticlesCleavage and Deprotection Protocols for Fmoc SPPSLiterature references[1] B. W. Bycroft, et al. (1993) J. Chem. Soc., Chem. Commun., 778. [2] B. Rohwedder, et al. (1998) Tetrahedron Lett., 39, 1175. [3] N. Ahlborg (1995) J. Immun. Meth., 179, 269. [4] B. W. Bycroft, et al. in ′Peptides, Chemistry, Structure & Biology, Proc. 13th American peptide Symposium′, R. S. Hodges & J. A. Smith (Eds), ESCOM, Leiden, 1994, pp. 727. [5] J. Mack, et al. (2001) J. Peptide Sci., 7, 338. [6] G. B. Bloomberg, et al. (1993) Tetrahedron Lett., 34, 4709. [7] P. Dumy, et al. (1995) Tetrahedron Lett., 36, 1255. [8] J. Eichler, et al. (1994) Pept. Res., 7, 300. [9] C. G. Fields, et al. (1993) Biopolymers, 33, 1695. [10] H. F. Brugghe, et al. (1994) Int. J. Peptide Protein Res., 43, 166. [11] P. Hoogerhout, et al. (1995) Infection & Immunity, 63, 3473. [12] D. Lelievre, et al. (1995) Tetrahedron Lett., 36, 9317. [13] P. Hoogerhout, et al. (1999) J. Peptide Res., 54, 436. [14] P.J. Conolly, et al. (2000) Tetrahedron Lett., 41, 5187. [15] K. Augustyns, et al. (1998) J. Peptide Res., 51, 127. [16] A. Srinivasan, et al., Poster 111 presented at the 15th American Peptide Symposium, Nashville, 1997.[17] S. Peluso, et al. (1999) J. Org. Chem., 64, 7114. [18] J. J. Diaz-Mochón, et al. (2004) Org. Lett., 6, 1127.
• Linkage: Replaces: 04-12-1121
• 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 %To see the solvent systems used for TLC of Novabiochem® products please click here.
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