FMOC-LYS(DDE)-OH 5 G

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 Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature 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 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 %

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