Description

• General description: Orthogonally-protected building block for the synthesis of head-to-tail cyclic peptides [1,2,3,4,5] by Fmoc SPPS. The α-allyl ester can be selectively removed in the presence of Fmoc- and tBu-based protecting groups by treatment with Pd(Ph3P)4/ CHCl3/AcOH/NMM [6], thereby facilitating the synthesis of branched esters, amides, lactones and lactams incorporating an aspartyl unit. Associated Protocols and Technical ArticlesCleavage and Deprotection Protocols for Fmoc SPPSLiterature references[1] W. Bannwarth, et al. (1992) Tetrahedron Lett., 33, 4557. [2] F. Albericio, et al. (1993) Tetrahedron Lett., 34, 1549. [3] J. Eichler, et al. (1994) Pept. Res., 7, 300. [4] J. Eichler, et al. in ′Peptides 1994, Proc. 23rd European Peptide Symposium′, H. Maia (Eds), ESCOM, Leiden, 1994, pp. 461. [5] J. Eichler, et al. in ′Solid Phase Synthesis & Combinatorial Libraries, 4th International Symposium′, R. Epton (Eds), Mayflower Scientific Ltd., Birmingham, 1996, pp. 201. [6] S. A. Kates, et al. in ′Peptides, Chemistry, Structure & Biology, Proc. 13th American Peptide Symposium′, ESCOM, Leiden, 1994, pp. 113.
• Linkage: Replaces: 04-12-1157
• Analysis Note: Color (visual): white to slight yellow to beigeAppearance of substance (visual): powderIdentity (IR): conformsEnantiomeric purity: ≥ 99.0 % (a/a)Purity (TLC(CMA2)): ≥ 98 %Purity (TLC(157A)): ≥ 98 %Assay (HPLC, area%): ≥ 98.0 % (a/a)Solubility (1 mmole in 2 ml DMF): clearly solubleAssay (acidimetric): ≥ 97.0 %Water (K. F.): ≤ 1.5 %To see the solvent systems used for TLC of Novabiochem® products please click here.
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany