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 Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Literature 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 beige
Appearance of substance (visual): powder
Identity (IR): conforms
Enantiomeric 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 soluble
Assay (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
- UPC:
- 41115717
- Condition:
- New
- Weight:
- 1.00 Ounces
- HazmatClass:
- No
- WeightUOM:
- LB
- MPN:
- 8520720001