Fmoc-(FmocHmb)Gly-OH

Description

• General description: Hmb protection of amide bonds has been shown to inhibit aggregation of "difficult" peptides by Fmoc SPPS, thereby leading to products of increased purity [1,2,3,4,5,6]. Retention of Hmb groups on the cleaved peptide can greatly improve the solubility of protected peptide fragments [7, 8] and otherwise intractable sequences [9,10,11]. Furthermore, using a Hmb-protected derivative for incorporation of the residue linked to the carboxyl group of Asp or Asn residues has been found to suppress formation of aspartimide and piperidide related by-products [12,13,14]. For a comparison of the efficiency of Hmb and pseudoprolines in preventing aggregation, see [15]. Associated Protocols and Technical ArticlesCleavage and Deprotection Protocols for Fmoc SPPSLiterature references[1] T. Johnson, et al. (1993) J. Chem. Soc., Chem. Commun., 369. [2] C. Hyde, et al. (1994) Int. J. Peptide Protein Res., 43, 431. [3] L. C. Packman, et al. (1994) Pept. Res., 7, 125. [4] T. Johnson, et al. (1994) Tetrahedron Lett., 35, 463. [5] R. G. Simmonds (1996) Int. J. Peptide Protein Res., 47, 36. [6] T. Johnson, et al. (1995) Lett. Pept. Sci., 1, 11. [7] M. Quibell, et al. (1995) J. Am. Chem. Soc., 117, 11656. [8] M. Quibell, et al. (1996) J. Chem. Soc., Perkin Trans. 1, 1227. [9] M. Quibell, et al. (1994) Tetrahedron Lett., 35, 2237. [10] M. Quibell, et al. (1994) J. Org. Chem., 59, 1745. [11] M. Quibell, et al. (1995) J. Chem. Soc., Perkin Trans. 1, 2019. [12] M. Quibell, et al. (1994) J. Chem. Soc., Chem. Commun., 2343. [13] L. C. Packman (1995) Tetrahedron Lett., 36, 7523. [14] J. Offer, et al. (1996) J. Chem. Soc., Perkin Trans. 1, 175. [15] W. R. Sampson, et al. (1999) J. Peptide Sci., 5, 403.
• Application: Advances in Fmoc solid‐phase peptide synthesis: An overview of recent advancements in Fmoc-SPPS, including the use of specialized Fmoc-amino acids like Fmoc-(FmocHmb)Gly-OH to improve synthesis efficiency and outcomes (J Offer et al., 2016).
• Linkage: Replaces: 04-12-1135
• Analysis Note: Colour (visual): white to slight yellow to beigeAppearance of substance (visual): powderIdentity (IR): passes testPurity (TLC(157A)): ≥ 98 %Purity (TLC(157B)): ≥ 98 %Assay (HPLC, area%): ≥ 98.0 % (a/a)Solubility (1 mmole in 2 ml DMF): clearly solubleAssay (acidimetric): ≥ 95.0 %Water (K. F.): ≤ 1.00 %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