8.52064
Fmoc-(FmocHmb)Gly-OH
Novabiochem®
Synonym(s):
Fmoc-(FmocHmb)Gly-OH, N-α-Fmoc-N-α-(2-Fmoc-oxy-4-methoxybenzyl)-glycine
Sign Into View Organizational & Contract Pricing
All Photos(1)
About This Item
Empirical Formula (Hill Notation):
C40H33NO8
CAS Number:
Molecular Weight:
655.69
UNSPSC Code:
12352209
NACRES:
NA.22
Recommended Products
Quality Level
product line
Novabiochem®
Assay
≥95.0% (acidimetric)
≥98% (TLC)
≥98.0% (HPLC)
form
powder
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
manufacturer/tradename
Novabiochem®
application(s)
peptide synthesis
functional group
Fmoc
storage temp.
2-8°C
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 Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Literature 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.
Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Literature 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 beige
Appearance of substance (visual): powder
Identity (IR): passes test
Purity (TLC(157A)): ≥ 98 %
Purity (TLC(157B)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 95.0 %
Water (K. F.): ≤ 1.00 %
To see the solvent systems used for TLC of Novabiochem® products please click here.
Appearance of substance (visual): powder
Identity (IR): passes test
Purity (TLC(157A)): ≥ 98 %
Purity (TLC(157B)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (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
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service