Skip to Content
Merck
All Photos(1)

Key Documents

8.52064

Sigma-Aldrich

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


About This Item

Empirical Formula (Hill Notation):
C40H33NO8
CAS Number:
Molecular Weight:
655.69
UNSPSC Code:
12352209
NACRES:
NA.22

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.

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.

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.

Visit the Document Library

Protocols

The ease of assembly of a given peptide sequence is hard to predict, which makes peptide synthesis challenging. Review methods and reagents for avoiding aggregation in solid-phase peptide synthesis.

The ease of assembly of a given peptide sequence is hard to predict, which makes peptide synthesis challenging. Review methods and reagents for avoiding aggregation in solid-phase peptide synthesis.

The ease of assembly of a given peptide sequence is hard to predict, which makes peptide synthesis challenging. Review methods and reagents for avoiding aggregation in solid-phase peptide synthesis.

The ease of assembly of a given peptide sequence is hard to predict, which makes peptide synthesis challenging. Review methods and reagents for avoiding aggregation in solid-phase peptide synthesis.

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