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8.52061

Sigma-Aldrich

Fmoc-(FmocHmb)Leu-OH

Novabiochem®

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Synonym(s):
Fmoc-(FmocHmb)Leu-OH, N-α-Fmoc-N-α-(2-Fmoc-oxy-4-methoxybenzyl)-L-leucine
Empirical Formula (Hill Notation):
C44H41NO8
CAS Number:
Molecular Weight:
711.80

Quality Level

product line

Novabiochem®

assay

≥90.0% (acidimetric)
≥95% (TLC)
≥96.0% (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

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Fmoc-(FmocHmb)Leu-OH Novabiochem®

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Fmoc-(FmocHmb)Gly-OH

Fmoc-(Dmb)Gly-OH Novabiochem®

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Fmoc-(Dmb)Gly-OH

assay

≥90.0% (acidimetric), ≥96.0% (HPLC), ≥95% (TLC)

assay

≥97.0% (HPLC), ≥98% (TLC)

assay

≥95.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)

assay

≥94.0% (acidimetric), ≥98% (TLC), ≥99.0% (HPLC)

functional group

Fmoc

functional group

Boc, amine

functional group

Fmoc

functional group

Fmoc

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-10 to -25°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

General description

Hmb protection of amide bonds has been shown to inhibit aggregation of "difficult" peptides in 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 carboxy 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., 369.
[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.

Linkage

Replaces: 04-12-1129

Analysis Note

Color (visual): white to off white
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(011A)): ≥ 95 %
Assay (HPLC, area%): ≥ 96.0 % (a/a)
Solubility (1 mmole in 2 ml CH₂Cl₂): clearly soluble
Assay (acidimetric): ≥ 90.0 %

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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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