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8.52060

Sigma-Aldrich

Fmoc-(FmocHmb)Ala-OH

Novabiochem®

Synonym(s):

Fmoc-(FmocHmb)Ala-OH, N-α-Fmoc-N-α-(2-Fmoc-oxy-4-methoxybenzyl)-L-alanine

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About This Item

Empirical Formula (Hill Notation):
C41H35NO8
CAS Number:
148515-85-9
Molecular Weight:
669.72
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

200

product line

Novabiochem®

Assay

≥95.0% (HPLC)
≥98% (TLC)

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

InChI

1S/C41H35NO8/c1-25(39(43)44)42(40(45)48-23-36-32-15-7-3-11-28(32)29-12-4-8-16-33(29)36)22-26-19-20-27(47-2)21-38(26)50-41(46)49-24-37-34-17-9-5-13-30(34)31-14-6-10-18-35(31)37/h3-21,25,36-37H,22-24H2,1-2H3,(H,43,44)/t25-/m0/s1

InChI key

NABBLRADDJWAHI-VWLOTQADSA-N

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 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.

Linkage

Replaces: 04-12-1127

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(011C)): ≥ 98 %
Purity (TLC(157A)): ≥ 98 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Water (K. F.): ≤ 1.50 %
Solubility (1 mmole in 2 ml DMF): clearly soluble

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’.

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Protocols

Overcoming 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.

Overcoming 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.

Overcoming 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.

Overcoming 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.

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