8.52061

Fmoc-(FmocHmb)Leu-OH

Novabiochem^®

• Synonym(e): Fmoc-(FmocHmb)Leu-OH, N-α-Fmoc-N-α-(2-Fmoc-oxy-4-methoxybenzyl)-L-leucine
• Empirische Formel (Hill-System): C₄₄H₄₁NO₈
• CAS-Nummer: 148515-87-1
• Molekulargewicht: 711.80
• MDL number: MFCD00278812
• UNSPSC Code: 12352209
• NACRES: NA.22

Eigenschaften

• Quality Segment: 200
• 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
• SMILES string: N([C@@H](CC(C)C)C(=O)O)(Cc4c(cc(cc4)OC)OC(=O)OCC5c6c(cccc6)c7c5cccc7)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C44H41NO8/c1-27(2)22-40(42(46)47)45(43(48)51-25-38-34-16-8-4-12-30(34)31-13-5-9-17-35(31)38)24-28-20-21-29(50-3)23-41(28)53-44(49)52-26-39-36-18-10-6-14-32(36)33-15-7-11-19-37(33)39/h4-21,23,27,38-40H,22,24-26H2,1-3H3,(H,46,47)/t40-/m0/s1
• InChI key: ZFZVDKKVQNKRCW-FAIXQHPJSA-N

Beschreibung

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.

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.

Other Notes

Replaces: 04-12-1129

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable