8.52060

Fmoc-(FmocHmb)Ala-OH

Novabiochem^®

• Synonym(e): N-α-Fmoc-N-α-(2-Fmoc-oxy-4-methoxybenzyl)-L-alanine
• Empirische Formel (Hill-System): C₄₁H₃₅NO₈
• CAS-Nummer: 148515-85-9
• Molekulargewicht: 669.72
• UNSPSC-Code: 12352209
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 200
• Produktlinie: Novabiochem^®
• Assay: ≥95.0% (HPLC); ≥98% (TLC)
• Form: powder
• Eignung der Reaktion: reaction type: Fmoc solid-phase peptide synthesis
• Hersteller/Markenname: Novabiochem^®
• Anwendung(en): peptide synthesis
• Funktionelle Gruppe: Fmoc
• Lagertemp.: 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
• InChIKey: NABBLRADDJWAHI-VWLOTQADSA-N

Beschreibung

Allgemeine Beschreibung

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.

Verlinkung

Replaces: 04-12-1127

Hinweis zur Analyse

Farbe (visuell): weiß bis schwach gelb bis beige
Aussehen der Substanz (visuell): Pulver
Identität (IR): entspricht
Enantiomerenreinheit: ≥ 99.5 % (a/a)
Reinheit (DC(011C)): ≥ 98 %
Reinheit (DC(157A)): ≥ 98 %
Gehalt (HPLC, Fl.%): ≥ 95.0 % (a/a)
Wasser (K. F.): ≤ 1.50 %
Löslichkeit (1 mmol in 2 ml DMF): klar löslich
DC-Bedingungen gemäß den Angaben unseres Hauptkataloges

Rechtliche Hinweise

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

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 2
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable