8.52072

Fmoc-Asp-OAll

Novabiochem^®

• Synonym(e): N-α-Fmoc-L-aspartic acid α-allyl ester
• Empirische Formel (Hill-System): C₂₂H₂₁NO₆
• CAS-Nummer: 144120-53-6
• Molekulargewicht: 395.41
• MDL-Nummer: MFCD00467715
• UNSPSC-Code: 12352209
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 200
• Produktlinie: Novabiochem^®
• Assay: ≥97.0% (acidimetric); ≥98% (TLC); ≥98.0% (HPLC)
• Form: powder
• Eignung der Reaktion: reaction type: Fmoc solid-phase peptide synthesis
• Hersteller/Markenname: Novabiochem^®
• mp (Schmelzpunkt): 95 °C (decomposes)
• Anwendung(en): peptide synthesis
• Funktionelle Gruppe: carboxylic acid
• Lagertemp.: 2-30°C
• InChI: 1S/C22H21NO6/c1-2-11-28-21(26)19(12-20(24)25)23-22(27)29-13-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h2-10,18-19H,1,11-13H2,(H,23,27)(H,24,25)/t19-/m0/s1
• InChIKey: ZJMVIWUCCRKNHY-IBGZPJMESA-N

Beschreibung

Allgemeine Beschreibung

Orthogonally-protected building block for the synthesis of head-to-tail cyclic peptides ^[1,2,3,4,5] by Fmoc SPPS. The α-allyl ester can be selectively removed in the presence of Fmoc- and tBu-based protecting groups by treatment with Pd(Ph₃P)₄/ CHCl₃/AcOH/NMM ^[6], thereby facilitating the synthesis of branched esters, amides, lactones and lactams incorporating an aspartyl unit.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] W. Bannwarth, et al. (1992) Tetrahedron Lett., 33, 4557.
^[2] F. Albericio, et al. (1993) Tetrahedron Lett., 34, 1549.
^[3] J. Eichler, et al. (1994) Pept. Res., 7, 300.
^[4] J. Eichler, et al. in ′Peptides 1994, Proc. 23rd European Peptide Symposium′, H. Maia (Eds), ESCOM, Leiden, 1994, pp. 461.
^[5] J. Eichler, et al. in ′Solid Phase Synthesis & Combinatorial Libraries, 4th International Symposium′, R. Epton (Eds), Mayflower Scientific Ltd., Birmingham, 1996, pp. 201.
^[6] S. A. Kates, et al. in ′Peptides, Chemistry, Structure & Biology, Proc. 13th American Peptide Symposium′, ESCOM, Leiden, 1994, pp. 113.

Verlinkung

Replaces: 04-12-1157

Hinweis zur Analyse

Farbe (visuell): weiß bis schwach gelb bis beige
Aussehen der Substanz (visuell): Pulver
Identität (IR): entspricht
Enantiomerenreinheit: ≥ 99.0 % (a/a)
Reinheit (DC(CMA2)): ≥ 98 %
Reinheit (DC(157A)): ≥ 98 %
Gehalt (HPLC, Fl.%): ≥ 98.0 % (a/a)
Löslichkeit (1 mmol in 2 ml DMF): klar löslich
Gehalt (acidimetrisch): ≥ 97.0 %
Wasser (K. F.): ≤ 1.5 %
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 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable