8.52309

Fmoc-ACA-OH

Novabiochem^®

• Synonym(e): 7-N-Fmoc-aminocoumarin-4-acetic acid
• Empirische Formel (Hill-System): C₂₆H₁₉NO₆
• CAS-Nummer: 378247-75-7
• Molekulargewicht: 441.43
• MDL-Nummer: MFCD13195295
• 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: aromatic amine
• Lagertemp.: 2-8°C
• SMILES String: N(c4cc5[o][c](cc(c5cc4)CC(=O)O)=O)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C26H19NO6/c28-24(29)11-15-12-25(30)33-23-13-16(9-10-17(15)23)27-26(31)32-14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-10,12-13,22H,11,14H2,(H,27,31)(H,28,29)
• InChIKey: RCUKLQDGAASIAX-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

Fmoc-ACA-OH is a useful tool for the SPPS of AMC fluorogenic protease substrates by Fmoc SPPS. Fmoc-ACA-OH ^[1] must be first loaded onto a Wang-type resin. Any unreacted linker hydroxyls must be capped using acetic anhydride. Following Fmoc removal, the first amino acid should be coupled with HATU/collidine ^[2]. Insertion of ACA into the middle of a peptide provides fluorogenic substrates for endopeptidases ^[3]. Treatment of the ACC peptide obtained after TFA cleavage with an aqueous base causes facile decarboxylation and formation of the AMC peptide.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Chromogenic Labeling of Synthetic Peptides

Literature references

^[1] J. L. Harris, et al. (2000) Proc. Natl. Acad. Sci. USA, 97, 7754.
^[2] D. J. Maly, et al. (2002) J. Org. Chem., 67, 910.
^[3] C. M. Salisbury, et al. (2002) J. Am. Chem. Soc., 124, 14868.

Hinweis zur Analyse

Farbe (visuell): weiß bis schwach gelb bis rosastichig
Aussehen der Substanz (visuell): Pulver
Identität (IR): entspricht
Reinheit (DC(CMA1)): ≥ 98 %
Gehalt (HPLC, Fl.%): ≥ 95.0 % (a/a)
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