8-Aminooctanoic acid

Chemical Properties

WHITE TO SLIGHTLY BEIGE CRYSTALLINE POWDER

Uses

8-Aminooctanoic acid is involved in the preparation of lactams using enzyme catalyzed aminolysis.

Definition

ChEBI: 8-aminooctanoic acid is an omega-amino fatty acid that is octanoic acid which carries an amino group at position 8. It has a role as a human metabolite. It is a medium-chain fatty acid and an omega-amino fatty acid.

Reactivity Profile

Other lactams such as butyrolactam, d-valerolactam, and dimer and trimer lactams can be formed from enzymatic reactions of 4-aminobutanoic acid, 5-aminovaleric acid, and 8-aminooctanoic acid using N435 as the catalyst. For reactions using 8-aminooctanoic acid as the substrate, N435 did not catalyze the formation of caprylolactam. Instead, the corresponding dimer and trimer lactams were formed. The formation of macrocyclic bislactams from reactions between diesters and diamines using porcine pancreatic lipase as the catalyst was previously reported. However, in the enzymatic reaction of 8-aminooctanoic acid using N435, different macrocyclic dimer and trimer lactams were formed in a ratio of 3:2. The ratio was calculated from the mass spectrometric peak intensities of the product[2].

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

In a 1 l flask with paddle stirrer, internal thermometer and reflux condenser, 142.6 g (1 mol) of 2-azacyclononanone and 110 g (1 mol) of about 36 wt.-% sodium hydroxide solution are boiled under reflux for 4 hours. The solution is subsequently cooled to about 80 °C and mixed with Lewatit SP-112. After one hour, the acidic ion exchanger is filtered. 500 g of 2-Propanol is added dropwise to the mixture at 80 °C, and the homogeneous solution is slowly cooled to -5 °C. The precipitated solid is filtered and washed with 50 g of 2-propanol. After drying at 85 °C and 20 mbar, 8-Aminooctanoic acid is obtained as a fine colorless powder. A colorless powder. Yield: 127 g (80%). Melting point: 191-193 °C (Lit.: 194 °C).

structure and hydrogen bonding

References

[1] A J Dobson, R E Gerkin. “8-Aminocaprylic acid.” Acta crystallographica. Section C, Crystal structure communications 54 ( Pt 7) (1998): 969–72.
[2] E. Stavila, K. Loos. “Synthesis of lactams using enzyme-catalyzed aminolysis.” Tetrahedron Letters 54 5 (2013): Pages 370-372.