12-Aminolauric acid
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12-Aminolauric acid

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12-Aminolauric Acid is an amino acid used as a reagent in organic synthesis of several compounds including phenylbutazone which is a new long-acting agent which displays improved pharmacokinectics based on human serum albumin as a drug carrier.

Category
Other Unnatural Amino Acids
Catalog number
BAT-007780
CAS number
693-57-2
Molecular Formula
C12H25NO2
Molecular Weight
215.34
12-Aminolauric acid
IUPAC Name
12-aminododecanoic acid
Synonyms
12-Aminolauric acid; 12-Ado-OH; 12-Aminododecanoic acid; 12-AMINO-DODECANOIC ACID; Dodecanoic acid, 12-amino-; omega-Aminolauric acid; Omega-Aminododecanoic acid; 12-aminododecanic acid; H-Adod(12)-OH
Related CAS
95418-77-2 (deleted)
Appearance
Off-white powder
Purity
≥ 99% (Titration)
Density
0.957±0.06 g/cm3 (Predicted)
Melting Point
185-187 °C
Boiling Point
349.7±15.0 °C (Predicted)
Storage
Store at -20 °C
InChI
InChI=1S/C12H25NO2/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h1-11,13H2,(H,14,15)
InChI Key
PBLZLIFKVPJDCO-UHFFFAOYSA-N
Canonical SMILES
C(CCCCCC(=O)O)CCCCCN
1. High yield synthesis of 12-aminolauric acid by "enzymatic transcrystallization" of omega-laurolactam using omega-laurolactam hydrolase from Acidovorax sp. T31
Yasuhisa Fukuta, Hidenobu Komeda, Yoichi Yoshida, Yasuhisa Asano Biosci Biotechnol Biochem. 2009 May;73(5):980-6. doi: 10.1271/bbb.80551. Epub 2009 May 7.
The genes encoding omega-laurolactam hydrolases from Cupriavidus sp. T7, Acidovorax sp. T31, Cupriavidus sp. U124, and Sphingomonas sp. U238 were cloned and sequenced. Nucleotide and amino acid sequence analysis of the four genes indicated that the primary structures of these omega-laurolactam hydrolases are significantly similar to the 6-aminohexanoate-cyclic-dimer hydrolase (EC 3.5.2.12). These genes were expressed in Escherichia coli, and the omega-laurolactam hydrolysing activity of the recombinant enzymes was compared with that of 6-aminohexanoate-cyclic-dimer hydrolase from Arthrobacter sp. KI72. The enzyme from Acidovorax sp. T31 was most successfully expressed in E. coli. Cell-free extract of the recombinant strain was used for the synthesis of 12-aminolauric acid from omega-laurolactam by "enzymatic transcrystallization," because crystalline omega-laurolactam added into the enzyme solution was converted to crystalline 12-aminolauric acid (> or =97.3% yield). Under the optimum conditions, 208 g/l of 12-aminolauric acid was produced in 17 h. The resulting pure product was identical to authentic 12-aminolauric acid.
2. Reductive defluorination of Perfluorooctanesulfonic acid (PFOS) by hydrated electrons generated upon UV irradiation of 3-Indole-acetic-acid in 12-Aminolauric-Modified montmorillonite
Alex Kugler, Hailiang Dong, Chen Li, Cheng Gu, Charles E Schaefer, Youn Jeong Choi, Danielle Tran, Morgan Spraul, Christopher P Higgins Water Res. 2021 Jul 15;200:117221. doi: 10.1016/j.watres.2021.117221. Epub 2021 May 9.
Per-and poly-fluoroalkyl substances (PFASs) are a class of persistent compounds that are resistant to degradation. Here we developed an effective method of degrading perfluorooctanesulfonate (PFOS) by hydrated electrons (eaq-) that are generated from 3-indole-acetic-acid (IAA) upon UV irradiation. The method takes advantage of spatial proximity of IAA and PFOS by their co-sorption to an organic polymer, 12-aminolauric acid (ALA), which was pre-intercalated into the interlayer space of an expandable clay mineral, montmorillonite. The interlayer spacing of this clay nanocomposite is greatly expanded relative to unmodified montmorillonite. The maximum adsorption capacity of IAA and PFOS is 168 and 1550 mmol/kg, respectively. This process achieved 40-70% defluorination of a 10 ppm PFOS solution at neutral pH in a 325 mL vessel. The presence of bicarbonate and chloride ions, or natural groundwater showed a minimal impact on PFOS degradation. Based on identification of prominent degradation products, a degradation pathway is proposed, where the primary degradation process is breakage of the C-F bonds (with fluorine replaced by hydrogen), with some cleavage of the CC bond. This approach provides an alternative for treating concentrated PFAS solutions under ambient conditions.
3. The screening, characterization, and use of omega-laurolactam hydrolase: a new enzymatic synthesis of 12-aminolauric acid
Yasuhisa Asano, Yasuhisa Fukuta, Yoichi Yoshida, Hidenobu Komeda Biosci Biotechnol Biochem. 2008 Aug;72(8):2141-50. doi: 10.1271/bbb.80210. Epub 2008 Aug 7.
Several omega-laurolactam degrading microorganisms were isolated from soil samples. These strains were capable of growing in a medium containing omega-laurolactam as sole source of carbon and nitrogen. Among them, five strains (T7, T31, U124, U224, and U238) were identified as Cupriavidus sp. T7, Acidovorax sp. T31, Cupriavidus sp. U124, Rhodococcus sp. U224, and Sphingomonas sp. U238, respectively. The omega-laurolactam hydrolyzing enzyme from Rhodococcus sp. U224 was purified to homogeneity, and its enzymatic properties were characterized. The enzyme acts on omega-octalactam and omega-laurolactam, but other lactam compounds, amides and amino acid amides, cannot be substrates. The enzyme gene was cloned, and the deduced amino acid sequence showed high homology with 6-aminohexanoate-cyclic-dimer hydrolase (EC 3.5.2.12) from Arthrobacter sp. KI72 and Pseudomonas sp. NK87. Enzymatic synthesis of 12-aminolauric acid was performed using partially purified omega-laurolactam hydrolase from Rhodococcus sp. U224.
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