644-90-6

Usage

Uses

Used in Pharmaceutical Industry:
DL-2-Aminooctanoic Acid is used as a reagent for the preparation of 1,5-disubstituted-2-aminoimidazoles, which exhibit antibiotic activity against a variety of bacterial strains, including multi-drug resistant isolates. This application highlights its potential in the development of new antibiotics to combat antibiotic-resistant bacteria.
Used in Chemical Synthesis:
DL-2-Aminooctanoic Acid serves as a reactant in the solution phase parallel synthesis of fenbufen (F247200) and ethacrynic acid (E676000). These compounds have various applications in the medical field, with fenbufen being an anti-inflammatory drug and ethacrynic acid being a diuretic.

InChI:InChI=1S/C8H17NO2/c1-2-3-4-5-6-7(9)8(10)11/h7H,2-6,9H2,1H3,(H,10,11)

Upstream product

• 74-90-8 hydrogen cyanide 
• 40899-00-1 1-amino-heptan-1-ol 
• 880141-72-0 2-formylamino-octanoic acid 
• 2623-82-7 2-bromooctanoic acid 
• 3974-36-5 2-n-hexyl malonic acid 
• 306748-50-5 2-glycylamino-octanoic acid 
• 99310-52-8 (5-ethyl-[2]thienyl)-amino-acetic acid 
• 7647-01-0 hydrogenchloride 
• 5463-91-2 acetylamino-hexyl-malonic acid diethyl ester 
• 10035-10-6 hydrogen bromide 
• 638-45-9 1-Iodohexane 
• 935-30-8 2-azacyclononanone 
• 328-51-8 2-oxooctanoic acid 
• 111-71-7 heptanal 

Downstream Products

• 6271-04-1 4-hexyl-oxazolidine-2,5-dione 
• 92211-95-5 2-((tertbutoxycarbonyl)amino)octanoic acid 
• 112139-11-4 (+/-)-p-nitrophenyl N-(benzyloxycarbonyl)-α-aminooctanoate 
• 112139-14-7 D,L-1-<5'-<(α-aminooctanoyl)amino>-5'-deoxy-β-D-allofuranosyuronic acid>uracil formate 
• 112139-13-6 L,L-1-<5'-<(α-aminooctanoyl)amino>-5'-deoxy-β-D-allofuranosyuronic acid>uracil formate 
• 112139-12-5 (S)-((S)-2-Benzyloxycarbonylamino-octanoylamino)-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid 
• 112139-26-1 (S)-((R)-2-Benzyloxycarbonylamino-octanoylamino)-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid 
• 63219-58-9 DL-α-aminocaprylic acid benzyl ester p-toluene sulfonic acid salt 
• 1325809-25-3 C₁₆H₂₃N₃ 
• 1325809-26-4 C₁₈H₂₇N₃ 
• 1325715-72-7 1-benzyl-5-hexyl-1H-imidazol-2-amine hydrochloride 
• 1325715-73-8 5-hexyl-1-(3-phenylpropyl)-1H-imidazol-2-amine hydrochloride 
• 1218182-47-8 C₁₅H₂₃NO₂ 

Relevant academic research and scientific papers

Hexyl-modified morpholine-2,5-dione-based oligodepsipeptides with relatively low glass transition temperature

Oligodepsipeptides (oDPs), alternating copolymers of an α-amino acid and an α-hydroxy acid, are typically created by ring-opening polymerization (ROP) of morpholine-2,5-dione derivatives (MDs). In general, oDPs exhibit relatively high glass transition temperatures (Tgs) caused by the strong intermolecular H-bonding between amide and ester bonds. So far, it was not reported that variation at α-amino acid moieties in MDs monomers lead to lower Tg. Here we explored whether the thermal properties of the oDPs can be adjusted by introducing a hexyl side chain in the α-hydroxy acid part of the MDs. By synthesizing a MD with an atactic pendant hexyl group at position 3, the influence of a modification at position 6 compared to a modification at position 3 towards ROP was investigated. In both cases the atactic bulky side groups hindered the H-bonding between chain segments resulting in a significant reduction of the Tgs to a temperature around human body temperature (32 and 36 °C) in contrast to ROP of a MD providing a methyl group at position 3 and a Tg ≈ 65 °C. Such oDPs could be interesting candidate materials for biomedical applications such as degradable implants.

New Aspercryptins, Lipopeptide Natural Products, Revealed by HDAC Inhibition in Aspergillus nidulans

Unlocking the biochemical stores of fungi is key for developing future pharmaceuticals. Through reduced expression of a critical histone deacetylase in Aspergillus nidulans, increases of up to 100-fold were observed in the levels of 15 new aspercryptins, recently described lipopeptides with two noncanonical amino acids derived from octanoic and dodecanoic acids. In addition to two NMR-verified structures, MS/MS networking helped uncover an additional 13 aspercryptins. The aspercryptins break the conventional structural orientation of lipopeptides and appear "backward" when compared to known compounds of this class. We have also confirmed the 14-gene aspercryptin biosynthetic gene cluster, which encodes two fatty acid synthases and several enzymes to convert saturated octanoic and dodecanoic acid to α-amino acids.

Biocatalytic asymmetric synthesis of unnatural amino acids through the cascade transfer of amino groups from primary amines onto keto acids

Flee to the hills: An unfavorable equilibrium in the amino group transfer between amino acids and keto acids catalyzed by α-transaminases was successfully overcome by coupling with a ω-transaminase reaction as an equilibrium shifter, leading to efficient asymmetric synthesis of diverse unnatural amino acids, including L-tert-leucine and D-phenylglycine. Copyright

Microwave-assisted synthesis of unnatural amino acids

Microwave irradiation has been proven to be a useful tool in the rapid assembly of racemic unnatural amino acids in only two steps. Additional benefits of this methodology are the commercial availability of the inexpensive starting materials and the high yields and high purities of the final amino acid products.

Synthesis of a library of polycationic lipid core dendrimers and their evaluation in the delivery of an oligonucleotide with hVEGF inhibition

This article follows on from our previous work in the area of non-viral gene delivery using polycationic dendrimers (PCDs). Herein we report on the synthesis and efficacy of a new library of lipid core PCDs in the delivery of the anti-angiogenic oligonucleotide (ODN-1) to retinal pigment epithelial cells. ELISA was used to monitor hVEGF levels in cells transfected with dendriplexes, Cytofectin GSV and control (non-transfected). At 48 h, hVEGF titres had returned to that of the untransfected control for Cytofectin GSV however, a number of dendriplexes continued to exhibit a marked reduction in hVEGF titres.

Method of preparing salicyloylamino acids

A method for preparing salicyloylamino acids is provided. An oligosalicylate and an amino acid are reacted to yield the salicyloylamino acid.

Adsorption of Metal Ions to Surface-Template Resins Prepared with Amphiphilic Styrene Monomers Bearing Amino Carboxylic Acid

Monomer-type functional surfactants, 2-(p-vinylbenzylamino)alkanoic acid (RnAc) and N,N-dialkyl derivatives (RRnNAc), have been used as both a ligand and an emulsifier for the preparation of surface-template resins. The surfactants adsorbed at the toluene-water interface and emulsified divinylbenzene-styrene in a Cu2+ or Zn2+ solution. Emulsion polymerization using a K2S2O8 initiator (80 °C) or by irradiation with γ-rays gave fine particles of 200-800 nm in diameter. Metal-imprinted resins prepared with RnNAc and RRnNAc showed a high adsorptive capacity for the metal ion (surface-template effect). Cu-imprinted resins prepared with R8NAc were 2.69-times as effective for Cu2+ in competitive sorption from a Cu2+-Zn2+ mixture and Zn-imprinted resins were 1.84-times as effective for Zn2+, compared with unimprinted resins. Because of the great emulsifying power, metal-imprinted resins prepared with R8NAc showed the most metal-selective adsorption and the largest capacity among resins prepared with RnNAc and RRnNAc.

Synthesis and anticandidal properties of polyoxin L analogues containing α-amino fatty acids

Analogues of polyoxin L containing amino acids with saturated fatty acid like side chains were synthesized from the benzyloxycarbonyl-protected α-amino fatty acid p-nitrophenyl ester and uracil polyoxin C. Transfer hydrogenolysis using palladium black and formic acid gave diastereomeric, dipeptidyl polyoxin L analogues containing α-aminooctanoic acid (3), α-aminododecanoic acid (4), or α-aminohexadecanoic acid (5) as the amine terminal residue in 40-60% yield. Diastereomers of 3 and 5 were resolved by using high-performance liquid chromatography on a reversed-phase column and designated as 3a, 3b and 5a, 5b. Analogues 3-5 were excellent inhibitors of chitin synthetase from Candida albicans; 4, the best inhibitor, had an ID50 of 0.5 μM. The L,L diastereomers of 3 and 5 were 1-2 orders of magnitude more potent chitin synthetase inhibitors than their D,L homologues. None of the synthetic polyoxin L analogues inhibited transport of trimethionine, but 3a, 4, and 5b caused decreases of 71%, 87%, and 83%, respectively, in the initial rate of uptake of dileucine. Compounds 3-5 were significantly more stable to peptidase degradation than polyoxin L analogues containing naturally occurring α-amino acids. Compound 4 inhibited growth of C. albicans in culture at 40-80 μg/mL. All other analogues were less potent antifungals. The results suggest that synthetic polyoxins can be designed to have increased affinity for a peptide transport system and to have increased stability against intracellular degradation in C. albicans.

SYNTHESIS OF AMINO ACIDS. ALKYLATION OF ALDIMINE AND KETIMINE DERIVATIVES OF GLYCINE ETHYL ESTER UNDER VARIOUS PHASE-TRANSFER CONDITIONS

The Schiff base derived from glycine ethyl ester and p-chlorobenzaldehyde can be alkylated by the ion-pair extraction method as well as under catalytic liquid-liquid or solid-liquid phase-transfer conditions.This imine is compared with the corresponding benzophenone Schiff base.