2-Amino octanoic acid

Other abbreviations used Prw, n-propyl Pr , i-propyl Bun, n-butyl Bft, i-butyroyl Fe, fenchyl Cap, capryline=or-amino-octanoic acid aThr, aWothreonine HyNle, (3-hydroxynorleucine MPA, methylphenethyl-amine, HMPA, hydroxymethylphenethylamine Ama, aminomalonic acid. 

Main, A.J., Bhagwat, S.S.. Boswell, C., Goldstein, R., Gude, C., Cohen, D.S., Rumess, P, Lee, W., and Louzan, M., Thromboxane receptor antagonism combined with thromboxane synthase inhibition. Part 3. Pyridinylalkyl-substituted 8-[(arylsulfonyl)amino]octanoic acids, J. Med. Chem., 35, 4366, 1992. 

L 2 aminobutyric acid can substitute for L-alanine (CyV). N-Methyl-L-leucine in position 4 may be replaced by N-methyl-L isoleucine (Cy29) or by L-valine in CyQ and CyS. Regarding possible biosynthetic pathways, variations at position 1 are of special interest CyF and CyK contain deoxy-MeBmt, whereas N-methyl-L-Z-amino-octanoic acid is found in CyZ, Both building units probably stem from a common precursor of the genuine amino acid (4R) 4 l E) 2 butenyI] 4 fnethYl L-threonine (Bmt). A full exchange of this characteristic structural unit by N-methyl-L-leucine is observed in CyO. At present, positions 3 and 8 containing sarcosine and D-alanine, respectively, are the only conserved building units. 

The sodium salt of succinimide reacts with a,o)-dibromide such as 4.93 to give 4.94. In a second step, the enolate of a-phenyl nitrile displaced the bromide moiety in 4.94 to give 4.95. Acid hydrolysis converted the nitrile to an acid and the imide to an amine, leading to 4.96. Reaction of 4.94 (n = 4) with the indicated nitrile (R = H) led to a 57% yield of 2-phenyl-6-aminohexanoic acid (4.96a). Similarly prepared were 2-phenyl-7-aminoheptanoic acid 4.96b) in 68% yield 2-phenyl-8-amino-octanoic acid 4.96c) in 68% yield 2-phenyl-10-aminodecanoic acid 4.96d) in 44% yield and, 2-phenyl-12-aminododecanoic acid 4.96e) in 26% yield, all with R = H.45 Many other nitriles were used in this sequence to give a wide variety of phenyl... 

Fles et al [64], starting with (/ )(-)-4-methyl-6-phthalimidohexanoic acid, prepared (/ )(-)-6-methyl-8-amino-octanoic acid and polymerized it to OA (/ )(+)-6-methyl-nylon-8. Strong solvent dependence of specific rotation in a mixture of w-cresol and chloroform was observed for the polymer and for the model compound (/ )(+)-6-methyl-8-acetamido-octanoyl-7V-methylamide. 

CN 6-(aceiylthio)-8-[[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-l-(2-hydroxycthyl)-l-propenyl]dithio]octanoic acid methyl ester... 

The figures give the number of amino acid residues per molecule. The + and — signs indicate the presence or absence of the amino acids. MOA — (-f )-6-methyloctanoic acid lOA = Iso-octanoic acid (6-methylheptanoic acid). 

Karahdian et al. (1985a,b) demonstrated the production of l-octen-3-ol, 8-nonen-2-one, 3-octanone, 3-octanol and octanoic acid from linoleic acid and linolenic acid. The use of microbially produced fatty acids for characterization of mold fungi has been suggested (Blomquist et al., 1992). Lipolysis of triglycerides or amino acids may lead to the production of compounds such as 2-methylpropanoic acid, butanoic acid, 2-methylbu-tanoic acid, pentanoic acid, hexanoic acid and octanoic acid (Jolivet and Belin, 1993). The presence of different lipids and lipases in different fungi (Ha and Lindsay, 1993) and under different environmental conditions may explain a great deal of the variation in the volatile compounds produced. 

To make SNURs such as the one appUcable to octanoic acid, hydrazide even more difficult to interpret, the procedure describing the bona fide letter is in another SNUR instead of one of the subparts of the SNUR regulations that have general applicability. The reference in the octanoic acid, hydrazide SNUR to determining if a use of the substance is a significant new use by following the provisions of 40 C.F.R. 721.1725(b)(1) is in fact a reference to the bona fide letter procedure set out in the SNUR for benzoic acid, 3,3 -methylenebis [6 amino-, di-2-propenyl ester]. ... 

A fatty acid precursor octanoic acid (capric acid) is employed, which is subsequently transformed into the ketoaldehyde through successive oxidation and reduction steps (Fig. 26.2). The resulting ketoaldehyde acts as a substrate for a transamination reaction the amino moiety is derived from L-alanine [1, 8, 21, 30, 33, 45,47,49, 50,55,68,70,72, 74, 75]. The ultimate transformation leads to the formation of imine, giving the heterocyclic ring present in y-coniceine, and then reduction of the coniine, as shown in Fig. 26.2. 

Later experimental work provided evidence that the 8-carbon polyketoacid intermediate in the synthesis of y-coniceine is derived from octanoic acid since this acid was shown to be readily incorporated into coniine. Further work indicated that 5-keto-octanoic acid and 5-keto-octanal were produced during the biosynthesis of y-coniceine. A transaminase (L-alanine 5-keto-octanal aminotransferase) was obtained from C. maculatum. This transaminase catalyzes the reaction between 5-keto-octanal with L-alanine as the amino group donor to form the piperidine ring and the propyl side chain. Another C. maculatum alkaloid, A-methylconiine, was shown to be produced by another enzyme from the plant a coniine methyltransferase which acts as a transmethylator utilizing 5-adenosyl-L-methionine as a methyl group donor. 

O 18 Octanedioic acid. See Suberic acid. O 19 Octanoic acid, 8-amino-, polyamide... 

J. Ten Brink (Academic Hospital V. U. Amsterdam). Normal values were obtained from 58 children in whom fatty acid oxidation defects were excluded by our usual protocol of amino acids, AC and carnitine in blood, and organic adds in urine. None of the controls received a spedal diet and their blood samples were obtained after an overnight fast (children) or at the end of their usual fasting period (infants). When enough sample was available, levels of octanoic acid were measured in plasma by GC/MS, as described. Mutation analysis was performed by Drs. B. Storstein Andersen and N. Gregersen at the Centte for Medical Molecular Biology, University of Aarhus, Detunark. 

Coniine from the hemlock plant Conium maculatum is a simple example of an alkaloid, although its biosynthesis is unusual. It was thought that coniine would be derived from the amino-acid lysine, but labelled lysine was not converted to coniine. It is unusual in being derived from a type I polyketide (Chapter 4). Both [6- C]-5-oxo-octanoic acid and [6- C]-5-oxo-octanal are well-incorporated into labelled coniine (Figure 9.3). 

Isolated from the species Lyngbya semiplena collected at a shallow depth (1-3 m) in Wewak Bay, Papua New Guinea, the wewakpeptins A-D are cytotoxic depsipeptides which contain many nonribosomal amino acids such as 2,2-dimethyl-3-hydroxy-octanoic acid (Dhoaa) and 2,2-dimethyl-3-hydroxy-octynoic (Dhoya), as well as N-methy-lated amino adds such as N-methylvahne and N-methyl-alanine. A second lactone implies 2-hydroxy-isovaleric add (Hiva) for wewakpeptins A and B, and phenyllactic add (Pla) for wewakpeptins C and D. Wewakpeptins A and B are approximately tenfold more cytotoxic towards the lung cancer NCI-H460 than are wewakpeptins C and D (Han et al, 2005b). 

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