A,co-Dicarboxylic acids

Stephanou EG (1992) a,cd-dicarboxylic acid salts and a,co-dicarboxylic acids. Photooxidation products of unsaturated fatty acids, present in marine aerosols and marine sediments. Naturwiss 79 28-131. 

Stephanou EG, N Stratigakis (1993) Oxocarboxylic and a,co-dicarboxylic acids photooxidation products of biogenic unsaturated fatty acids present in urban aerosols. Environ Sci Technol 27 1403-1407. 

Self-associative lateral interactions can only occur with the AB-type analytes, chromatographed in sufficiently mild chromatographic conditions. In planar chromatography, this type of lateral interaction was first demonstrated on monocarboxylic fatty acids and a,co-dicarboxylic acids, chromatographed on microcrystalhne cellulose with aid of decalin and 1,4-dioxane as monocomponent eluents, respectively [8,20,23]. 

For a,co-dicarboxylic acids, the anti-Langmuir concentration profiles are pronounced the most for the compounds with the longest ahphatic chains, as shown in Figure 2.8. From the densitograms obtained, it is apparent that a,(0-dicarboxylic acids are more prone to form anti-Langmuir concentration profiles than monocar-boxylic acids. This suggests that lateral interactions are more effective with dicarboxylic acids than with monocarboxylic ones, which seems a natural consequence... 

Oxidative cleavage of 2-nitrocyclohexanones gives a,co-dicarboxylic acids or their esters, as shown in Eq. 5.18.33... 

High amounts of a,co-dicarboxylic acids (mainly suberic, azelaic and sebacic) in a paint sample are indicative of the presence of an aged drying oil. This is because dicarboxylic acids, of which azelaic is the most abundant, are produced during the auto-oxidation of the polyunsaturated acylic chain present in drying oils. 

The El mass spectra of a,co-dicarboxylic acids and co-hydroxycarboxylic acids are characterised by ions arising from the fragmentation of the TMS ester and ether moieties and from fragmentation due to interactions between the two TMS... 

The lipids used in the syntheses of neoglycolipids are often commercially available most of the long-chain carboxylic acids, n-alcanols, n-alcanethiols or n-alkylamines are readily available as well as a.co-dicarboxylic acids, diols or diamines useful for the syntheses of bola-amphiphiles. 

The a,co-dicarboxylic acids formed by oxidation ranged from succinic to dode-canedioic acids, together with a small amount of higher acids. 

Electrolysis of a mixture of two carboxylic acids, R COjH and R2-C02H, leads in addition to the products of normal coupling (R1 — R1 and R2 —R2) to the cross-coupled product (R1 -R2). Similarly if a mixture of a saturated carboxylic acid and a half-ester of an a, co-dicarboxylic acid is electrolysed, there are three main products, viz. a hydrocarbon (6), a mono-ester (7) and a di-ester (8). Normally the three products are readily separable by distillation. Furthermore, by increasing the molar proportion of the monocarboxylic acid, the yield of (7) is improved at the expense of (8). 

A Ballio, EB Chain, FD di Accadia, MF Mastropietro-Cancellieri, G Morpurgo, G Serlupi-Crescenzi, G Sermonti. Incorporation of a, co-dicarboxylic acids as side-chains into the penicillin molecule. Nature 185 97-99, 1960. 

S.K. Callear, M.B. Hursthouse, T.L. ThrelfaU, Cocrystallization of organic a,co-dicarboxylic acids with the cyclic amides 2-pyrrolidmone and 2-imidazolidinone, CrystEngComm 11 (2009) 1609-1614. 

Ballini, R., Curini, M., Epifano, F., Marcotullio, M. C., Rosati, O. A new, modulated, oxidative ring-cleavage of a-nitro cycloalkanones by Oxone. Synthesis of a,co-dicarboxylic acids and a,to-dicarboxylic monomethyl esters. Syn/eff 1998, 1049-1050. 

A portion of these biochemical compounds may be associated with the extracted humic substances. However, as already described, the humin which had been hydrolyzed by 6N HCl at 110°C for 24 hours gave essentially the same oxidative (KMn04) degradation products (aliphatic C4-C14 a,co-dicarboxylic acids as major products) as untreated humin. Moreover, stepwise (eight steps) oxidative (KMn04) degradation of humin produced similar degradation products (aliphatic Cs-C 8 monocarboxylic and C5-C16 a,co-dicarboxylic acids and small amounts of benzenecarboxylic acid Machihara and Ishiwatari, 1980). These facts indicate that the major part of humin forms aliphatic structures with biochemical compounds distributed uniformly in the humin matrix. These compounds are firmly linked within the humin matrix by unknown bonds. 

Salts of a,co-dicarboxylic acids in marine aerosols (Stephanou 1992). 

Linear unsaturated and epoxidized polyesters via enzymatic polymerization were reported as well [58]. For this long-chain symmetrically unsaturated a,co-dicarboxylic acid dimethyl esters (C18, C20, C26) were synthesized using metathesis techniques from 9-decanoic, 10-undecanoic, and 13-tetradecanoic acid methyl esters, respectively. The dicarboxylic acid dimethyl esters were epoxidized via chemoenzymatic oxidation with hydrogen peroxide/methyl acetate and Novozym... 

Warwel, S., Demes, C., and Steinke, G. (2001) Polyesters by lipase-catalyzed polycondensation of unsaturated and epoxidized long-chain a,co-dicarboxylic acid methyl esters with diols. J. Polym. Sci. Part A Polym. Chem., 39 (10), 1601-1609. 

Several co-oxo fatty acids are transformed to the corresponding a,co -dicarboxylic acids, whereas -formylesters of fatty acids are decarboxylated to the co-hydroxy fatty acids and carbon dioxide1111. For several co-oxo fatty acids turnover frequencies (measured as O2 consumption) between 1.8 to 25 s 1 were found. Many P450 systems are multi-component enzymes with small protein cofactors such as putidaredoxin performing the electron mediation between NAD(P)H and the active site of the enzyme. Vilker and coworkers recently were able to show that NADPH can be omitted from the catalytic cycle by direct electrochemical reduction of putidar-... 

Table 8.2. AR INHIBITORY ACTIVITY OF a,co-DICARBOXYLIC ACIDS HOOC - X - COOH ...

Casteonuovo G, Elia V, Velleca F, ViscAEDi G, Thermodynamics of the interaction of a-cyclodextrin with a,co-dicarboxylic acids in aqueous solutions. A calorimetric study at... 

Cronan JE, Lin S (2011) Synthesis of the a,co-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway. Curr Opin Chem Biol 15 407 13... 

Apart from reductive amination and the reaction of -keto acid derivatives with ammonia or amines, there are other carbonyl derivatives that can serve as precursors to amino acids. One sequence begins with the conversion of a,co-dicarboxylic acids... 

Fundamental progress in this field was achieved by the group of Park et al. [28]. In their elegant study, a biocatalytic process was designed and investigated for the production of long-chain a,co-dicarboxylic acids (e.g., CIO) and m-hydroxycarboxylic acids (e.g., C9, Cll, C13) from renewable fatty acids ofplant and animal origin (e.g., oleic acid, ricinoleic acid) which represent important renewable feedstock resources... 

Song, J.-W., Lee, J.-H., Bornscheuer, U.T., Park, J.-B., 2014. Microbial synthesis of medium-chain a,co-dicarboxylic acids and co-amincarboxylic acids from renewable long-chain fatty adds. Adv. Synth. Catal. 356,1782-1788. 

---