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Lactobionic Acid: Significance and Application in Food and Pharmaceutical Minal, N., Bharwade, Smitha Balakrishnan*, Nisha N

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Lactobionic Acid: Significance and Application in Food and Pharmaceutical Minal, N., Bharwade, Smitha Balakrishnan*, Nisha N Intl. J. Food. Ferment. 6(1): 25-33, June 2017 © 2017 New Delhi Publishers. All rights reserved DOI: 10.5958/2321-712X.2017.00003.5 Lactobionic Acid: Significance and Application in Food and Pharmaceutical Minal, N., Bharwade, Smitha Balakrishnan*, Nisha N. Chaudhary and A.K. Jain SMC College of Dairy Science, AAU, Anand, India *Corresponding author: [email protected] Abstract Lactose has long been used as a precursor for the manufacture of high-value derivatives with emerging applications in the food and pharmaceutical industries. This review focuses on the main characteristics, manufacturing methods, physiological effects and applications of lactobionic acid. Lactobionic acid is a product obtained from lactose oxidation, with high potential applications as a bioactive compound. Recent advances in tissue engineering and application of nanotechnology in medical fields have also underlined the increased importance of this organic acid as an important biofunctional agent. Keywords: Lactobionic acid, oxidation, physiological effects, applications Carbohydrates have been used in the manufacture biocompatibility, biodegradability, nontoxicity, of bulk and fine chemicals, and are viewed as a chelating, amphiphilic and antioxidant properties renewable feedstock for the ‘green chemistry of the (Alonso et al., 2013). future. Lactose, a unique disaccharide, occurring extensively in the mammalian milk plays an CHEMISTRY important role in nutrition. Most of the lactose that Lactobionic acid (4-0-β-D-galactopyranosyl-D- is manufactured on an industrial scale is produced gluconic acid) belongs to the aldobionic family of acids from the whey derived from the production of cheese, (Pezzotti and Therisod, 2006). Chemically lactobionic casein or paneer by using drying, crystallization and acid comprises a galactose moiety linked with a purification technologies. gluconic acid molecule via an ether-like linkageand However the use of lactose is limited in many featured by the presence of multifunctional groups. applications, because of its low sweetness and Thus it acts as a metal ion chelator and can sequester solubility, as well as due to the intolerance of calcium (Alonso et al., 2013). It has a molecular some population segments (Gutierrez et al., 2011). weight of 358.3 Da with pKa 3.6 (Armarego and Lactose can be converted to various derivatives Chai, 2009). From a nutritional point of view, this like lactobionic acid, lactulose, lactitol, galacto- substance may be considered a low calorie sweetener oligosaccharides, epilactose etc., using laboratory or which provides only 2 kcal/g (Schaafsma, 2008). industrial processes. Lactobionic acid is produced Lactobionic acid appears as a white solid powder by oxidation of lactose. It is widely used in food which is freely soluble in water and slightly soluble and in pharmaceutical field due to its excellent in anhydrous ethanol and methanol. It has a melting Minal et al. point in the range of 128-130ºC (Alonso et al., 2013). hydrolyzed (its carbonyl group) by a lactonase into Lactobionic acid can be dehydrated to a lactone. It lactobionic acid (Alonso et al., 2012; Nishizuka and is hygroscopic in nature. Its superior water-retention Hayaishi, 1962). ability is valuable for cosmetic applications (Playne While the production of lactobionic acid from lactose and Crittenden, 2009). Lactobionic acid and its by using filamentous fungi, gives only 50% yield mineral salts (mainly Na, Ca and K lactobionate) are after 120 h, which suggests the presence of residual commercially produced for industrial and medical lactose oxidase activity in this fungus (Pedruzzi et al., applications, as well as for research purpose (Nakano 2011; Malvessi et al., 2013). In addition, the lactose- et al., 2010). oxidizing ability has been also found in a red algae, which are capable of oxidizing diverse carbohydrates PRODUCTION at an optimum pH of 5.0 (Murakami et al., 2003; The selective conversion of lactose to lactobionic acid Alonso et al., 2011). Oxidation of lactose by using consists of the oxidation of the free aldehyde group Acetobacter orientalis gives 97 to 99% yield under of glucose on the lactose molecule to the carboxylic resting cell conditions in nutrient rich media at the group. Several processes including biocatalytic, shake flask scale (Kiryuet al., 2012). electrochemical and heterogeneous catalytic The oxidation of lactose to lactobionic acid by acetic oxidations have been investigated for the production acid bacteria, such as Gluconobacter cerinus UTBC-427 of lactobionic acid. showed the highest lactose oxidizing activity of the Biocatalytic oxidation screened microorganisms (Oe et al., 2008). This latter GRAS microorganism has been recently selected by The biocatalytic production of lactobionic acid Unitika Company in Japan as microbial platform comprises the oxidation of lactose by means of for lactobionic acid industrial bio-production under specific enzymes or by using microorganisms as resting cell conditions (Kimura, 2012). biocatalysts. The general reaction mechanism, involves the formation of lactobiono-δ-lactone as Enzymatic synthesis an intermediate product, which is hydrolyzed to Enzymatic catalysis produces higher lactobionic lactobionic acid (Nakano et al., 2010). The process is acid, yields, and productivities than microbial generally carried out at mild temperature conditions fermentation, but enzymes are rather unstable under 25-50ºC, and the pH must be kept constant during enzymatic production process conditions (Nordkvist reaction by adequate addition of a Na, Ca or K base, et al., 2007). Lactose oxidizing enzymes are glucose- the product can be lactobionic acid or its salts. When fructose dehydrogenase, cellobiose dehydrogenase lactobionate salts are produced, the solution can (Van Hecke et al., 2009), and carbohydrate oxidase be passed through cation exchange resins to obtain (Gutiérrez et al., 2012), have been used for lactobionic a lactobionic acid solution, which can be further acid production, but technological challenges are concentrated and crystallized to produce pure many that require coenzyme regeneration and lactobionic acid. enzyme inactivation mostly by the formation of Microbial production H2O2, which has to be reduced, by the addition of catalase (Hua et al., 2007) in addition, redox mediators Pseudomonas species are the main bionic producer required they may be incompatible with the intended microorganisms, lactobionic acid is formed via the use of the product (Ludwig et al., 2004). lactose oxidation pathway, in which a membrane bound dehydrogenase enzyme initially catalyzes Cellobiose dehydrogenase has been the mostly used the oxidation of the lactose to a lactone intermediate enzyme for the synthesis lactobionic acid, it is an (lactobiono-δ-lactone) which is subsequently extracellular enzyme produced by several fungi, Print ISSN: 2319-3549 26 Online ISSN: 2321-712X Lactobionic Acid: Significance and Application in Food and Pharmaceutical like Sclerotiumrolfsii, Phanerochaete chrysosporium, catalysts was first successfully performed by Hendriks and Trametes versicolor (Zamocky et al., 2006; Kiryu et al., (1990). To strip off the dissolved oxygen, and et al., 2008). The enzyme requires a redox mediator to maintain the overall reaction kinetics, Periodic like 2, 2-azinobis 3-ethylbenzothiazoline-6-sulphonic bubbling of air and nitrogen has been successfully acid and 2, 6-dichloroindophenol as efficient used (Belkacemi and Hamoudi, 2010). Gold catalysts electron acceptors that can be regenerated by an have shown high stability against over oxidation additional enzyme, like laccase. Even though the and supported gold nanoparticles have shown an system produces lactobionic acid from lactose at a exceptional activity and selectivity in the oxidation high volumetricproductivity, the system is complex of carbohydrates (Belkacemi et al., 2007; Murzina et involving two enzymes and a redox mediator al., 2008; Gutiérrez et al., 2012). (Murakami et al., 2008; Van Hecke et al., 2009). EXTRACTION AND PURIFICATION In an industrial context, an enzymatic mixture called ‘LactoYIELD’ was launched onto the market in 2009 In order to achieve a higher productivity of lactobionic as a result of the joint venture in between the Danish acid, the enzymatic reaction can be interrupted after companies and Novozymes A/S in 2002 (Novozymes, few hours of operation and unreacted substrates can 2009). This standardized enzymatic mixture allows be recycled after the separation of substrates from cheese manufacturers to convert lactose from cheese products (Silveira, 2003). Liquid chromatography whey into lactobionic acid. is a high efficiency separation technique that could be useful in the current process since species can be Electrochemical oxidation recovered with high-purity (Pedruzzi et al., 2008). Lactobionic acid has been also prepared by By passing the solution of lactobionate ions through electrolytic oxidation processes. The studies carried a series of ion-exchange resins, a batch of pure out by Gutiérrez et al., (2012) reported that high yields lactobionic acid solution with negligible amounts (>90%) and selectivities (~100%) toward lactobionic of calcium ions can be produced. Other techniques acid can be obtained by means of the electro-catalytic like ethanol precipitation (Armarego and Chai, 2009), oxidation of lactose on noble metal electrodes evaporation and crystallization(Jones et al., 2002) and (platinum, platinum-modified and gold electrodes) in electrodialysis are also employed
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