Production of Various Phosphatidylsaccharides by Phospholipase D from<i>Actinomadura</i>sp. Strain No. 362

Kokusho, Yoshitaka; Tsunoda, Akira; Kato, Shigeaki; Machida, Haruo; Iwasaki, Shinsuke

doi:10.1271/bbb.57.1302

Cited by 27 publications

(9 citation statements)

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“…The rPLD103 produced both PG and PS from soybean lecithin. The transphosphatidylation reaction of PLD may enable to synthesize various phosphatidyl derivatives of hydroxyl compounds, such as phenols, sugars, nucleotides, vitamins, and others, in addition to glycerol and L-serine [34][35][36][37][38]. Phosphatidyl derivatives may improve the functioning of ingredients found in food supplements due to their emulsification properties, antioxidant abilities, and liposome formation abilities.…”

Section: Discussionmentioning

confidence: 99%

Large-Scale Production of Phospholipase D from Streptomyces racemochromogenes and Its Application to Soybean Lecithin Modification

Nakazawa

Sagane

Sakurai

et al. 2011

Appl Biochem Biotechnol

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Phospholipase D (PLD) catalyzes transphosphatidylation, causing inter-conversion of the polar head group of phospholipids and phospholipid hydrolysis. Previously, we cloned PLD103, a PLD with high transphosphatidylation activity, from Streptomyces racemochromogenes strain 10-3. Here, we report the construction of an expression system for the PLD103 gene using Streptomyces lividans as the host bacterium to achieve large-scale production. The phosphatidylcholine (PC) hydrolysis activity of S. lividans transformed with the expression plasmid containing the PLD103 gene was approximately 90-fold higher than that of the original strain. The recombinant PLD103 (rPLD103) found in the supernatant of the transformant culture medium was close to homogeneous. The rPLD103 was indistinguishable from the native enzyme in molecular mass and enzymatic properties. Additionally, rPLD103 had high transphosphatidylation activity on PC as a substrate in a simple aqueous one-phase reaction system and was able to modify the phospholipid content of soybean lecithin. Consequently, the expression system produces a stable supply of PLD, which can then be used in the production of phosphatidyl derivatives from lecithin.

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Section: Discussionmentioning

confidence: 99%

Large-Scale Production of Phospholipase D from Streptomyces racemochromogenes and Its Application to Soybean Lecithin Modification

Nakazawa

Sagane

Sakurai

et al. 2011

Appl Biochem Biotechnol

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“…The PLD-mediated transphosphatidylation was reported to be extended through synthesis of Ptdcho with unnatural polar head groups (Arranz-Martínez, Casado, Reglero, & Torres, 2017;Damnjanović & Iwasaki, 2013;Kokusho, Tsunoda, Kato, Machida, & Iwasaki, 1993;Song et al, 2012). It is a nontoxic carrier of bioactive compounds, due to the biocompatibility of the phosphatidyl moiety itself (Damnjanović & Iwasaki, 2013;Konagai et al, 2013).…”

Section: Discussionmentioning

confidence: 99%

Reaction Specificity of Phospholipase D Prepared from Acinetobacter radioresistens a2 in Transphosphatidylation

Cao

Liu

Tian

et al. 2018

Lipids

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Phospholipase D (PLD) can react with phospholipids as substrates, generally phosphatidylcholine (PtdCho), and the PLD-substrate intermediate can be cleaved by another alcohol, resulting in transphosphatidylation of the substrate, which can be used in the production of special lipids. In this study, the reaction conditions affecting the transphosphatidylation of PtdCho with serine were optimized and the reaction specificity of a novel PLD prepared from Acinetobacter radioresistens a2 was evaluated for transphosphatidylation with a variety of phospholipid substrates and head group donors. Based on the yield of phosphatidylserine, experimental kinetic data, maximum transphosphatidylation rate, and kinetic constant, the specificity of PLD in transphosphatidylation was found to be affected by unsaturated fatty-acid phospholipid substrates. The catalytic efficiency of PLD prepared from A. radioresistens a2 on the synthesis of natural phospholipids is on the order of l-serine > ethanolamine and glycerol ≫ inositol. Moreover, it was found that the transphosphatidylation of PtdCho with saccharides was related to the length of the carbon chain and the number of saccharide units.

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“…Therefore, it is promising to synthesize 1‐PGlc from PC and glucose by means of the PLD‐mediated transphosphatidylation. Indeed, several reports exist on synthesis of “phosphatidylglucose” by the PLD‐mediated reaction from PC and glucose However, the product reported in the literature is 6‐phosphatidylglucose (6‐PGlc), a positional isomer of 1‐PGlc .…”

Section: Methodsmentioning

confidence: 99%

Direct Enzymatic Synthesis of 1‐Phosphatidyl‐β‐D‐glucose by Engineered Phospholipase D

et al. 2016

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A simple, direct method for the synthesis of 1-phosphatidyl-b-D-glucose (1-PGlc) was established, being the first example of direct enzymatic synthesis of this recently discovered, highly important bioactive phospholipid. The method employs phospholipase D (PLD, E.C. 3.1.4.4)-catalyzed transphosphatidylation, in which the polar head group of phosphatidylcholine is exchanged to glucose. Although wild-type PLD can catalyze the transfer reaction, it provides only 6-phosphatidyl-glucose, a positional isomer of 1-PGlc, due to its strong preference towards the primary hydroxyl group. To synthesize 1-PGlc, engineered PLD variants, previously isolated as the ones active on secondary hydroxyls of inositol, were screened for the ability to catalyze the reaction. One of the variants, 187K/191W/385Y (KWY), was identified as the best-performing in 1-PGlc synthesis, however, in addition to 1-PGlc the reaction with KWY also afforded undesired positional isomers as byproducts. To facilitate the isolation of 1-PGlc, the isomers were converted into the corresponding amines by reductive amination. Following the column chromatography, the desired product was isolated with the overall yield of 12.5 %. The structure of the product was confirmed by 1 H-NMR analysis.

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Production of Various Phosphatidylsaccharides by Phospholipase D fromActinomadurasp. Strain No. 362

Cited by 27 publications

References 0 publications

Large-Scale Production of Phospholipase D from Streptomyces racemochromogenes and Its Application to Soybean Lecithin Modification

Large-Scale Production of Phospholipase D from Streptomyces racemochromogenes and Its Application to Soybean Lecithin Modification

Reaction Specificity of Phospholipase D Prepared from Acinetobacter radioresistens a2 in Transphosphatidylation

Direct Enzymatic Synthesis of 1‐Phosphatidyl‐β‐D‐glucose by Engineered Phospholipase D

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