Synthesis of 6‐phosphatidyl‐L‐ascorbic acid by phospholipase D

Nagao, Akihiko; Ishida, Noriko; Terao, Junji

doi:10.1007/bf02537205

Cited by 42 publications

(19 citation statements)

References 30 publications

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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: 98%

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: 98%

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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“…8, compound 1) [54]. It was revealed that PAsA suppressed oxidation of PC in multilamelar liposomes [55].…”

Section: Synthesis Of Pls Containing Bio-active Compoundsmentioning

confidence: 99%

Enzymatic Synthesis of Structured Lipids

Iwasaki

Yamané

2004

Recent Progress of Biochemical and Biomedical Engineering in Japan I

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“…Phosphatidyl genipin 15 and phosphatidyl arbutin 16 incorporate large bioactive molecules from natural sources [147,148]. The idea of preparing PL bearing a pharmacologically active molecule in the polar head has produced a number of new molecules including phosphatidyl nucleotides 17 proposed as antivirals [18], phosphatidyl ascorbic acid 19 for its antioxidant activity [149], or a phospholipid 20 containing a modified sialic acid moiety as an enzyme inhibitor [17]. Compound 18 has also been prepared using PLD from Streptomyces as a biocatalyst in good yield [150].…”

Section: Transfer To Primary Alcoholsmentioning

confidence: 99%

Phospholipases as Synthetic Catalysts

Servi

1999

Topics in Current Chemistry

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Natural phospholipids can be completely modified with a group of hydrolytic enzymes found in living organisms. Phospholipase A 1 , phospholipase A 2 , and 1,3-specific lipases are hydrolases which can selectively cleave the ester bonds at position sn1 and sn2. The compounds of partial hydrolysis can be reacylated chemically. Each of the compounds obtained can then be modified with the very efficient phospholipase D which can effect polar head substitution in the presence of an alcohol as a phosphoryl acceptor. The enzymes from bacterial sources are readily available from culture broth and are highly selective. Phospholipase C can be used to obtain diacylglycerol and organic phosphates as hydrolysis products. The sequential use of the latter enzymes allows the preparation of organic diphosphates. The factors affecting the specificity and selectivity of these enzymes is discussed.

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Synthesis of 6‐phosphatidyl‐L‐ascorbic acid by phospholipase D

Cited by 42 publications

References 30 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

Enzymatic Synthesis of Structured Lipids

Phospholipases as Synthetic Catalysts

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