Sucrose phosphorylases catalyze transglycosylation reactions on carboxylic acid compounds

Sugimoto, Kazuhisa; Nomura, Koji; Nishiura, Hiromi; Ohdan, Kohji; Nishimura, Takahisa; Hayashi, Hideo; Kuriki, Takashi

doi:10.2478/s11756-008-0161-5

Cited by 6 publications

(2 citation statements)

References 19 publications

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“…In contrast to glycosyltransferases, extracellular glycosidases are readily available robust enzymes, operating under broad reaction conditions with much cheaper glycosyl donors. Glycosylation of carboxylic acids (e. g. benzoic acid) was described with sucrose phosphorylase from Streptococcus mutans ; here the products were only α‐glucopyranosides . Glycosylation of caffeic acid with recombinant sucrose phosphorylase from Bifidobacterium longum was demonstrated in supercritical CO 2 .…”

Section: Introductionmentioning

confidence: 95%

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

et al. 2019

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Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time-consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure-activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS. Scheme 2. Glycosylation of (E)-p-coumaric acid (3). Scheme 3. Proposed mechanism of rutinosylation of hydroxycinnamic acids at the carboxy moiety.

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Section: Introductionmentioning

confidence: 95%

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

et al. 2019

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“…Sucrose phosphorylase (SPase), primarily derived from Leuconostoc sp., was the first GT demonstrated to be capable of transferring phosphorylated glucose or glucose groups produced by sucrose decomposition to other receptors to produce α-arbutin ( Sugimoto et al, 2008 ). In 1994, the SPase of Leuconostoc mesenteroides was first demonstrated to be capable of catalyzing α-arbutin biosynthesis ( Kitao & Sekine, 1994 ).…”

Section: Arbutin Production Via Biotransformationmentioning

confidence: 99%

Recent Progress on Feasible Strategies for Arbutin Production

Xue

et al. 2022

Front. Bioeng. Biotechnol.

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Arbutin is a hydroquinone glucoside and a natural product present in various plants. Arbutin potently inhibits melanin formation. This property has been exploited in whitening cosmetics and pharmaceuticals. Arbutin production relies mainly on chemical synthesis. The multi-step and complicated process can compromise product purity. With the increasing awareness of sustainable development, the current research direction prioritizes environment-friendly, biobased arbutin production. In this review, current strategies for arbutin production are critically reviewed, with a focus on plant extraction, chemical synthesis, biotransformation, and microbial fermentation. Furthermore, the bottlenecks and perspectives for future direction on arbutin biosynthesis are discussed.

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