Industrial kinetic resolution of <scp>d</scp>,<scp>l</scp>-pantolactone by an immobilized whole-cell biocatalyst

Zhang, Qiu-Hua; Liu, Yang; Tang, Yibin; Huang, Liu-Nv; Luo, Wen-Fang

doi:10.1039/d1ra05708a

Cited by 4 publications

(3 citation statements)

References 13 publications

(17 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pantolactone is an impurity (~1%) of panthenol raw materials, and because it is likely formed from panthenol in acidic aquatic media (i.e., sweat), it might not be excluded that this here newly reported cosmetic allergen is the actual sensitizer in panthenol‐containing preparations (Figure 2). 5,6 A possible argument in this direction is that pantolactone was also the strongest reactor in our two patients. Our cases once again highlight the utmost importance of identifying new emerging allergens through testing individual ingredients from all personal products used.…”

Section: Discussionmentioning

confidence: 85%

Allergic contact dermatitis from pantolactone and dexpanthenol in wound healing creams

et al. 2022

View full text Add to dashboard Cite

Section: Discussionmentioning

confidence: 85%

Allergic contact dermatitis from pantolactone and dexpanthenol in wound healing creams

et al. 2022

View full text Add to dashboard Cite

“…However, the recombinant Escherichia coli (TSDL) lacked sufficient stability, and its catalytic activity decreased when employed over repeated reactions. To resolve this issue, immobilized whole cells of Pichia pastoris harboring the recombinant D‐lactonase were entrapped in calcium alginate gels and used as biocatalysts for the catalytic kinetic resolution of DL‐PL [22] . The immobilized whole‐cell biocatalyst exhibited a high catalytic stability and was successfully applied in the stereospecific hydrolysis of D‐PL in 56 repeated batch reactions without any observable loss in catalytic activity or enantioselectivity, ultimately providing a practical route for the biocatalytic production of D‐PL.…”

Section: Resolution Of Dl‐plmentioning

confidence: 99%

Asymmetric Synthesis of Pantolactone: Recent Advances

Du,

Lv,

Liu

et al. 2023

Eur J Org Chem

View full text Add to dashboard Cite

(R)‐Pantolactone, an intermediate in the syntheses of Vitamin B5 and coenzyme A, is an important chiral molecule often used as a food additive, chiral auxiliary, and chiral starting material for organic transformations. Enantioenriched pantolactones are predominantly produced by biological fermentation and chemical synthesis approaches. Herein, we present a review of recent developments in the asymmetric synthesis of pantolactone via different methods, and systematically summarize the characteristics and advantageous features of these strategies. Among the strategies discussed herein, the direct asymmetric catalysis of glyoxylate and isobutyraldehyde with small organocatalyst molecules has attracted growing attention owing to its good step‐economy, commercially available starting materials, absence of toxic reagents, mild reaction conditions, convenient operation, and low catalyst loading. These characteristics render the direct asymmetric route to pantolactone a particularly attractive procedure. This review provides valuable guidance for the design and synthesis of enantioenriched pantolactone and its analogs.

show abstract

“…As a chiral alcohol, d -pantolactone serves as an important intermediate in the synthesis of d -pantothenic acid (vitamin B 5 ), which is widely used as a pharmaceutical and cosmetic ingredient as well as a food and feed additive [ 1 , 2 ]. In commercial production, d -pantothenic acid is synthesized through the condensation reaction between d -pantolactone and β-alanine, and d -pantolactone is mainly prepared through the lactonase-catalyzed resolution of racemic dl -pantolactone [ 3 , 4 , 5 , 6 ]. In the process of enzymatic resolution, the generated enantiopure d- pantothenic acid is separated from the remaining l -pantolactone and further converted into d- pantolactone by a chemical lactonization step, requiring the consumption of energy, solvents, and acids/alkalis [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Multi-Enzymatic Cascade for Efficient Deracemization of dl-Pantolactone into d-Pantolactone

et al. 2023

View full text Add to dashboard Cite

d-pantolactone is an intermediate in the synthesis of d-pantothenic acid, which is known as vitamin B5. The commercial synthesis of d-pantolactone is carried out through the selective resolution of dl-pantolactone catalyzed by lactone hydrolase. In contrast to a kinetic resolution approach, the deracemization of dl-pantolactone is a simpler, greener, and more sustainable way to obtain d-pantolactone with high optical purity. Herein, an efficient three-enzyme cascade was developed for the deracemization of dl-pantolactone, using l-pantolactone dehydrogenase from Amycolatopsis methanolica (AmeLPLDH), conjugated polyketone reductase from Zygosaccharomyces parabailii (ZpaCPR), and glucose dehydrogenase from Bacillus subtilis (BsGDH). The AmeLPLDH was used to catalyze the dehydrogenated l-pantolactone into ketopantolactone; the ZpaCPR was used to further catalyze the ketopantolactone into d-pantolactone; and glucose dehydrogenase together with glucose fulfilled the function of coenzyme regeneration. All three enzymes were co-expressed in E. coli strain BL21(DE3), which served as the whole-cell biocatalyst. Under optimized conditions, 36 h deracemization of 1.25 M dl-pantolactone d-pantolactone led to an e.e.p value of 98.6%, corresponding to productivity of 107.7 g/(l·d).

show abstract

Industrial kinetic resolution of d,l-pantolactone by an immobilized whole-cell biocatalyst

Abstract: Immobilized whole-cells of Pichia pastoris harboring recombinant d-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution of d,l-pantolactone.

Cited by 4 publications

References 13 publications

Allergic contact dermatitis from pantolactone and dexpanthenol in wound healing creams

Allergic contact dermatitis from pantolactone and dexpanthenol in wound healing creams

Asymmetric Synthesis of Pantolactone: Recent Advances

Multi-Enzymatic Cascade for Efficient Deracemization of dl-Pantolactone into d-Pantolactone

Contact Info

Product

Resources

About