D-(-)-Pantolactone
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| Category | Others |
| Catalog number | BBF-05248 |
| CAS | 599-04-2 |
| Molecular Weight | 130.14 |
| Molecular Formula | C6H10O3 |
| Purity | ≥ 95 % |
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Description
D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions. It is also an important intermediate in the synthesis of pantothenic acid and a degradation product of pantothneic acid in the liver.
Specification
| Related CAS | 5405-40-3 (S-configuration) |
| Synonyms | (3R)-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone; (-)-(R)-Pantolactone; (-)-2-Hydroxy-3,3-dimethyl-γ-butyrolactone; (-)-Pantoyl Lactone; (3R)-Tetrahydro-3-hydroxy-4,4-dimethylfuran-2-one; Pantothenic Lactone; D-(-)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; (R)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; Pantolactone; (R)-pantolactone; (R)-3-hydroxy-4,4-dimethyldihydrofuran-2(3H)-one |
| Storage | Store at 2-8 °C under inert atmosphere |
| IUPAC Name | (3R)-3-hydroxy-4,4-dimethyloxolan-2-one |
| Canonical SMILES | CC1(COC(=O)C1O)C |
| InChI | InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1 |
| InChI Key | SERHXTVXHNVDKA-BYPYZUCNSA-N |
Properties
| Appearance | White to off-white solid |
| Boiling Point | 120-122 °C at 15 mmHg |
| Melting Point | 88-92 °C |
| Flash Point | 99°C |
| Density | 1.165 g/cm3 |
| Solubility | Sparingly soluble in Chloroform, Methanol; Slightly soluble in Ethyl Acetate, Water |
| LogP | -0.06970 |
Reference Reading
1. Industrial kinetic resolution of d,l-pantolactone by an immobilized whole-cell biocatalyst
Qiu-Hua Zhang, Liu Yang, Yi-Bin Tang, Liu-Nv Huang, Wen-Fang Luo RSC Adv. 2021 Sep 13;11(48):30373-30376. doi: 10.1039/d1ra05708a. eCollection 2021 Sep 6.
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. The immobilized whole-cell biocatalyst exhibited good catalytic stability, which was applied for stereospecific hydrolysis of d-pantolactone for up to 56 repeated batch reactions without obvious loss in the catalytic activity and enantioselectivity.
2. Biocatalytic kinetic resolution of d,l-pantolactone by using a novel recombinant d-lactonase
Qiu-Hua Zhang, Yi Fang, Wen-Fang Luo, Liu-Nv Huang RSC Adv. 2020 Dec 24;11(2):721-725. doi: 10.1039/d0ra09053k.
d-Pantolactone is a key chiral intermediate for the synthesis of d-pantothenic acid and its derivatives. Biocatalytic kinetic resolution of d,l-pantoyl lactone using d-lactonase is an efficient route to synthesize d-pantolactone. In this study, we report the expression of a novel d-lactonase TSDL in Escherichia coli host. The recombinant TSDL exhibited high hydrolysis activity and enantioselectivity toward d-pantolactone. The reaction conditions of the recombinant TSDL-catalyzed kinetic resolution of d,l-pantolactone was systematically investigated by whole cell biocatalysis. In addition, a preparative-scale reaction for bioproduction of d-pantoic acid was examined under optimized reaction conditions. This study presented an alternative enzymatic process for kinetic resolution of d,l-pantolactone.
3. Biocatalysis of heterogenously-expressed d-lactonohydrolases and its efficient preparation of desirable d-pantoic acid
Ruobin Sun, Pu Zheng, Dan Wu, Pengcheng Chen, Yanbing Bai, Jun Wang Enzyme Microb Technol. 2022 Apr;155:109981. doi: 10.1016/j.enzmictec.2021.109981. Epub 2022 Jan 5.
d-Pantoic acid (D-PA) is an essential intermediate for the production of d-pantolactone. Here, three d-lactonohydrolases (D-Lacs), namely, Fm-Lac from Fusarium moniliforme SW-902, Fp-Lac from Fusarium proliferatum Nirenberg ECU2002, and Fo-Lac from Fusarium oxysporum AKU3702 were heterogeneously expressed in Pichia pastoris. The constructed recombinant strains produced D-Lacs of 1263 U/mL, 1025 U/mL, and 948 U/mL in a 3-L fermenter, respectively. Simultaneously, these three D-Lacs were used to resolve racemic pantolactone (DL-PL), the hydrolysis rate by Fo-Lac over 40% and the enantiomeric excesses was 99% after 4 h reaction, which outperformed Fm-Lac and Fp-Lac. Under the 800 mL scale reaction, the hydrolysis rate of DL-PL reached 39.2% with a D-PA concentration of 144.6 g/L and space-time yield of 36.2 g/L/h correspondingly. This is the highest catalytic efficiency reported so far, which shows that D-Lac heterologously expressed by P. pastoris has excellent industrial application prospects.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
