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Synthetic method of hydroxypropyl tetrahydropyrantriol catalyzed by biological enzyme

A technology of hydroxypropyltetrahydropyrantriol and acetone-based tetrahydropyrantriol is applied in the synthesis field of cosmetic active substance hydroxypropyltetrahydropyrantriol, and can solve the problem of low stereoselectivity and environmental problems. Serious pollution, potential safety hazards and other problems, to achieve the effects of high purity, high enzyme conversion rate, and no metal residues

Pending Publication Date: 2021-09-21
SHANGHAI COACHCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are some following problems in these conventional chemical reduction reactions: stereoselectivity is not high; Three wastes discharge is higher, and environmental pollution is serious; Some reagents are relatively expensive; Some reactions need high-pressure hydrogen, and there are potential safety hazards, etc.
It is particularly worth mentioning that some reactions catalyzed by transition metals will have metal residues in the product, which is especially unfavorable for pharmaceutical and cosmetic active substances

Method used

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  • Synthetic method of hydroxypropyl tetrahydropyrantriol catalyzed by biological enzyme
  • Synthetic method of hydroxypropyl tetrahydropyrantriol catalyzed by biological enzyme
  • Synthetic method of hydroxypropyl tetrahydropyrantriol catalyzed by biological enzyme

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1 (medium and reagent configuration)

[0015] (1) Luria-Bertani (LB) medium: Tryptone 10g L -1 , Yeast extract 5g·L -1 , NaCl 10 g·L -1 , Agarose 20g·L -1 (for solid medium), 5.0mol·L -1 Adjust the pH to 7.0 with NaOH (approximately 1‰) and sterilize at 121°C for 20min.

[0016] (2) 50mg·mL -1 Ampicillin solution (Amp): Dissolve 1 g of ampicillin in 20 mL of sterilized deionized water, filter and sterilize with a 0.22 μm filter membrane (Agela), dispense into sterile eppendorf tubes, 1 mL each, and store at -20°C for later use. Before use, add an amount of 1‰, that is, the final concentration is 50μg·mL -1 .

[0017] (3) 50mg·mL -1 Kanamycin Solution (Kan): Dissolve 1g Kanamycin in 20mL sterile deionized water, filter and sterilize with a 0.22μm filter membrane (Agela), dispense into sterile eppendorf tubes, 1mL each, -20°C Save for later. Before use, add an amount of 1‰, that is, the final concentration is 50μg·mL -1 .

[0018] (4) 200mg·mL -1 I...

Embodiment 2

[0030] Embodiment 2 (amplification of target gene)

[0031] The primers required for the PCR of aldehyde and ketone reductase AKR and alcohol dehydrogenase ADH were designed, and NdeI and XhoI restriction sites were respectively inserted at the carbon and nitrogen ends of the target gene by PCR.

[0032] Primer design

[0033]

[0034] Design primers and perform PCR operation. During PCR operation, a total reaction system of 50 μL is used. The system composition is as follows

[0035]

[0036] PCR conditions: ①Pre-denaturation at 98°C, 2min;

[0037] ② Denaturation at 98°C, 10s; annealing at 58°C, 5s; extension at 72°C, 5s / kb; cycle 35 times;

[0038] ③ Extend at 72°C for 5 minutes;

[0039] ④ 4°C, 1h (PCR can be terminated at any time at this stage).

Embodiment 3

[0040] Embodiment 3 (construction of pET-28a (+)-adh and pET-28a (+)-akr recombinant plasmid)

[0041] After the PCR product (ADH gene and AKR gene) was digested with double enzymes (NdeII and XhoI), it was ligated with the same double digested plasmid pET-28a(+) at 22°C for 2 hours; Transformed into E.coli DH5α competent, after sequencing and identification, the recombinant plasmids were then transferred into E.coli BL21(DE3), and the recombinant plasmids were named pET-28a(+)-adh and pET-28a(+)-akr , and then stored in a -80°C refrigerator.

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Abstract

The invention belongs to the field of organic synthesis, fine chemicals and daily chemicals, and particularly relates to a synthetic method of hydroxypropyl tetrahydropyrantriol catalyzed by a biological enzyme. According to the method, a double-enzyme circulating catalysis system containing aldoketo reductase (AKR) and ethanol dehydrogenase (ADH) is used, and in the presence of oxidized coenzyme II (NADP), isopropanol is used as a reducing agent, so that the synthesis of the hydroxypropyl tetrahydropyrantriol is realized. As biological enzyme catalysis is adopted, the method is mild in condition, simple and convenient to operate, small in pollution, green, safe, free of metal residues and high in product purity, and is particularly suitable for synthesis of active matters of medicines and cosmetics.

Description

technical field [0001] The invention belongs to the fields of organic synthesis, fine chemicals and daily chemicals, and in particular relates to a method for synthesizing hydroxypropyltetrahydropyrantriol, a cosmetic active substance catalyzed by biological enzymes. Background technique [0002] Hydroxypropyltetrahydropyranotriol (CAS No. 439685-79-7) is a biologically active substance that can fight against skin aging, dehydration and other symptoms, and is widely used in food, biology, medicine, cosmetics and many other fields. For the synthesis method of hydroxypropyltetrahydropyrantriol, the currently published literature is mainly realized by the reduction of acetonyl tetrahydropyrantriol (CAS No. 439685-73-1) (the following formula). Among them, the main reduction conditions include sodium borohydride reduction and transition metal catalyzed hydrogenation reaction. There are some following problems in these conventional chemical reduction reactions: stereoselectivity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/06C12N9/04C12N15/53
CPCC12P17/06C12N9/0006C12Y101/01001C12Y101/01002
Inventor 吴江张伟朱纯银周宝萍
Owner SHANGHAI COACHCHEM TECH
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