Stereoselective hydrolysis of racemic ethyl 4-chloro-3-hydroxybutyrate by a lipase

Chung, Sunho; Hwang, YuneSahng

doi:10.1080/10242420801897585

Cited by 2 publications

(1 citation statement)

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“…In fact, opening of (S)-32 with HBr/EtOH will yield the corresponding ethyl (S)-4-bromo-3-hydroxybutanoate ((S)-BHBE, (S)-33) [179], later transformed into HN via S N 2 when treated with sodium (or potassium) bromide. Although (S)-32 can be produced from chiral pool raw materials (lactose or malic acid), it can be conveniently obtained by enzymatic hydrolysis of the racemic ethyl 4-chloro-3-hydroxybutanoate (CHBE, rac-29) in the aqueous phase [180]. The lipase stereoselectively hydrolysed only the (S)-enantiomer; however, the resulting acid (S)-30 is unstable, and it readily loses one HCl molecule to give the corresponding lactone of high enantiopurity (>99% ee).…”

Section: Hydrolases As Catalysts For the Preparation Of The Lateral Cmentioning

confidence: 99%

Biocatalyzed Synthesis of Statins: A Sustainable Strategy for the Preparation of Valuable Drugs

2019

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Statins, inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase, are the largest selling class of drugs prescribed for the pharmacological treatment of hypercholesterolemia and dyslipidaemia. Statins also possess other therapeutic effects, called pleiotropic, because the blockade of the conversion of HMG-CoA to (R)-mevalonate produces a concomitant inhibition of the biosynthesis of numerous isoprenoid metabolites (e.g., geranylgeranyl pyrophosphate (GGPP) or farnesyl pyrophosphate (FPP)). Thus, the prenylation of several cell signalling proteins (small GTPase family members: Ras, Rac, and Rho) is hampered, so that these molecular switches, controlling multiple pathways and cell functions (maintenance of cell shape, motility, factor secretion, differentiation, and proliferation) are regulated, leading to beneficial effects in cardiovascular health, regulation of the immune system, anti-inflammatory and immunosuppressive properties, prevention and treatment of sepsis, treatment of autoimmune diseases, osteoporosis, kidney and neurological disorders, or even in cancer therapy. Thus, there is a growing interest in developing more sustainable protocols for preparation of statins, and the introduction of biocatalyzed steps into the synthetic pathways is highly advantageous-synthetic routes are conducted under mild reaction conditions, at ambient temperature, and can use water as a reaction medium in many cases. Furthermore, their high selectivity avoids the need for functional group activation and protection/deprotection steps usually required in traditional organic synthesis. Therefore, biocatalysis provides shorter processes, produces less waste, and reduces manufacturing costs and environmental impact. In this review, we will comment on the pleiotropic effects of statins and will illustrate some biotransformations nowadays implemented for statin synthesis.

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Section: Hydrolases As Catalysts For the Preparation Of The Lateral Cmentioning

confidence: 99%