Steroids. XXXVIII. Synthesis of the acetate of Reichstein's substance S

Sokolova, L. V.; Klimova, L. I.; Kaminka, E. M.; Yaroslavtseva, Z. A.; Суворов, Н. Н.

doi:10.1007/bf00761020

Cited by 3 publications

(2 citation statements)

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“…The identity of the product was confirmed by its melting point, which was in accordance with reported data,11 and by spectroscopic methods. The acetylation on the hydroxy group of C‐21 was confirmed by observing the downfield shift in the 1 H NMR signals of the 21‐H resonance from = 4.28 and 4.56 ppm in substrate 1 to = 4.86 and 5.09 ppm in product 2 , respectively, and the appearance of a new signal corresponding to CH 3 ‐23 of the acetyl group at δ = 2.17 ppm.…”

Section: Resultssupporting

confidence: 89%

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Immobilized Heterologous Rhizopus Oryzae Lipase as an Efficient Catalyst in the Acetylation of Cortexolone

et al. 2012

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The enzymatic preparation of a monoacetyl derivative of the corticosteroid cortexolone, through a transesterification reaction, is described. The heterologous Rhizopus oryzae lipase, immobilized on three different supports, proved to be an efficient catalyst in the acylation reaction using a complex substrate such as cortexolone. Immobilization of the enzyme on Lewatit 1600 resin at pH = 7 and 25 °C was the best condition for catalysis of the acetylation reaction. The influence of various reaction parameters, such as the nature of the acetylating agent, the solvent, the temperature, and the ratios of acetylating agent to substrate, and enzyme to substrate, was evaluated. Using the response surface methodology and a central composite rotatable design, the specific yield of acetylated cortexolone was optimized by means of the study of the effect of the enzyme (E)/substrate (S) and the acylating agent (A)/substrate ratios. The ratios of 5 (E/S) and 31.6 (A/S) were predicted as the optimal values to reach the maximum specific yield of the product (P): 1.59 mmol P/mmol A·g E. The mild reaction conditions and low environmental impact make the biocatalytic procedure a convenient way to prepare the reported derivative of this biologically active steroid.

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Section: Resultssupporting

confidence: 89%

“…Regarding its synthesis, cortexolone‐21‐acetate was previously prepared from pregnenolone acetate in six steps 11. However, to obtain the 21‐monoester in a purity that was suitable for biological tests and pharmacological applications following this method, a complex and resource‐intensive purification procedure is necessary.…”

Section: Introductionmentioning

confidence: 99%