An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one

Abstract

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Structure and Bioassay of Triterpenoids and Steroids Isolated from Sinocalamus affinis

“…Alkaline hydrolysis of 7 liberated 7a, having 1 H NMR and EIMS data consistent with those of 20-hydroxypregn-4-en-3-one. 9 This revealed that 7 was 20-Omyristoylpregn-4-en-3-one, which was confirmed by the HMBC correlations of H 3 -21/C-17 and C-20 and H-20/C-1′. The ECD spectrum of 7 showed Cotton effects at 235 (Δε +5.78) and 322 (Δε −1.21) nm, corresponding to the π→π* and n→π* transitions of the conjugated 4-en-3-one chromophore, indicating that the tetracyclic nucleus of 7 possessed the same absolute configuration as the common pregn-4-en-3-one analogues on the basis of the octant rule.…”

“…F 3-6 (1.6 g) was repeatedly separated by CC over silica gel (petroleum ether−EtOAc, 50:1−3:1), followed by RP semipreparative HPLC (94% MeOH in H 2 O) purification to yield (E)-4-oxo-β-dihydroionone (1.8 mg), (3S,5R,6S)-3-acetoxy-5,6-epoxy-5,6-dihydro-β-ionone (1.5 mg), (22E)-ergosta- 6,9,22-triene-3β,5α,8α-triol (3.6 mg), and (22E)-ergosta-6,22-diene-3β,5α,8α-triol (5.0 mg). F 6 (21.0 g) was separated by flash chromatography over MCI gel, to give F 6-1 −F [6][7][8][9][10][11] . Separation of F 6-7 (3.6 g) by chromatography over Sephadex LH-20 (petroleum ether−CHCl 3 −MeOH, 2:2:1) and RP semipreparative HPLC (60% MeOH in H 2 O) yielded 1 (31.9 mg), 2 (1.8 mg), 3 (2.0 mg), 4 (4.1 mg), and 5 (3.4 mg).…”

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

“…In addition, in previous papers, we observed that, in androstanes and pregnanes, Candida rugosa lipase showed a preference for C‐3‐hydroxy or ‐acyloxy groups, whereas Candida antarctica catalyzed the reactions at the D‐ring 22. Taking into account these properties, we have prepared fatty acid derivatives of dehydroepiandrosterone,23 3,17‐β‐estradiol,24 and a series of novel 20‐succinates of pregnanes 25…”

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

“…[21][22][23][24][25]. In our laboratory several studies have been accomplished on the use of lipases, obtaining a wide variety of biologically active compounds, many of them new [26][27][28][29][30][31][32][33][34][35].…”