[Show abstract][Hide abstract] ABSTRACT: The title mol-ecule, CHO, is composed of three six-membered rings (//) and a five-membered ring (). Ring adopts a 1α-sofa conformation, while rings and adopt chair conformations. Cyclo-pentane ring adopts a 14α-envelope conformation. In the crystal, O-H⋯O hydrogen bonds lead to the formation of ribbons running along the axis. The structure is further consolidated by C-H⋯O inter-actions, which link the molecules head-to-tail into ribbons along the axis.
[Show abstract][Hide abstract] ABSTRACT: Cyclodextrins (CDs) can improve productivity in the biotransformation of steroids by increasing conversion rate, conversion ratio, or substrate concentration. However, little is known of the proportion of products formed by multi-catabolic enzymes, e.g., via sterol side chain cleavage. Using three strains with different androst-1,4-diene-3,17-dione (ADD) to androst-4-ene-3,17-dione (AD) ratios, Mycobacterium neoaurum TCCC 11028 (MNR), M. neoaurum TCCC 11028 M1 (MNR M1), and M. neoaurum TCCC 11028 M3 (MNR M3), we found that hydroxypropyl-β-cyclodextrin (HP-β-CD) can appreciably increase the ratio of ADD to AD, the reaction rate, and the molar conversion. In the presence of HP-β-CD, conversion of 0.5 g/L of phytosterol (PS) was 2.4, 2.4, and 2.3 times higher in the MNR, MNR M1, and MNR M3 systems, respectively, than in the controls. The ADD proportion increased by 38.4, 61.5, and 5.9 % compared with the control experiment, which resulted in a strong shift in the ADD/AD ratio in the ADD direction. Our results imply that the three PS-biotransforming strains cause efficient side chain degradation of PS, and the increased conversion of PS when using HP-β-CD may be associated with the higher PS concentration in each case. A similar solubilizing effect may not induce a prominent influence on the ADD/AD ratio. However, the different activities of the Δ¹-dehydrogenase of PS-biotransforming strains result in different incremental percentage yields of ADD and ADD/AD ratio in the presence of HP-β-CD.
[Show abstract][Hide abstract] ABSTRACT: The title compound, C(19)H(26)O(4), was biotransformed from androstenedione. In the crystal, inter-molecular O-H⋯O hydrogen bonds link molecules into a corrugated sheet, which lies parallel to the ab plane. Ring A has a slightly distorted half-chair conformation, rings B and C adopt chair conformations, while the cyclo-pentane ring D adopts a 14α-envelope conformation.
[Show abstract][Hide abstract] ABSTRACT: An intensive and systematic investigation had been carried out on the Delta(1)-dehydrogenation of cortisone acetate (CA) to prednisone acetate (PA) by Arthrobacter simplex TCCC 11037 in the presence of native and modified beta-cyclodextrins (beta-CDs). The biotransformation was improved through the formation of the host-guest inclusion complex between CA and CDs in aqueous solution. The inclusion complexes of CDs with CA were investigated by means of phase solubility, 2D NMR spectroscopy and differential scanning calorimetry (DSC). The structural difference of CDs resulted in the stoichiometric differences between the complexes, the RM-beta-CD-CA, SBE-beta-CD-CA, HP-beta-CD-CA complexes were 1:1 whereas beta-CD-CA gave both 1:1 and 2:1 complexes, of which the 2:1 complex decreased the soluble CA concentration and inhibited the dissociation of beta-CD-CA in aqueous solution. The increase in solubility of CA was in the order of RM-beta-CD>SBE-beta-CD>HP-beta-CD>beta-CD. RM-beta-CD-CA, SBE-beta-CD-CA and HP-beta-CD-CA exhibited the higher biotransformation rate in comparison with native beta-CD. And the solubilization of CDs for CA in aqueous medium plays a key role in the biotransformation process. The article focuses on the various factors influencing the substrate water solubility, complex stability and biotransformation of CA through the addition of CDs in order to solve many problems associated with the process of drug delivery and biotransformation of different novel steroids.
The Journal of steroid biochemistry and molecular biology 09/2009; 117(4-5):146-51. DOI:10.1016/j.jsbmb.2009.08.007 · 3.63 Impact Factor