Laura Alessandrini

Biocatalytic production of flavors and fragrances

The preparation of flavors and fragrances has to be done with great care. When these compounds are meant for consumption, no toxic chemicals are allowed during their preparation. For use in non-food additives, a high purity is required. Both constraints can be easily fulfilled when enzymes are used as catalyst during the production of these compounds. This paper summarizes the work that we have done regarding the preparation of branched-chain fatty acids (sheep flavors) using lipases, the production of glucosides (controlled-release flavors) using glucosidases, the formation of terpene alcohols and grapefruit flavor using enzymes from chicory, and the formation of phenolic antioxidants using lipases.

Clemmensen reduction of diosgenin and kryptogenin: synthesis of [16,16,22,22,23,23-2H6]-(25R)-26-hydroxycholesterol

A new experimental protocol has been established for the Clemmensen reduction of diosgenin and kryptogenin with the aim to prepare deuterated isotopomers of (25R)-26-hydroxycholesterol. Uncontrolled deuteration has been achieved from diosgenin, whereas [16,16,22,22,23,23-(2)H(6)]-(25R)-26-hydroxycholesterol (1) can be synthesized from kryptogenin.

Anisotropic optical functions of α-1,4,4-tetraphenyl-1,3-butadiene

One of the known monoclinic polymorphs of 1,1,4,4-tetraphenyl-1,3-butadiene was grown by the floating-drop technique. This material is of interest for blue emitting devices and for fundamental studies on intermolecular interactions, excited states and vibronic coupling in the fields of chemical physics and materials science. Polarized UV-visible spectra are reported. The origin of the optical bands is resolved. The results give information on the intermolecular interactions and are compared with theoretical predictions and modeling. The full material dielectric tensor is provided, as deduced from generalized spectroscopic ellipsometry. Details on the use of this technique on strongly anisotropic and absorbing molecular materials are given. Some typical features of the optical spectra are also demonstrated to be very sensitive to the presence of misaligned domains, which, in our samples, are found to be rotated around the normal to the surface and whose amount is determined. The method allows discriminating among monocrystals, in-plane polycrystalline samples, layered samples formed by misaligned successive layers, or samples with both types of disorder. Two independent parameters giving the fraction of misaligned domains or layers are suggested for the characterization and optimization of the growth and deposition of molecular organic materials.

Synthesis of Differently Protected 1‐C‐Methyl‐Ribofuranoses Intermediates for the Preparation of Biologically Active 1′‐C‐Methyl‐Ribonucleosides

Starting from D‐ribose, differently protected 1‐C‐methyl‐D‐ribofuranoses have been prepared as intermediates for the synthesis of variously modified 1′‐C‐methyl‐ribonucleosides, a class of compounds potentially endowed with interesting biological activity.

Synthesis of deuterated isotopomers of 7α- and (25R,S)-26-hydroxycholesterol, internal standards for in vivo determination of the two biosynthetic pathways of bile acids

Deuterated isotopomers of 7alpha- and (25R,S)-26-hydroxycholesterol, internal standards for in vivo determination of the two biosynthetic pathways of bile acids formation from cholesterol, were prepared from [2,2,3,4,4,6-2H(6)]-cholesterol and (20S)-[7,7,21,21-2H(4)]-3beta-(tert-butyldimethylsilyl)oxy-20-methylpregna-5-en-21-ol, respectively.

Deamination of 2′,3′-O-Isopropylideneadenosine-5′- Carboxylic Acid Catalyzed by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA): Influence of Substrate Ionization on the Activity of the Enzymes

Adenosine deaminase (ADA) and adenylate deaminase (AMPDA) catalyze the deamination of 2 ′,3 ′-O-isopropylideneadenosine-5′-carboxylic acid to the corresponding inosine derivative and dependence of the rate of enzymatic reaction on the ionization degree of the substrate has been studied at different pH values.

2′,3′-Isopropylidene Group, A Molecular Scaffold to Study the Activity of Adenosine and Adenylate Deaminase on Adenosine Analogues Modified in the Ribose Moiety

2 ′,3 ′-Isopropylidene group can be used as a molecular scaffold for the introduction of modifications at 5 ′ and 1 ′ positions of adenosine and these modified nucleosides are used to evaluate the biocatalytic activity of adenosine and adenylate deaminase.