In this study, we present the synthesis of chiral fragrance aldehydes, which was tackled by a combination of chemo-catalysis and a multi-enzymatic in vivo cascade reaction and the development of a highly versatile high-throughput assay for the enzymatic reduction of carboxylic acids. We investigated a biocompatible metal-catalyzed synthesis for the preparation of α or β substituted cinnamic acid derivatives which were fed directly into the biocatalytic system. Subsequently, the target molecules were synthesized by an enzymatic cascade consisting of a carboxylate reduction, followed by the selective C-C double bond reduction catalyzed by appropriate enoate reductases. We investigated a biocompatible oxidative Heck protocol and combined it with cells expressing a carboxylic acid reductase from Neurospora crassa (NcCAR) and an ene reductase from Saccharomyces pastorianus for the production fragrance aldehydes.
myo-Inositol-2,3-D-camphor ketal crystallizes as an incommensurate structure with the C2(0σ2½) superspace group symmetry [σ2 = 0.1486 (3) at 100 K]. The bornane and myo-inositol moieties aggregate in distinct layers extending parallel to (001). The myo-inositol rings are connected by a complex hydrogen-bonding network extending in two dimensions, which is disordered in the basic structure and (mostly) ordered in the actual modulated structure. The domains of definition of the H atoms in internal space were derived by chemical reasoning and modeled with crenel functions. By tracing the hydrogen bonding, distinct chains, which are periodic in the [100] direction, are identified. These chains possess one of two possible orientations with respect to the hydrogen bonding. The incommensurate modulation is characterized by a non-periodic succession of the two chain orientations in the [010] direction. On heating, the σ2-component of the modulation wave vector decreases from σ2 = 0.1486 (3) at 100 K to σ2 = 0.1405 (6) at 430 K, which means that the periodicity of the modulation wave increases. No order–disorder phase transition was evidenced up to the melting point (with decomposition).
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