Microbially Produced Functionalized Cyclohexadiene‐
            <i>Trans</i>
            ‐Diols As a New Class of Chiral Building Block in Organic Synthesis: On the Way to Green and Combinatorial Chemistry

Lorbach, Volker; Franke, Dirk; Esser, Simon; Dose, Christian; Sprenger, Georg A.; Müller, Michael

doi:10.1002/3527603727.ch6d

Cited by 4 publications

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“…34 The shikimate pathway is an instructive example of diversity-oriented biosynthesis of a wide spectrum of natural products (Scheme 1). 35,36 Shikimate-and chorismate-derived metabolites and their enzymatic transformations have been applied in synthesis, notably by Frost et al 37 and by Müller et al [38][39][40][41][42] These multifunctionalized and conformationally restricted natural products could serve as valuable chiral auxiliaries, chiral ligands, and organocatalysts in asymmetric transformations. Here, we focus on the production of the microbial nonproteinogenic amino acids 2,3-trans-CHA and 3,4-trans-CHA (4), and derivatives thereof, and their use as potent (organo)catalysts.…”

Section: Introductionmentioning

confidence: 99%

β- and σ-Amino acids (2,3- and 3,4-trans-CHA) as catalysts in Knoevenagel condensation and asymmetric aldol reactions

Al-Momani¹,

Lorbach²,

Detry³

et al. 2017

Arkivoc

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The efficacy of the β-and δ-amino acids (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-dienecarboxylic acid (2,3-trans-CHA) and (3R,4R)-4-amino-3-hydroxycyclohexa-1,5-dienecarboxylic acid (3,4-trans-CHA) as catalysts in Knoevenagel condensation and aldol addition reactions is studied. Synthesis of the zinc(II) complexes of 2,3-and 3,4-trans-CHA provided precipitated material of sufficient purity for use. The catalytic Knoevenagel reactions were carried out with the β-amino acid 2,3-trans-CHA and the δ-amino acid 3,4-trans-CHA, resulting in a product yield of up to 61%. The asymmetric aldol addition reactions were carried out with catalytic amounts of the zinc(II) complexes of 2,3-and 3,4-trans-CHA. In this case, it was observed that the ee of the product (up to 90%) depends on the conversion and/or the reaction time.

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Section: Introductionmentioning

confidence: 99%

β- and σ-Amino acids (2,3- and 3,4-trans-CHA) as catalysts in Knoevenagel condensation and asymmetric aldol reactions

Al-Momani¹,

Lorbach²,

Detry³

et al. 2017

Arkivoc

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Cyclohexa‐3,5‐diene‐1,2‐trans‐diols – Synthesis and Application in Target‐Oriented Syntheses

2012

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An exhaustive overview of the field of cyclohexa‐3,5‐diene‐1,2‐trans‐diols is given. Early and recent methods for the formation of the compounds are reviewed and the various syntheses in which the title compounds have been applied are presented. Special emphasis is given to naturally occurring epoxides, which have been the dominant target molecules since the 1970s. Finally, recent advances in biotechnology are highlighted; with the increased availability of the enantiomerically pure cyclohexa‐3,5‐diene‐1,2‐trans‐diols, new synthetic endeavours were initiated.

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Biochemical reaction engineering for redox reactions

Wandrey

2004

The Chemical Record

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Redox reactions are still a challenge for biochemical engineers. A personal view for the development of this field is given. Cofactor regeneration was an obstacle for quite some time. The first technical breakthrough was achieved with the system formate/formate dehydrogenase for the regeneration of NADH2. In cases where the same enzyme could be used for chiral reduction as well as for cofactor regeneration, isopropanol as a hydrogen source proved to be beneficial. The coproduct (acetone) can be removed by pervaporation. Whole-cell reductions (often yeast reductions) can also be used. By proper biochemical reaction engineering, it is possible to apply these systems in a continuous way. By cloning a formate dehydrogenase and an oxidoreductase "designer bug" can be obtained where formate is used instead of glucose as the hydrogen source. Complex sequences of redox reactions can be established by pathway engineering with a focus on gene overexpression or with a focus on establishing non-natural pathways. The success of pathway engineering can be controlled by measuring cytosolic metabolite concentrations. The optimal exploitation of such systems calls for the integrated cooperation of classical and molecular biochemical engineering.

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Microbially Produced Functionalized Cyclohexadiene‐ Trans ‐Diols As a New Class of Chiral Building Block in Organic Synthesis: On the Way to Green and Combinatorial Chemistry

Cited by 4 publications

References 0 publications

β- and σ-Amino acids (2,3- and 3,4-trans-CHA) as catalysts in Knoevenagel condensation and asymmetric aldol reactions

β- and σ-Amino acids (2,3- and 3,4-trans-CHA) as catalysts in Knoevenagel condensation and asymmetric aldol reactions

Cyclohexa‐3,5‐diene‐1,2‐trans‐diols – Synthesis and Application in Target‐Oriented Syntheses

Biochemical reaction engineering for redox reactions

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