Flow synthesis of phenylserine using threonine aldolase immobilized on Eupergit support

• Jagdish D. Tibhe,
• Hui Fu,
• Timothy Noël,
• Qi Wang,
• Jan Meuldijk and
• Volker Hessel

Beilstein J. Org. Chem. 2013, 9, 2168–2179, doi:10.3762/bjoc.9.254

• , there is indication that biocatalysis under flow conditions provided by a microreactor can result in better process control by external numbering-up in which each subunit of reaction can be examined separately with enhanced productivity [11]. Microreactors have been used in many fields of chemistry such

• intensification and biocatalysis has been reviewed [24]. Asanomi et al. have also summarized the use of microfluidic devices in biocatalysis and compared them with conventional batch reactors [25]. The advantages of enzymatic microreactors have been demonstrated both in process development and for the production

• scale [26]. Similarly these reactors can provide high throughput opportunities, reduced reaction time with high conversion efficiency and high productivity per unit reaction volume for biocatalysis in fine chemistry [27]. These advantages have been demonstrated for reactions such as hydrolysis and

C–C Bond formation catalyzed by natural gelatin and collagen proteins

• Dennis Kühbeck,
• Basab Bijayi Dhar,
• Eva-Maria Schön,
• Carlos Cativiela,
• Vicente Gotor-Fernández and
• David Díaz Díaz

Beilstein J. Org. Chem. 2013, 9, 1111–1118, doi:10.3762/bjoc.9.123

• implications from a metabolic perspective. Keywords: biocatalysis; carbon–carbon bond formation; gelatin; Henry reaction; protein; Introduction Gelatin is a mixture of hot-water-soluble proteins of high average molecular weights (50–100 kDa) derived primarily from collagen, which is the main naturally

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

• Paweł Borowiecki,
• Małgorzata Milner-Krawczyk and
• Jan Plenkiewicz

Beilstein J. Org. Chem. 2013, 9, 516–525, doi:10.3762/bjoc.9.56

• biocatalysis [47][48], since solvents are able to change the activity [49][50][51] and enantioselectivity [52][53][54] of an enzyme. Conformational changes in the enzyme structure under the influence of solvent can even invert the substrate specificity and the enzyme–substrate affinity [55]. The ability to

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

• Zhi-Cong Geng,
• Jian Chen,
• Ning Li,
• Xiao-Fei Huang,
• Yong Zhang,
• Ya-Wen Zhang and
• Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

• synthesis of pyrazolidine derivatives by Wolfe et al. [33]. In the past decade, the research area of organocatalysis has grown rapidly and become a third brand of catalysis besides the well-established biocatalysis and metal catalysis [34][35][36][37][38][39][40][41][42][43][44]. Particularly

Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous

• Elaine O’Reilly,
• Suzanne J. Aitken,
• Gideon Grogan,
• Paul P. Kelly,
• Nicholas J. Turner and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2012, 8, 496–500, doi:10.3762/bjoc.8.56

• isomers in yields of up to 26%. Most interestingly, 2-(4-nitrobenzyloxy)tetrahydrofuran and 2-(4-nitrobenzyloxy)tetrahydropyran were transformed in high yields to the 4-hydroxylated and 5-hydroxylated products, respectively. Keywords: biocatalysis; cytochrome P450; hydroxylation; Rhodococcus rhodochrous

Chimeric self-sufficient P450cam-RhFRed biocatalysts with broad substrate scope

• Aélig Robin,
• Valentin Köhler,
• Alison Jones,
• Afruja Ali,
• Paul P. Kelly,
• Elaine O'Reilly,
• Nicholas J. Turner and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2011, 7, 1494–1498, doi:10.3762/bjoc.7.173

• high-throughput screening protocol for evaluating chimeric, self-sufficient P450 biocatalysts and their mutants against a panel of substrates was developed, leading to the identification of a number of novel biooxidation activities. Keywords: biocatalysis; C–H activation; high-throughput screening

• compounds, GC–MS traces of the biotransformation reactions and the MS traces of the corresponding starting materials. Supporting Information File 196: Experimental part and GC–MS traces. Acknowledgements We wish to thank the Centre of Excellence for Biocatalysis, Biotransformations and Biocatalytic

Coupled chemo(enzymatic) reactions in continuous flow

• Ruslan Yuryev,
• Simon Strompen and
• Andreas Liese

Beilstein J. Org. Chem. 2011, 7, 1449–1467, doi:10.3762/bjoc.7.169

• Ruslan Yuryev Simon Strompen Andreas Liese Institute of Technical Biocatalysis, Hamburg University of Technology, Denickestr. 15, 21073, Hamburg, Germany 10.3762/bjoc.7.169 Abstract This review highlights the state of the art in the field of coupled chemo(enzymatic) reactions in continuous flow

• . Three different approaches to such reaction systems are presented herein and discussed in view of their advantages and disadvantages as well as trends for their future development. Keywords: biocatalysis; chemo-enzymatic reaction sequences; continuous flow; coupled reactions; reaction cascades

• the field of applied biocatalysis, chemists are constantly trying to recognize the principles responsible for the efficiency of cell metabolism and to exploit them in organic synthesis [1][2][3]. There are three biological principles whose implementation may be regarded as important milestones in this

Efficient and selective chemical transformations under flow conditions: The combination of supported catalysts and supercritical fluids

• M. Isabel Burguete,
• Eduardo García-Verdugo and
• Santiago V. Luis

Beilstein J. Org. Chem. 2011, 7, 1347–1359, doi:10.3762/bjoc.7.159

• ] methodologies can improve significantly the energetic and synthetic efficiencies, as well as reaction selectivity, while reducing the production of concomitants. In this regard, biocatalysis-based transformations have an enormous potential, since they are able to increase stereo-, chemo- and regioselectivities

• ][84]. As a result, the chemical industry is currently exploring the great potential of biocatalysis to manufacture both bulk and fine chemicals [85][86]. Although many of the reported examples involve the use of batch conditions, different examples of continuous biocatalytic processes have been

Achiral bis-imine in combination with CoCl₂: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol

• K. Arunkumar,
• M. Appi Reddy,
• T. Sravan Kumar,
• B. Vijaya Kumar,
• K. B. Chandrasekhar,
• P. Rajender Kumar and
• Manojit Pal

Beilstein J. Org. Chem. 2010, 6, 1174–1179, doi:10.3762/bjoc.6.134

• the stereoselective synthesis of chiral molecules have increased enormously in recent years especially in the chemical and pharmaceutical industry [1]. Biocatalysis, being an environmentally friendly process, has attracted particular attention for this purpose [2][3][4][5][6]. For example, high

Hybrid biofunctional nanostructures as stimuli-responsive catalytic systems

• Gernot U. Marten,
• Thorsten Gelbrich and
• Annette M. Schmidt

Beilstein J. Org. Chem. 2010, 6, 922–931, doi:10.3762/bjoc.6.98

• , nanoparticulate biocatalysts that can easily be separated magnetically. The enzymatic activity of the obtained biocatalyst system can be influenced by outer stimuli, such as temperature and external magnetic fields, by utilizing the LCST of the copolymer shell. Keywords: biocatalysis; biolabelling; core–shell

Asymmetric reactions in continuous flow

• Xiao Yin Mak,
• Paola Laurino and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2009, 5, No. 19, doi:10.3762/bjoc.5.19

• this review. Applications of homogeneous and heterogeneous asymmetric catalysis as well as biocatalysis in flow are discussed. Keywords: asymmetric catalysis; biocatalysis; continuous flow; microreactors; solid phase synthesis; Introduction While many technological advancements have been made over

• case, a stainless steel ultrafiltration cell was fitted with a solvent-stable MPF-50 nanomembrane that was able to retain up to 98% of soluble catalyst 50. Under steady state conditions 70% conversion to the epoxide with up to 92% ee was achieved. Biocatalysis The usefulness of enzyme-driven catalysis

The first salen- type ligands derived from 3',5'-diamino- 3',5'-dideoxythymidine and -dideoxyxylothymidine and their corresponding copper(II) complexes

• Daniel Koth,
• Michael Gottschaldt,
• Helmar Görls and
• Karolin Pohle

Beilstein J. Org. Chem. 2006, 2, No. 17, doi:10.1186/1860-5397-2-17

• Daniel Koth Michael Gottschaldt Helmar Gorls Karolin Pohle Institute for Organic and Macromolecular Chemistry, FSU Jena, Humboldtstrasse 10, 07743 Jena, Germany Institute for Inorganic and Analytical Chemistry, FSU Jena, Lessingstrasse 8, 07743 Jena, Germany Biocatalysis and Organic Chemistry

Towards practical biocatalytic Baeyer- Villiger reactions: applying a thermostable enzyme in the gram- scale synthesis of optically- active lactones in a two-liquid- phase system

• Frank Schulz,
• François Leca,
• Frank Hollmann and
• Manfred T. Reetz

Beilstein J. Org. Chem. 2005, 1, No. 10, doi:10.1186/1860-5397-1-10

• well versed in the use of enzymes. Keywords: Baeyer-Villiger oxidation; monooxygenases; two-liquid-phase system; stereoselective catalysis; biocatalysis; Introduction First reported in 1899, the Baeyer-Villiger (BV) reaction of ketones with formation of esters or lactones has become a fundamental and

• active microbial cells.[27][28][29] Whole-cell biocatalysis, however, has some serious drawbacks such as the necessity to use specialized personnel and equipment which may not be a problem in industry, but certainly is for chemists in most academic laboratories. Moreover, yields are often low due to

• substrate- and product toxicity and undesired reactant metabolism.[30] Thus, organic chemists are often reluctant to use BVMOs as useful catalysts when planning synthetic routes. We therefore conclude that in the case of BVMOs, at least on mid-term basis, only in vitro biocatalysis has the potential of