Supercritical Biocatalysis

Mesiano, Anita J.; Beckman, Eric J.; Russell, Alan J.

doi:10.1021/cr970040u

Cited by 259 publications

(134 citation statements)

References 61 publications

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“…[1][2][3][4] In particular, efforts to develop molecules and materials that can be easily solvated in scCO 2 have led to the discovery of weak electron donor-acceptor (EDA) interactions between CO 2 (Lewis acid, LA) and compounds containing fluorine atoms (Lewis base, LB), such as fluorinated polymers. [5] The next milestone for advances in the development of CO 2 -philic molecules was represented by the characterization of EDA interactions between CO 2 and carbonyl groups.…”

Section: Introductionmentioning

confidence: 99%

Theoretical insights on electron donor–acceptor interactions involving carbon dioxide

San‐Fabián

Ingrosso

Lambert

et al. 2014

Chemical Physics Letters

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Section: Introductionmentioning

confidence: 99%

Theoretical insights on electron donor–acceptor interactions involving carbon dioxide

San‐Fabián

Ingrosso

Lambert

et al. 2014

Chemical Physics Letters

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“…72,78,[81][82][83][84] The chief advantage of SCFs is the tunability of the properties of the solvent, through slight changes of the pressure and/or temperature. It is well established that success of biocatalysis (i.e.…”

Section: Methodsmentioning

confidence: 99%

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

Milner¹,

Maguire²

2012

Arkivoc

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Modern synthetic organic chemistry has experienced an enormous growth in biocatalytic methodologies; enzymatic transformations and whole cell bioconversions have become generally accepted synthetic tools for asymmetric synthesis. This review details an overview of the latest achievements in biocatalytic methodologies for the synthesis of enantiopure compounds with a particular focus on chemoenzymatic synthesis in non-aqueous media, immobilisation technology and dynamic kinetic resolution. Furthermore, recent advances in ketoreductase technology and their applications are also presented.Keywords: Biocatalysis, kinetic and dynamic kinetic resolution, Baker's yeast, ketoreductases General IntroductionAsymmetric synthesis is the preferential formation of one stereoisomer of a chiral target compound to another; when scientists at GlaxoSmithKline, AstraZeneca and Pfizer 1 examined 128 syntheses from their companies, they found as many as half of the drug compounds made by their process research and development groups are not only chiral but also contain an average of two chiral centres each. 2In 2006 just 25 % were derived from the chiral pool and over 50 % employed chiral technologies. 1In order to meet regulatory requirements enantiomeric purities of 99.5 % were deemed necessary by the FDA. 3 This is one of the biggest challenges which face chemists today, primarily due to the recognition of the fact that different enantiomers of the same compound can interact differently in biological systems. As a consequence, the production of single enantiomers instead of racemic mixtures has become an important process in the pharmaceutical and agrochemical industry. Several routes can lead to the desired enantiomer including transition metal-, [4][5][6] organo-5,7-10 and bio-catalysis [11][12][13][14][15] and these have been thoroughly reviewed in the literature. 16,17 2. Biocatalysis IntroductionBiocatalysis involves the use of enzymes or whole cells (containing the desired enzyme or enzyme system) as catalysts for chemical reactions. A timeline of historic events in biocatalysis and biotechnology is outlined in Table 1. [18][19][20] Reviews and Accounts Novel methodologies for discovering industrial enzymes based on genomic sequencing and phage display (discussed further in Section 1.3), 21,22 as well as highly effective optimisation tools based on chemical, physical and molecular biology approaches, 23 have improved the access to biocatalysts, increased their stability, and radically broadened their specificity. 24This greater availability of catalysts with superior qualities including the use of new bioengineering tools contributed significantly to the development of new industrial processes. Biocatalytic methodologies for organic synthesis were outlined by Woodley et al. in three categories: established, emerging and expanding chemistries as depicted in Figure 1. 25 Enzyme classesBy the late 1950s it had become evident that the nomenclature of enzymes without any guiding authority, in a period when the...

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“…2000a). These reaction media, that include organic solvents (Clark, 2004;Gupta and Roy, 2004), supercritical fluids (Kamat et al 1992;Mesiano et al 1999), eutectic mixtures (Gill and Vulfson, 1994), solid-state (Halling et al 1995;Erbeldinger et al 1998) and, more recently, ionic liquids (Park and Kazlauskas, 2003;van Rantwijk et al 2003;Lou et al 2004;Machado and Saraiva, 2005) offer other potential advantages as well: the possibility of using poorly water soluble substrates; the modification of the equilibrium of reaction as a consequence of the alteration of the partition coefficients of substrates and products in the case of biphasic systems; the reduction of inhibitory effects by substrates and products; the easiness of biocatalyst and product recovery; the increase in the thermostability of the biocatalyst and, in some cases, the variation in substrate specificity and the increase in the stereo and enantiospecificity in the resolution of racemic mixtures (Kawashiro et al 1997;Klibanov 2001). As compared to chemical synthesis, a most important advantage of biocatalysis is the specificity of the reaction, which reduces the requirement of side-chain protection.…”

Section: Proteases In Peptide Synthesismentioning

confidence: 99%

Peptide synthesis: chemical or enzymatic

Guzmán

Barberis

Illanes

2007

Electron. J. Biotechnol.

178

139

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Abbreviations:CD 280synthesis is probably the way to go, since the good properties of each technology can be synergistically used in the context of one process objective.Peptides are heteropolymers composed by amino acid residues linked by peptidic bonds between the carboxyl group of one amino acid residue and the α-amino group of the next one. The definition is rather vague in terms of chain length, peptides ranging from two to a few dozens residues. Its lower limit of molecular mass has been set rather arbitrarily in 6000 Da; molecules larger than that are considered proteins. Peptides are molecules of paramount importance in several fields, especially in health care and nutrition. The case of the hormone insulin (51 residues, 5773 Da) and the non-caloric sweetener aspartame (a dipeptide of aspartic acid and esterified phenylalanine) are relevant examples of those fields of application and the range of molecular size. Medium to small size peptides are, however, the most relevant for such applications.

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Supercritical Biocatalysis

Cited by 259 publications

References 61 publications

Theoretical insights on electron donor–acceptor interactions involving carbon dioxide

Theoretical insights on electron donor–acceptor interactions involving carbon dioxide

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

Peptide synthesis: chemical or enzymatic

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