Enantiocomplementary inverting sec-alkylsulfatase activity in cyano- and thio-bacteria Synechococcus and Paracoccus spp.: selectivity enhancement by medium engineering

Gadler, Petra; Reiter, Tamara; Hoelsch, Kathrin; Weuster‐Botz, Dirk; Faber, Kurt

doi:10.1016/j.tetasy.2009.01.007

Cited by 8 publications

(12 citation statements)

References 51 publications

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“…Through follow-up of an observation that cyano-and thiobacteria from Synechococcus and Paracoccus species, respectively, furnished either (R)-or (S)-secondary alcohols from the corresponding racemic sulfate esters in an enantiocomplementary fashion, Kurt Faber's group at the University of Graz (Austria) found broad-spectrum inverting alkylsulfatases, for which no complement in chemistry exists (64). Medium engineering dramatically improved enantioselectivity: addition of lower alcohols or use of methyl tert-butyl ether in a biphasic system improved the E value from approximately 4 to >200.…”

Section: Novel Biocatalysts Through Finding New Reactionsmentioning

confidence: 99%

Biocatalysis: A Status Report

Bommarius

2015

Annu. Rev. Chem. Biomol. Eng.

136

101

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This review describes the status of the fields of biocatalysts and enzymes, as well as existing drawbacks, and recent advances in the areas deemed to represent drawbacks. Although biocatalysts are often highly active and extremely selective, there are still drawbacks associated with biocatalysis as a generally applicable technique: the lack of designability of biocatalysts; their limits of stability; and the insufficient number of well-characterized, ready-to-use biocatalysts. There has been significant progress on the following fronts: (a) novel protein engineering tools, both experimental and computational, have significantly enhanced the toolbox for biocatalyst development. (b) The deactivation of biocatalysts under various stresses can be described quantitatively via rational models. There are several cases of spectacular leaps of stabilization after accumulating all stabilizing mutations found in earlier rounds. The concept that stabilization against one type of stress commonly also stabilizes against other types of stress is now experimentally considerably better founded than a few years ago.

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Section: Novel Biocatalysts Through Finding New Reactionsmentioning

confidence: 99%

Biocatalysis: A Status Report

Bommarius

2015

Annu. Rev. Chem. Biomol. Eng.

136

101

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“…FCC 175B 4<52(Gadler and Faber 2007b) Actinobacteria Rhodococcus ruber DSM 44541 e A 5,8<5n.a.(Gadler and Faber 2007a)B 3,4,5,6,7,12,14,15,19 C 24–681–21(Pogorevc and Faber 2002) Gulosibacter molinativorax DSM 13485B 4>105(Gadler and Faber 2007b) Nocardia nova DSM 43843B 4>10(Gadler and Faber 2007b) Planctomycetes Rhodopirellula baltica DSM 10527A 526n.a.(Wallner et al 2005a)B 3,4,5,12,14 C 2,5<5–182– > 200 Cyanobacteria Synechococcus sp. PCC 7942B 3,4,5,12,14<5–241–3(Gadler et al 2009)C 55–104– > 200 d Synechococcus sp. RCC 556B 3,4,5,12,14<5–10n.d./1(Gadler et al 2009) Firmicutes Bacillus cereus A 9n.d.n.a.(Singh et al 1998) Bacillus sphaericus FCC 098B 4<51(Gadler and Faber 2007b) Strain combination Acinetobacter calcoaceticus + Pantoea agglomerans A 9n.d.n.a.(Abboud et al 2007)Archaea Crenarchaeota Sulfolobus acidocaldarius DSM 639B 3,4,5,12,14,1910–435– > 200(Gadler and Faber 2007a; Wallner et al 2004)C 55–10n.d.E 2,35–102 Sulfolobus solfataricus DSM 1617B 4,1920–562–35(Wallner et al 2005b) Sulfolobus shibatae DSM 5389B 4,1920–432–48…”

Section: Search For Sulfatase Activitymentioning

confidence: 99%

“…PCC 7942B 3,4,5,12,14<5–241–3(Gadler et al 2009)C 55–104– > 200 d Synechococcus sp. RCC 556B 3,4,5,12,14<5–10n.d./1(Gadler et al 2009) Firmicutes Bacillus cereus A 9n.d.n.a.(Singh et al 1998) Bacillus sphaericus FCC 098B 4<51(Gadler and Faber 2007b) Strain combination Acinetobacter calcoaceticus + Pantoea agglomerans A 9n.d.n.a.(Abboud et al 2007)Archaea Crenarchaeota Sulfolobus acidocaldarius DSM 639B 3,4,5,12,14,1910–435– > 200(Gadler and Faber 2007a; Wallner et al 2004)C 55–10n.d.E 2,35–102 Sulfolobus solfataricus DSM 1617B 4,1920–562–35(Wallner et al 2005b) Sulfolobus shibatae DSM 5389B 4,1920–432–48(Wallner et al 2005b) Sulfolobus metallicus DSM 6482B 45–101(Wallner et al 2005b) Sulfolobus hakoniensis DSM 7519B 45–101(Wallner et al 2005b) Acidianus brierley DSM 1651B 45–101(Wallner et al 2005b) Acidianus infernus DSM 3191B 4251(Wallner et al 2005b) Acidianus ambivalens DSM 3772B 4131(Wallner et al 2005b) Metallosphaera sedula DSM 5348B 45–101(Wallner et al 2005b) Sulfurisphaera ohwakuensis DSM 12421B 4111(Wallner et al 2005b) n.a. not applicable, n.d. not determine...…”

Section: Search For Sulfatase Activitymentioning

confidence: 99%

Microbial alkyl- and aryl-sulfatases: mechanism, occurrence, screening and stereoselectivities

Toesch

Schöber

Faber

2013

Appl Microbiol Biotechnol

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This review gives an overview on the occurrence of sulfatases in Prokaryota, Eukaryota and Archaea. The mechanism of enzymes acting with retention or inversion of configuration during sulfate ester hydrolysis is discussed taking two complementary examples. Methods for the discovery of novel alkyl sulfatases are described by way of sequence-based search and enzyme induction. A comprehensive list of organisms with their respective substrate scope regarding prim- and sec-alkyl sulfate esters allows to assess the capabilities and limitations of various biocatalysts employed as whole cell systems or as purified enzymes with respect to their activities and enantioselectivities. Methods for immobilization and selectivity enhancement by addition of metal ions or organic (co)solvents are summarised.

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“…In a subsequent set of reactions, enantioenriched compounds ent-A and B are transformed into a single product C; one of these transformations proceeds with retention and the other with inversion of configuration. [22][23][24] The follow-up chemical hydrolysis of the enantioenriched sulfate ester proceeds with retention of configuration and gives the same enantiomer of the alcohol as the one produced in the enzymatic inverting step. [21] The third approach (Figure 1 c) relies on the use of a single enantioinverting enzyme for the conversion of one of the enantiomers of substrate A into product B.…”

mentioning

confidence: 99%

“…Most recent examples of such syntheses include the use of inverting alkyl sulfatases for enantioselective sulfate ester hydrolysis, which produces an alcohol and an unreacted enantiomer of the sulfate ester, both with the same absolute configuration. [22][23][24] The follow-up chemical hydrolysis of the enantioenriched sulfate ester proceeds with retention of configuration and gives the same enantiomer of the alcohol as the one produced in the enzymatic inverting step.…”

mentioning

confidence: 99%

A Simple Enantioconvergent and Chemoenzymatic Synthesis of Optically Active α‐Substituted Amides

et al. 2011

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Enantiopure amides 1, substituted in the a position with an azide or a simple N, O, or S substituent (Scheme 1), form an important class of compounds and are key intermediates in medicinal chemistry. The a-azidoamide motif (1, Nu = N 3 ) is found in bioactive molecules, such as the antibiotic azidocillin (Scheme 1). The azide group is considered to be an isostere of the amino group, however, it has increased bulkiness and is not positively charged at physiological pH values. [1] The introduction of an azide function into the a position of peptides is also aimed at the synthesis of enzyme inhibitors that, after binding to their targets and subsequent Staudingertype ligation with biotin-phosphine, are subjected to streptavidin pull-down. [2] Furthermore, enantiopure a-azidoamides are important reagents for "click" chemistry [3] and valuable precursors in the synthesis of amino acids [4] and peptides. [5,6] The chiral scaffold of an amide with a simple O substituent (1, Nu = OR) in the a position can be found in numerous bioactive compounds, such as solimastat (Scheme 1), which is an inhibitor of matrix metalloproteinase, [7] and other anticancer [8] and anticonvulsant [9] agents. Bioactive molecules that bear a chiral amide motif with an S substituent (1, Nu =[*] Dr.

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Enantiocomplementary inverting sec-alkylsulfatase activity in cyano- and thio-bacteria Synechococcus and Paracoccus spp.: selectivity enhancement by medium engineering

Cited by 8 publications

References 51 publications

Biocatalysis: A Status Report

Biocatalysis: A Status Report

Microbial alkyl- and aryl-sulfatases: mechanism, occurrence, screening and stereoselectivities

A Simple Enantioconvergent and Chemoenzymatic Synthesis of Optically Active α‐Substituted Amides

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