The Production of l-Erythrulose by the Action of Acetobacter suboxydans upon Erythritol

Whistler, Roy L.; Underkofler, L. A.

doi:10.1021/ja01277a065

Cited by 35 publications

(10 citation statements)

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“…The optical rotation data for 3 was very similar to that reported by Bolte et [12] ). HPLC analysis of 5, and comparison to triacetylated l-erythrulose (l-erythrulose available commercially) indicated that 3 had been formed in 95% ee (S major isomer).…”

Section: Stereoselectivities Of Wt Ecoli Tksupporting

confidence: 87%

“…[5] With glycolaldehyde and non-a-hydroxylated substrates, although optical rotations have generally been reported, enantiomeric purities are not. [6] For example, when glycolaldehyde was reacted with 1 and spinach TK to give 3, the authors stated that the stereospecificity seems very high (optical rotation data [ [12] ), although the enantiomeric purity of the products was not fully assessed.…”

Section: Introductionmentioning

confidence: 99%

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Enhancing and Reversing the Stereoselectivity of Escherichia coli Transketolase via Single‐Point Mutations

et al. 2008

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Chiral auxiliary methodology and chiral assays have been developed to establish the enantiomeric purities of erythrulose and 1,3-dihydroxypentan-2-one generated using wild-type (WT) Escherichia coli transketolase (TK). l-Erythrulose was formed in 95% ee and (3S)-1,3-dihydroxypentan-2-one in 58% ee. Since the latter compound was formed in moderate ee, TK libraries were screened to identify higher performing mutants. A colorimetric screen and chiral assay were successfully applied to a 96-well format, and new active TK mutants were identified, which gave 1,3-dihydroxypentan-2-one in high stereoselectivities. Remarkably, activesite single-point mutants were identified that were able to both enhance and reverse the stereoselectivity of TK.

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Section: Stereoselectivities Of Wt Ecoli Tksupporting

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Enhancing and Reversing the Stereoselectivity of Escherichia coli Transketolase via Single‐Point Mutations

et al. 2008

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“…Material in the medium containing radiotracer has not been identified but paper chromatography has excluded the presence of significant amounts of erythrose or erythrulose which might have been formed by the partial oxidation of erythritol as occurs with Acetobacter suboxydans (Whistler & Underkofler, 1938). Only small amounts of radiotracer were present in glucose and glycerol regions of autoradiograms, although large amounts of glycerol were excreted into the medium.…”

Section: Resultsmentioning

confidence: 99%

The Metabolism of Erythritol by Brucella abortus

Anderson

Smith

1965

Journal of General Microbiology

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SUMMARYThe growth of a virulent strain of Brucella abortus was stimulated by low concentrations of erythritol in a medium containing high concentrations of glucose and a wide range of amino acids. During growth in this medium the organisms used about 14 times their weight of erythritol as a carbon and energy source. The effect of erythritol was specific, since several C, to C, homologues had no growth-stimulating activity. Radiotracer studies showed that a large proportion of the carbon of the erythritol was excreted as carbon dioxide; that remaining in the organisms was fairly uniformly distributed over all components. Erythritol and 2-deoxy-2-fluoro-DL-erythritol inhibited incorporation of glucose by the organism.

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“…Thus a polyol with the D-erythro configuration (I) is oxidized mainly a t the secondary alcohol group adjacent to the terminal primary alcohol to give a ketose (11). Many examples of this reaction have been reported (3,4,5,6,7,8). More recently, cell-free extracts have been used for the oxidation of some polyols in an alkaline e~lvironment (optimum pH 7.8), although the reaction is less specific since polyols possessirlg either the L-threo-(111) or D-erythro-(I) configurations \vere utilized (9).…”

Section: Introductionmentioning

confidence: 99%

The Oxidation of Some Terminal-Substituted Polyhydric Alcohols by Acetobacter Suboxydans

Hough¹,

Jones²,

Mitchell³

1959

Can. J. Chem.

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Various terminal-substituted pentitols and hexitols, which possessed either the L-lyxo-or the D-ribo-configuration a t the three contiguous carbon atoms adjacent t o the terminal carbon atom, were oxidized to lcetoses by Acetobacter suboxydans. The terminal hydrosyl group of the polyol was replaced by -H, -ObIe, -SEt, and -0Ac groups; several 1,l-dithioacetal derivatives of aldoses were also tested. The preparation of 1-0-acetyl-DL-galactitol, l-deoxy-1-S-ethyl-D-arabitol, and 6-deoxy-6-S-ethyl-L-sorbose are described. 6-Deoxy-6-S-ethyl-Lsorbose was prepared by the microbiological oxidation of 1-deoxy-1-S-ethyl-D-glucitol. INTRODUCTIONThe oxidation of unsubstituted sugar alcohols by proliferating cells of Acetobacter suboxydans has resulted in the formulation of the Bertrand-Hudson rule for oxidations occurring within the pH range of 5-6.5 (1, 2). Thus a polyol with the D-erythro configuration (I) is oxidized mainly a t the secondary alcohol group adjacent to the terminal primary alcohol to give a ketose (11). Many examples of this reaction have been reported (3,4,5,6,7,8). More recently, cell-free extracts have been used for the oxidation of some polyols in an alkaline e~lvironment (optimum pH 7.8), although the reaction is less specific since polyols possessirlg either the L-threo-(111) or D-erythro-(I) configurations \vere utilized (9).Investigation of the microbiological oxidation of various w-deoxy-sugar alcohols a t pH 5-6.5 has shown that w(n)-deoxy-polyols with the D-erytkro configuration a t the carbon atonls (72-2) and (72-3) (where n equals the number of carbons in the chain) (e.g. VI and VII) gave copper reducing products even when the favorable D-erythro configuration was absent a t the other end of the chain (10, 11). This configuration is present ill I>-fucitol (6-deoxy-L-galactitol) (IV), which has been shown to be oxidized a t carbon 4 to give 1-deoxy-D-xylo-3-hexulose (1~-fuc0-4-ketose) (V). I-Iudson, Stewart, and Richtmyer reconciled this evidence with the k11ow11 specificity of the organism by suggesting that the secondary alcohol a t carbon 5 of 6-deoxy-L-galactitol (IV), which can be considered as a C-methyl derivative of a pentitol, serves a t the enzyme surface in a capacity similar to the primary alcohol of an u~~substituted acyclic polyol. We have investigated the specificity of this microbiological oxidation with a view to the preparation of 3-hexuloses and 3-pentuloses.A limited number of polyols which possess the favorable D-ribo-(VI) or L-lyxo-(VII) configuration adjacent to a substituent other than hydroxyl a t the terminal carbon atom have been tested as substrates for A. suboxydans and some gave reducing products. The substituents included a hydrogen atom (w-deoxy), w-0-methyl, w-deoxy-w-Sethyl, and an w-0-acetyl group. All of the unbranched polyols except 1-deoxy-1-S-ethyl-Larabitol were oxidized to reducing products, which unlike the polyols gave bright yellow or orange spots with p-anisidine hydrochloride on paper chromatograms. Similar color reactions were reported for 2-0-me...

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The Production of l-Erythrulose by the Action of Acetobacter suboxydans upon Erythritol

Cited by 35 publications

References 0 publications

Enhancing and Reversing the Stereoselectivity of Escherichia coli Transketolase via Single‐Point Mutations

Enhancing and Reversing the Stereoselectivity of Escherichia coli Transketolase via Single‐Point Mutations

The Metabolism of Erythritol by Brucella abortus

The Oxidation of Some Terminal-Substituted Polyhydric Alcohols by Acetobacter Suboxydans

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