Synthese von S-Aspartyl-S-phenylalaninmethylester (aspartam) aus S-4-vinylazetidin-2-on

Pietsch, H.

doi:10.1016/s0040-4039(00)92573-5

Cited by 15 publications

(3 citation statements)

References 2 publications

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“…Aromatic metabolites such as tryptophan, phenylalanine, and tyrosine are essential amino acids for humans and animals. In addition, phenylalanine is used in aspartame production (15,19), and the tryptophan pathway can be modified to produce indigo (8). In E. coli, aromatic metabolites are generated from the condensation reaction between phosphoenolpyruvate (PEP) and erythrose 4-phosphate (E4P) to form 3-deoxy-D-arabinoheptulosonate 7-phosphate (DAHP).…”

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confidence: 99%

Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield

Patnaik

Liao

1994

Appl Environ Microbiol

189

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Escherichia coli and many other microorganisms synthesize aromatic amino acids through the condensation reaction between phosphoenolpyruvate (PEP) and erythrose 4-phosphate to form 3-deoxy-D-arabinoheptulosonate 7-phosphate (DAHP). It has been shown that overexpression of transketolase increases the production of DAHP in an aroB mutant strain (unable to further metabolize DAHP) with elevated DAHP synthase. However, the yield (percent conversion) of DAHP from glucose is still low. Stoichiometric analysis shows that many enzymes compete for intracellular PEP. In particular, the phosphotransferase system, responsible for glucose transport in E. coli, uses PEP as a phosphate donor and converts it to pyruvate, which is less likely to recycle back to PEP. This stoichiometric limitation greatly reduces the yield of aromatic metabolites. To relieve this limitation, we overexpressed PEP synthase in the presence of glucose and showed that it increased the final concentration and the yield of DAHP by almost twofold, to a near theoretical maximum. The PEP synthase effect is not observed without overproduced transketolase, suggesting that erythrose 4-phosphate is the first limiting metabolite. This result demonstrates the utility of pathway analysis and the limitation of central metabolites in the high-level overproduction of desired metabolites.

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confidence: 99%

Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield

Patnaik

Liao

1994

Appl Environ Microbiol

189

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“…The first problem to be overcome was the development of an efficient method for oxidation of the vinyl group. This oxidation has already been done (Pietsch, 1976); oxidation of vinylazetidin-one (15) with potassium permanganate in aqueous acetone provided 4-hydroxycarbonylazetidin-2-one (16) in 40 % yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Assigned Structure of Cairomycin A, 6-Isopropyl-2,5-Diketopiperazine-3-Acetic Acid and Its Β-Lactam Analogue N`- (3-Methyl-1-Hydroxybutyr-2-Yl) Azetidin-2-One-4-Carboximide

Hussain¹

2019

SJUOZ

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In the present investigation, the research carried out into the total synthesis of the assigned structure of cairomycin A, 6-isopropyl-2,5-diketopiperazine-3-acetic acid from its precursors L-valine and L-aspartic acid, and its analogue N`-(3-methyl-1-hydroxybutyr-2-yl)azetidin-2-one-4-carboximide from 4-vinylazetidi-2-one through two different sequence reactions. Structures of the synthesized products were identified by using chemical and physical methods such as elemental analysis, IR, 1H-NMR and MS. The obtained results were compared with those reported, it was found that neither of the synthesized compounds was Cairomycin A.

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“…(S)-4-(À)-Oxo-2-azetidinecarboxylic acid (I) and 3-azadinecarboxylic acid (II) are strained four-membered heterocycles, difficult to synthesize owing to unfavorable enthalpies of activation (Huszthy et al, 1993). Compound (I) is an optically active -lactam derivative of l-aspartic acid, which can be prepared by hydrogenation from (S)-4-(À)-benzyloxycarbonyl-2-azetidinone (Fritz et al, 1986), and by oxidation of 4-vinyl-2-azetidinone (Pietsch, 1976). Derivatives of (I) are of potential interest as precursors to -lactam antibiotics, since they can be converted into 4-acetoxy-2-azetidinones.…”

Section: Introductionmentioning

confidence: 99%

Structures of (S)-(−)-4-oxo-2-azetidinecarboxylic acid and 3-azetidinecarboxylic acid from powder synchrotron diffraction data

Mora

Brunelli

Fitch

et al. 2006

Acta Crystallogr Sect B

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Synthese von S-Aspartyl-S-phenylalaninmethylester (aspartam) aus S-4-vinylazetidin-2-on

Cited by 15 publications

References 2 publications

Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield

Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield

Synthesis of Assigned Structure of Cairomycin A, 6-Isopropyl-2,5-Diketopiperazine-3-Acetic Acid and Its Β-Lactam Analogue N`- (3-Methyl-1-Hydroxybutyr-2-Yl) Azetidin-2-One-4-Carboximide

Structures of (S)-(−)-4-oxo-2-azetidinecarboxylic acid and 3-azetidinecarboxylic acid from powder synchrotron diffraction data

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