Pyrazine Biosynthesis in <i>Corynebacterium glutamicum</i>

Dickschat, Jeroen S.; Wickel, Susanne M.; Bolten, Christoph J.; Nawrath, Thorben; Schulz, Stefan; Wittmann, Christoph

doi:10.1002/ejoc.201000155

Cited by 125 publications

(129 citation statements)

References 28 publications

(56 reference statements)

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“…The first of these, the enzymatic condensation biogenic pathway, has been supported by several authors [19]. However, the enzymes or genes responsible for the condensation reaction have never been reported.…”

Section: The Second Step: Accelerated Spontaneous Formation Of Tmpmentioning

confidence: 93%

Accelerated green process of tetramethylpyrazine production from glucose and diammonium phosphate

Xiao

Hou

Lyu

et al. 2014

Biotechnol Biofuels

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Section: The Second Step: Accelerated Spontaneous Formation Of Tmpmentioning

confidence: 93%

Accelerated green process of tetramethylpyrazine production from glucose and diammonium phosphate

Xiao

Hou

Lyu

et al. 2014

Biotechnol Biofuels

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“…The unique nutty and roasted odor characteristics of pyrazines resulted in a significantly different odor compared to traditional fermented soybean products, i.e., fermented stinky tofu, which contained sulfide compounds for more than 15 % of its contents but does not have any pyrazine compounds at all [11]. The biosynthetic formation of pyrazines may be attributed to the addition of acetoin, where this addition in fermenting medium resulted in the incorporation of the acetoin substance into 2,3,5-trimethylpyrazine [12]. Furthermore, the biosynthesis of acetoin might be formed from pyruvate via α-acetolactate [13].…”

Section: Resultsmentioning

confidence: 99%

Teratogenicity and volatile composition evaluation of soymilk fermented with a Deinococcus member

Li¹,

Chen²,

Lin³

et al. 2017

J Toxicol Health

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The possibility of producing functional ingredients based on soymilk, fermented with a new identified strain Deinococcus sp. GKB-Aid 1995, was examined. Firstly, a prenatal developmental toxicity test in Sprague-Dawley rats was conducted to assess any potential human health risk. Next, owing to the unique odor that is significantly different from traditional fermented soymilk products, investigations on specific volatile compositions of GKB-Aid 1995 fermented soymilk are pivotal to the study. The results showed that there was no any detrimental effect on fetal and skeletal development under the highest dose of GKB-Aid 1995 fermented soymilk (3 g/kg body weight/day) during 20 days of the study. HS-SPME-GC-MS analysis indicated that a total of 35 identified volatile compounds were found in this new functional ingredient. In conclusion, smell of the GKB-Aid 1995 fermented soymilk, varied from the unpleasant odor of general soymilk products, has shown its possibility as a new source of functional ingredient.

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“…These results rule out a piperazinedione intermediate in the biosynthesis of dialkylated pyrazines of the second class as proposed in Scheme 2. Instead, a pathway via an unstable a-amino aldehyde intermediate seems more likely (Scheme 6), similar to the biosynthesis of alkylated pyrazines from acetoin and related a-hydroxycarbonyl compounds [7]. Valine (10) is reduced to the highly reactive a-amino-aldehyde intermediate 35 that can dimerize by two condensation reactions to form the dihydropyrazine 36.…”

mentioning

confidence: 98%

“…Recently, we have shown by a combination of gene knockout and feeding experiments that the biosynthetic pathway to the first class of pyrazines in C. glutamicum includes a sequence of transamination and oxidation of acetoin ( ¼ 3-hydroxybutan-2-one; 6) and its higher homologues to a-amino ketones, followed by condensation and oxidation [7] (Scheme 1).…”

mentioning

confidence: 99%

The Biosynthesis of Branched Dialkylpyrazines in Myxobacteria

Nawrath

Dickschat

Kunze

et al. 2010

Chemistry & Biodiversity

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The biosynthesis of the volatiles 2,5- and 2,6-diisopropylpyrazine (2 and 3, resp.) released by the myxobacteria Nannocystis exedens subsp. cinnabarina (Na c29) and Chondromyces crocatus (strains Cm c2 and Cm c5) was studied. Isotopically labeled precursors and proposed pathway intermediates were fed to agar plate cultures of the myxobacteria. Subsequently, the volatiles were collected by use of a closed loop stripping apparatus (CLSA), and incorporation into the pyrazines was followed by GC/MS analysis. [(2)H(8)]Valine was smoothly incorporated into both pyrazines clearly establishing their origin from the amino acid pool. The cyclic dipeptide valine anhydride (16)--a potential intermediate on the biosynthetic pathway to branched dialkylpyrazines--was synthesized containing (2)H(1) labels in specific positions. Feeding of [(2)H(16)]-16 and [(2)H(12)]-16 in both valine subunits mainly resulted in the formation of pyrazines derived from only one labeled amino acid, whereas only traces of the expected pyrazines with two labeled subunits were found. To investigate the origin of nitrogen in the pyrazines, a feeding experiment with [(15)N]valine was performed, resulting in the incorporation of the (15)N label. The results contradict a biosynthetic pathway via cyclic dipeptides, but rather point to a pathway on which valine is reduced to valine aldehyde. Its dimerization to 2,5-diisopropyldihydropyrazine 36 and subsequent oxidation results in 2. The proposed biosynthetic pathway neatly fits the results of earlier labeling studies and also explains the formation of the regioisomer 2,6-diisopropylpyrazine 3 by isomerization during the first condensation step of two molecules valine aldehyde. A general biosynthetic pathway to different classes of pyrazines is presented.

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Pyrazine Biosynthesis in Corynebacterium glutamicum

Cited by 125 publications

References 28 publications

Accelerated green process of tetramethylpyrazine production from glucose and diammonium phosphate

Accelerated green process of tetramethylpyrazine production from glucose and diammonium phosphate

Teratogenicity and volatile composition evaluation of soymilk fermented with a Deinococcus member

The Biosynthesis of Branched Dialkylpyrazines in Myxobacteria

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