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79156

Sigma-Aldrich

3-Deoxy-2-keto-6-phosphogluconic acid lithium salt

≥95% (TLC)

Synonyme(s) :

(4S,5R)-4,5-Dihydroxy-2-oxo-6-phosphonooxyhexanoic acid lithium salt, 2-Dehydro-3-deoxy-6-phospho-D-gluconate lithium salt, 2-Keto-3-deoxy-6-phosphogluconate lithium salt, 3-Deoxy-2-keto-D-gluconic acid 6-phosphate lithium salt, 3-Deoxy-D-erythro-hexulosonic acid 6-phosphate lithium salt, KDPG

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About This Item

Formule empirique (notation de Hill):
C6H11O9P · xLi+
Numéro CAS:
27244-54-8
Poids moléculaire :
258.12 (free acid basis)
Code UNSPSC :
12352201
Nomenclature NACRES :
NA.25

Niveau de qualité

100

Pureté

≥95% (TLC)

Forme

powder

Activité optique

[α]/D 9.0±1.0°, 3 hr, c = 0.1 in H2O

Couleur

white

Température de stockage

−20°C

InChI

1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1

Clé InChI

OVPRPPOVAXRCED-WVZVXSGGSA-N

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Actions biochimiques/physiologiques

2-dehydro-3-deoxy-phosphogluconate is a substrate for the enzyme 2-dehydro-3-deoxy-phosphogluconate aldolase which converts it into D-glyceraldehyde 3-phosphate plus pyruvate.
Metabolite in the pentose phosphate pathway, generating NADPH and pentoses; and in the in pentose and glucuronate interconversions; key intermediate in the Entner-Doudoroff pathway of some bacteria, substrate of 2-Keto-3-deoxy-6-phosphogluconate (KDPG) aldolase, catalyzing the reversible cleavage of KDPG to pyruvate and glyceraldehyde-3-phosphate. It was found to be the carbon catabolite repression signal of phenylacetic acid metabolism in P. putida KT2440. Expression from Pu was repressed mainly via PtsN in response to high levels of 2-dehydro-3-deoxygluconate-6-phosphate.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Juhyun Kim et al.
Microbiology (Reading, England), 155(Pt 7), 2420-2428 (2009-05-02)
The growth pattern of Pseudomonas putida KT2440 in the presence of glucose and phenylacetic acid (PAA), where the sugar is used in preference to the aromatic compound, suggests that there is carbon catabolite repression (CCR) of PAA metabolism by glucose
Stephen W B Fullerton et al.
Bioorganic & medicinal chemistry, 14(9), 3002-3010 (2006-01-13)
In vivo, 2-keto-3-deoxy-6-phosphogluconate (KDPG) aldolase catalyzes the reversible, stereospecific retro-aldol cleavage of KDPG to pyruvate and D-glyceraldehyde-3-phosphate. The enzyme is a lysine-dependent (Class I) aldolase that functions through the intermediacy of a Schiff base. Here, we propose a mechanism for
Teresa del Castillo et al.
Journal of bacteriology, 189(18), 6602-6610 (2007-07-10)
Pseudomonas putida KT2440(pWW0) can use toluene via the TOL plasmid-encoded catabolic pathways and can use glucose via a series of three peripheral chromosome-encoded routes that convert glucose into 6-phosphogluconate (6PG), namely, the glucokinase pathway, in which glucose is transformed to
Jonathan H Martin et al.
Journal of bacteriology, 200(17) (2018-06-20)
DeoR-type helix-turn-helix (HTH) domain proteins are transcriptional regulators of sugar and nucleoside metabolism in diverse bacteria and also occur in select archaea. In the model archaeon Haloferax volcanii, previous work implicated GlpR, a DeoR-type transcriptional regulator, in the transcriptional repression
Viatcheslav Zaitsev et al.
Biochemistry, 57(26), 3797-3806 (2018-05-31)
The thermoacidophilic archaea Picrophilus torridus and Sulfolobus solfataricus catabolize glucose via a nonphosphorylative Entner-Doudoroff pathway and a branched Entner-Doudoroff pathway, respectively. Key enzymes for these Entner-Doudoroff pathways are the aldolases, 2-keto-3-deoxygluconate aldolase (KDG-aldolase) and 2-keto-3-deoxy-6-phosphogluconate aldolase [KD(P)G-aldolase]. KDG-aldolase from P.
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