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D4288

Sigma-Aldrich

Digalacturonic acid

≥85% (HPLC)

Synonym(s):
α-D-GalA-(1→4)-D-GalA
Empirical Formula (Hill Notation):
C12H18O13
CAS Number:
Molecular Weight:
370.26
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

biological source

synthetic (organic)

assay

≥85% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

OC(C=O)C(O)C(OC1OC(C(O)C(O)C1O)C(O)=O)C(O)C(O)=O

InChI

1S/C12H18O13/c13-1-2(14)3(15)8(7(19)10(20)21)24-12-6(18)4(16)5(17)9(25-12)11(22)23/h1-9,12,14-19H,(H,20,21)(H,22,23)

InChI key

SYBQLSSECRIKMJ-UHFFFAOYSA-N

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Application

Digalacturonic acid (DGA), derived in vivo from pectin catabolism, is used for the co-crystallization of enzymes such as proteinase K. It is used in galacturonic acid metabolism research as a substrate to identify, differentiate and characterized endo- and exopolygalacturonase(s) and gluconase(s). DGA is used to study the transport of oligogalacturonides by systems such as the TogMNAB ABC transporter.

Packaging

10, 25, 100 mg in poly bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D4288.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Lisha Zhang et al.
Fungal genetics and biology : FG & B, 48(10), 990-997 (2011-06-21)
D-galacturonic acid is the most abundant component of pectin, one of the major polysaccharide constituents of plant cell walls. Galacturonic acid potentially is an important carbon source for microorganisms living on (decaying) plant material. A catabolic pathway was proposed in
V E Miamin et al.
Genetika, 40(9), 1187-1193 (2004-11-24)
A mutant that cannot utilize pectin substances of plant cell walls was obtained via insertion of mini-mini-Tn5xylE transposon into the chromosome of phytopathogenic bacteria Erwinia carotovora subsp. atroseptica. The inability of mutant cells to utilize these substrates was caused by
V Valmeekam et al.
Molecular plant-microbe interactions : MPMI, 14(6), 816-820 (2001-06-02)
The negative regulatory protein ExuR in Erwinia chrysanthemi regulates expression of the galacturonate uptake (exuT) and utilization (uxaA, uxaB, uxaC) genes. We cloned and determined the nucleotide sequence of the exuR gene from E. chrysanthemi EC16. Analysis of the deduced
N Hugouvieux-Cotte-Pattat et al.
Molecular microbiology, 41(5), 1113-1123 (2001-09-14)
The bacterium Erwinia chrysanthemi, which causes soft rot disease on various plants, is able to use pectin as a carbon source for growth. Knowledge of the critical step in pectin catabolism which allows the entry of pectic oligomers into the
S Gognies et al.
Journal of industrial microbiology & biotechnology, 39(7), 1023-1029 (2012-03-01)
In Saccharomyces cerevisiae, an endopolygalacturonase encoded by the PGL1 gene catalyzes the random hydrolysis of the α-1,4 glycosidic linkages in polygalacturonic acid. To study the regulation of the PGL1 gene, we constructed a reporter vector containing the lacZ gene under

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