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06711

Sigma-Aldrich

D-(−)-Citramalic acid lithium salt

≥95.0% (GC)

Synonym(s):

(R)-2-Hydroxy-2-methylsuccinic acid lithium salt, D-(−)-2-Methylmalic acid lithium salt

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About This Item

Empirical Formula (Hill Notation):
C5H8O5 · xLi+
CAS Number:
6236-10-8
Molecular Weight:
148.11 (free acid basis)
Beilstein:
1723818
UNSPSC Code:
12352204
NACRES:
NA.32

Assay

≥95.0% (GC)
4-9% (Lithium, ICP)

form

powder or crystals

optical activity

[α]/D -19.0±2.0°, c = 0.5 in 1 M HCl

storage temp.

2-8°C

SMILES string

C[C@@](O)(CC(O)=O)C(O)=O

InChI

1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)/t5-/m1/s1

InChI key

XFTRTWQBIOMVPK-RXMQYKEDSA-N

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Biochem/physiol Actions

Citramalate is a biochemical intermediate known to be involved in several aspects of bacterial metabolism, including, among others, the anaerobic metabolism of glutamate via the methylaspartate pathway of Clostridium tetanomorphum.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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W Buckel et al.
Journal of bacteriology, 117(3), 1248-1260 (1974-03-01)
Two pathways are involved in the fermentation of glutamate to acetate, butyrate, carbon dioxide, and ammonia-the methylaspartate and the hydroxyglutarate pathways which are used by Clostridium tetanomorphum and Peptococcus aerogenes, respectively. Although these pathways give rise to the same products
I du Preez et al.
Tuberculosis (Edinburgh, Scotland), 93(3), 330-337 (2013-03-13)
In this study, a metabolomics research approach was used to identify new tuberculosis (TB) markers from sputum, in an attempt to better characterise the disease as well as the metabolic response of the host to Mycobacterium tuberculosis infection. After GCxGC-TOFMS
Ilana Chefetz et al.
Cell reports, 26(11), 3061-3075 (2019-03-14)
Ovarian cancer is typified by the development of chemotherapy resistance. Chemotherapy resistance is associated with high aldehyde dehydrogenase (ALDH) enzymatic activity, increased cancer "stemness," and expression of the stem cell marker CD133. As such, ALDH activity has been proposed as a
Hai Xu et al.
Journal of bacteriology, 186(16), 5400-5409 (2004-08-05)
Three leuA-like protein-coding sequences were identified in Leptospira interrogans. One of these, the cimA gene, was shown to encode citramalate synthase (EC 4.1.3.-). The other two encoded alpha-isopropylmalate synthase (EC 4.1.3.12). Expressed in Escherichia coli, the citramalate synthase was purified
D M Howell et al.
Journal of bacteriology, 181(1), 331-333 (1998-12-29)
The Methanococcus jannaschii gene MJ1392 was cloned, and its protein product was hyperexpressed in Escherichia coli. The resulting protein was purified and shown to catalyze the condensation of pyruvate and acetyl coenzyme A, with the formation of (R)-citramalate. Thus, this
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