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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
J Imperial et al.
Biochemistry, 28(19), 7796-7799 (1989-09-19)
(R)-2-Hydroxy-1,2,4-butanetricarboxylic acid [(R)-homocitrate] has been has been recently reported to be an integral constituent of the otherwise thought to be inorganic iron-molybdenum cofactor of dinitrogenase [Hoover, T.R., Imperial, J., Ludden, P.W., & Shah, V.K. (1989) Biochemistry 28,2768-2771]. Different organic acids
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