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333115

Sigma-Aldrich

2-Isopropylmalic acid

98%

Synonym(s):

2-Hydroxy-2-isopropylsuccinic acid

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About This Item

Linear Formula:
HO2CCH2C[CH(CH3)2](OH)CO2H
CAS Number:
3237-44-3
Molecular Weight:
176.17
MDL number:
MFCD00075003
UNSPSC Code:
12352100
PubChem Substance ID:
24860103
NACRES:
NA.22

assay

98%

mp

144-146 °C (lit.)

SMILES string

CC(C)C(O)(CC(O)=O)C(O)=O

InChI

1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)

InChI key

BITYXLXUCSKTJS-UHFFFAOYSA-N

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General description

2-Isopropylmalic acid is an intermediate formed during leucine biosynthesis. Budding yeast Saccharomyces cerevisiae secrets 2-isopropylmalic acid and helps in reduction of aluminum toxicity by forming chelate with Al ions, thereby preventing them from entering the cells.

Application

2-Isopropylmalic acid was employed as an internal standard in diagnostic model for pancreatic cancer using GC/MS-based human serum metabolomics.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Carlo M T Marobbio et al.
The Journal of biological chemistry, 283(42), 28445-28453 (2008-08-07)
In Saccharomyces cerevisiae, alpha-isopropylmalate (alpha-IPM), which is produced in mitochondria, must be exported to the cytosol where it is required for leucine biosynthesis. Recombinant and reconstituted mitochondrial oxalacetate carrier (Oac1p) efficiently transported alpha-IPM in addition to its known substrates oxalacetate
Taisuke Suzuki et al.
Biological trace element research, 120(1-3), 257-263 (2007-10-06)
The budding yeast Saccharomyces cerevisiae secretes 2-isopropylmalic acid (2-iPMA), an intermediate in leucine biosynthesis. Because 2-iPMA binds Al(III) in the culture medium, it is thought to reduce toxicity by Al(III). The effects of 2-iPMA and malic acid (MA) on Al
P S Nielsen et al.
Molecular & general genetics : MGG, 264(5), 613-622 (2001-02-24)
Uptake of branched-chain amino acids by Saccharomyces cerevisiae from media containing a preferred nitrogen source is mediated by the permeases encoded by BAP2, BAP3, and VAP1/TAT1. The transcriptional activity of the BAP2 promoter is affected by a number of genes
J Y Sze et al.
Science (New York, N.Y.), 258(5085), 1143-1145 (1992-11-13)
In the absence of the leucine biosynthetic precursor alpha-isopropylmalate (alpha-IPM), the yeast LEU3 protein (Leu3p) binds DNA and acts as a transcriptional repressor in an in vitro extract. Addition of alpha-IPM resulted in a dramatic increase in Leu3p-dependent transcription. The
P Friden et al.
Molecular and cellular biology, 9(9), 4056-4060 (1989-09-01)
LEU3 of Saccharomyces cerevisiae encodes an 886-amino-acid polypeptide that activates transcription of at least five genes by binding to an upstream decanucleotide sequence. This activation is dependent on the inducer alpha-isopropylmalate, the synthesis of which is repressed by leucine. We
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