333115
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:
Molecular Weight:
176.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
mp
144-146 °C (lit.)
functional group
carboxylic acid
hydroxyl
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 Code
11 - 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
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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
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
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