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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
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Quality Level

100

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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Show Differences

1 of 4

This Item
SAB1300288HPA031151SAE0093
Sigma-Aldrich

44498

β-1,4-Galactosyl Transferase I human, recombinant from Saccharomyces cerevisiae

Anti-GCNT1 (center) antibody produced in rabbit IgG fraction of antiserum, buffered aqueous solution

SAB1300288

Anti-GCNT1 (center) antibody produced in rabbit

Anti-GCNT1 antibody produced in rabbit Prestige Antibodies® Powered by Atlas Antibodies, affinity isolated antibody, buffered aqueous glycerol solution

HPA031151

Anti-GCNT1 antibody produced in rabbit

Beta-1,4-galactosyltransferase 1 B4GALT1 human recombinant, expressed in HEK 293 cells, 2000 units/mg protein

SAE0093

Beta-1,4-galactosyltransferase 1

Gene Information

human ... GCNT1(2650)

Gene Information

human ... GCNT1(2650)

Gene Information

human ... GCNT1(2650)

Gene Information

-

recombinant

expressed in Saccharomyces cerevisiae

recombinant

-

recombinant

-

recombinant

expressed in HEK 293 cells

concentration

≥0.2 unit/mL, 0.5-4 mg/mL protein

concentration

-

concentration

-

concentration

-

UniProt accession no.

Q02742

UniProt accession no.

Q02742

UniProt accession no.

Q02742

UniProt accession no.

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

impurities

≤0.1% β-galactosidase

impurities

-

impurities

-

impurities

-

General description

2-Isopropylmalic acid is an intermediate formed during leucine biosynthesis.[1] 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.[2]

Application

2-Isopropylmalic acid was employed as an internal standard in diagnostic model for pancreatic cancer using GC/MS-based human serum metabolomics.[3]

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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    MKBZ2967V
    04027AE
    12127BO
    04721KN
    04009DY

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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
    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
    Satoshi Takemoto et al.
    Animal science journal = Nihon chikusan Gakkaiho, 88(12), 1970-1978 (2017-07-20)
    Long-distance transportation is sometimes inevitable in the beef industry because of the geographic separation of major breeding and fattening areas. Long-distance transportation negatively impacts production and health of cattle, which may, at least partly, result from the disturbance of metabolism
    View All Related Papers

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