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I7634

Sigma-Aldrich

D-Isoleucine

≥98% (TLC)

Synonym(s):

(2R, 3R)-2-Amino-3-methylpentanoic acid

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About This Item

Linear Formula:
C2H5CH(CH3)CH(NH2)CO2H
CAS Number:
319-78-8
Molecular Weight:
131.17
EC Number:
206-269-2
MDL number:
MFCD00064221
UNSPSC Code:
12352209
PubChem Substance ID:
24896122
NACRES:
NA.26

product name

D-Isoleucine, ≥98% (TLC)

Quality Level

200

Assay

≥98% (TLC)

form

powder

impurities

≤10% allo-isomer

color

white

application(s)

cell analysis

SMILES string

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

InChI

1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m1/s1

InChI key

AGPKZVBTJJNPAG-RFZPGFLSSA-N

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Application


  • Metabolic Profiling of Urinary Chiral Amino-Containing Biomarkers for Gastric Cancer Using a Sensitive Chiral Chlorine-Labeled Probe by HPLC-MS/MS.: This study by Huang et al. (2021) explores the use of D-Isoleucine as a biomarker for gastric cancer, utilizing advanced metabolic profiling techniques with HPLC-MS/MS to detect chiral amino-containing compounds in urine samples (Huang et al., 2021).

  • Isopenicillin N Synthase Binds δ-(L-α-aminoadipoyl)-L-cysteinyl-D-thia-allo-isoleucine Through Both Sulfur Atoms.: Clifton et al. (2011) describe the binding mechanism of Isopenicillin N synthase with a compound involving D-Isoleucine, highlighting its role in antibiotic biosynthesis and enzyme interaction studies (Clifton et al., 2011).

  • The Total Structure of the Antibiotic Longicatenamycin.: Shiba and Mukunoki (1975) determined the complete structure of the antibiotic longicatenamycin, which includes D-Isoleucine as a crucial component, contributing to understanding its antibacterial properties (Shiba and Mukunoki, 1975).

Biochem/physiol Actions

D-Isoleucine may be used to help characterize and differentiate various D-amino acid oxidases. D-Isoleucine may be used to differentiate the activities of D- and L-isoleucine in processes such as the induction of pigmentation in B16F0 melanoma cells.

Storage Class Code

11 - Combustible Solids

WGK

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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A Gholizadeh et al.
Biochemistry. Biokhimiia, 74(2), 137-144 (2009-03-10)
D-Amino acid oxidase (DAAO) is an FAD-dependent enzyme that metabolizes D-amino acids in microbes and animals. However, such ability has not been identified in plants so far. We predicted a complete DAAO coding sequence consisting of 1158 bp and encoding
Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic D- and L-amino acids. IV. The L-phenylalanine series.
Gorbitz CH, Rissanen K, Valkonen A, Husab? A.
Acta Crystallographica Section C, Crystal Structure Communications, 65, 267-272 (2009)
Masago Ishikawa et al.
Biological & pharmaceutical bulletin, 30(4), 677-681 (2007-04-06)
Amino acids, the building blocks of proteins, play significant roles in numerous physiological events in mammals. As the effects of amino acids on melanogenesis have yet to be demonstrated, the present study was conducted to identify whether amino acids, in
Shouji Takahashi et al.
Journal of biochemistry, 159(3), 371-378 (2015-11-01)
D-Aspartate oxidase (DDO) catalyzes the oxidative deamination of acidic D-amino acids, whereas neutral and basic D-amino acids are substrates of D-amino acid oxidase (DAO). DDO of the yeast Cryptococcus humicola (ChDDO) has much higher substrate specificity to D-aspartate, but the
Ivan Kashkan et al.
Plants (Basel, Switzerland), 9(7) (2020-07-12)
Rapid progress in plant molecular biology in recent years has uncovered the main players in hormonal pathways and characterized transcriptomic networks associated with hormonal response. However, the role of RNA processing, in particular alternative splicing (AS), remains largely unexplored. Here
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Chromatograms

application for HPLC

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