A deuterated form of CEP-lysine
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CEP-Lysine-d4

Item No. 9000595

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(S)-2-amino-6-(2-(2-carboxy-ethyl)-1H-pyrrol-1-yl)-hexanoic-2,2',3,3'-d4-acid
CAS Number
2702446-72-6
Molecular Formula
C13H16D4N2O4
Formula Weight
272.3
Purity
≥99% deuterated forms (d1-d4)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
217 nm
SMILES
OC(C([2H])([2H])C([2H])([2H])C1=CC=CN1CCCC[C@H](N)C(O)=O)=O
InChi Code
InChI=1S/C13H20N2O4/c14-11(13(18)19)5-1-2-8-15-9-3-4-10(15)6-7-12(16)17/h3-4,9,11H,1-2,5-8,14H2,(H,16,17)(H,18,19)/t11-/m0/s1/i6D2,7D2
InChi Key
GUYNPRDOGAXJKQ-YUQOGSRCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $250

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    1 mg

    $472

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    Product Description

    CEP-Lysine-d4 contains four deuterium atoms at the carboxyethyl 2,3',3,3' positions. It is intended for use as an internal standard for the quantification of CEP-lysine by GC- or LC-mass spectrometry (MS). Docosahexaenoic acid (DHA) is an ω-3 polyunsaturated fatty acid that is abundant in the brain and in photoreceptor cell membranes in the retina. Oxidative cleavage of phospholipids containing DHA produces reactive electophilic phospholipid fragments, including 4-hydroxy-7-oxohept-5-enoates.1 These can interact with the primary amine group of lysyl residues to produce 2-(ω-carboxyethyl)pyrrole (CEP) derivatives, which are abundant in certain diseases.2,3 Advanced glycation end products, including CEP-lysine are biomarkers for age-related macular degeneration.4,5 CEP-lysine-d4 is a deuterated form of CEP-lysine.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lu, L., Gu, X., Hong, L., et al. Synthesis and structural characterization of carboxyethylpyrrole-modified proteins: Mediators of age-related macular degeneration. Bioorg. Med. Chem. 17(21), 7548-7561 (2009).

    2. Gu, X., Sun, M., Gugiu, B., et al. Oxidatively truncated docosahexaenoate phospholipids: Total synthesis, generation, and peptide adduction chemistry. The Journal of Organic Chemistry 68(10), 3749-3761 (2003).

    3. Crabb, J.W., Miyagi, M., Gu, X., et al. Drusen proteome analysis: An approach to the etiology of age-related macular degeneration. Proc. Natl. Acad. Sci. USA 99(23), 14682-14687 (2002).

    4. Gu, J., Pauer, G.J.T., Yue, X., et al. Assessing susceptibility to age-related macular degeneration with proteomic and genomic biomarkers. Mol. Cell. Proteomics 8(6), 1338-1349 (2009).

    5. Ni, J., Yuan, X., Gu, J., et al. Plasma protein pentosidine and carboxymethyllysine, biomarkers for age-related macular degeneration. Mol. Cell. Proteomics 8(8), 1921-1933 (2009).