CEP-Lysine-d₄ Exclusive

Cayman Chemical Item Number 9000595

CEP-Lysine-d4

See more	Mass Spectrometry (265) Analytical Standards (150) Oxidative Injury (291)

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.(18413,18415} CEP-lysine-d₄ is a deuterated form of CEP-lysine.

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 7548-7561 (2009).

2 Gu, X., Sun, M., Gugiu, B., et al. Oxidatively truncated docosahexaenoate phospholipids: Total synthesis, generation, and peptide adduction chemistry. J Org Chem 68 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).

Formal Name	(S)-2-amino-6-(2-(2-carboxy-ethyl)-1H-pyrrol-1-yl)-hexanoic-2,2',3,3'-d4-acid
Molecular Formula	C₁₃H₁₆D₄N₂O₄
Formula Weight	272.3
Formulation	A crystalline solid
Purity	≥99% deuterated forms (d1-d4)
λ_max	217 nm
Stability	2 years
Storage	-20°C
Shipping	Wet ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard OC(C([2H])([2H])C([2H])([2H])C1=CC=CN1CCCC[C@H](N)C(O)=O)=O

Background Reading

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 7548-7561 (2009).

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

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).

Gu, X., Sun, M., Gugiu, B., et al. Oxidatively truncated docosahexaenoate phospholipids: Total synthesis, generation, and peptide adduction chemistry. J Org Chem 68 3749-3761 (2003).

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 1338-1349 (2009).

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Size	Global Purchasing
500 µg	See a distributor in your region for pricing
1 mg	See a distributor in your region for pricing
5 mg	See a distributor in your region for pricing
10 mg	See a distributor in your region for pricing

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Batch-specific Information

FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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CEP-Lysine-d4 Exclusive