N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine
N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine is an unnatural lysine analog and a substrate of the PABKRS mutant PylRS. N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine enables site-specific genetic integration into proteins via amber stop codon suppression; it undergoes Staudinger reduction with phosphine compounds, followed by a self-elimination reaction to release native lysine. N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine serves as a genetically encoded element for the temporal chemical control of protein SUMOylation and nuclear translocation in living mammalian cells, and also acts as a bioorthogonal reaction handle for bioconjugation reactions.
For research use only. We do not sell to patients.
- CAS No.: 1513855-74-7
- Formula: C14H19N5O4
- Molecular Weight:321.33
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
Biological Activity
Description
In Vitro
H‑L‑Lys (4‑N3‑Z)‑OH (PABK) hydrochloride exhibits a deprotection reaction with a t95 of 17.7 min[1].
N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine is efficiently incorporated into sfGFP-Y151TAG to yield unmodified sfGFP-Y151PABK in Escherichia coli expressing the PABKRS synthetase[1].
N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine is efficiently incorporated into the mCherry-TAG-EGFP-HA reporter gene in transfected HEK293T cells to produce full-length fusion proteins at high yields[1].
N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine mediates phosphine-triggered nuclear translocation, with a t1/2 of 26.7 min in the presence of 100 μM 2DPBM (complete translocation is achieved at 75 min)[1].
N6-[[(4-Azidophenyl)methoxy]carbonyl]-L-lysine enables the quantitative conversion of unmodified RGΔN to its 37 kDa SUMOylated form via the endogenous cellular SUMOylation pathway through a phosphine-triggered deprotection reaction in HEK293T cells expressing FLAG-RGΔN-K526TAG[1].
H‑L‑Lys (4‑N3‑Z)‑OH hydrochloride enables phosphine‑mediated activation of RanGAP1‑K524PABK‑RFP and restores native SUMOylation[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 1513855-74-7
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Molecular Weight 321.33
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Formula C14H19N5O4
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SMILES
N[C@@H](CCCCNC(OCC1=CC=C(N=[N+]=[N-])C=C1)=O)C(O)=O
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)