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L-(7-hydroxycoumarin-4-yl)ethylglycine

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Catalog: ASIS-0105

Formal Name: L-(7-hydroxycoumarin-4-yl)ethylglycine

Produced By: AsisChem, Inc.

Related Files
pdfASIS-0105 Technical Product Information (506.88 KB )
pdfASIS-0105 Safety Data Sheet (92.69 KB )

Biological Description

L-(7-hydroxycoumarin-4-yl)ethylglycine (7-HC), ASIS-0105, is a genetically encodable unnatural amino acid (UAA) which has a high fluorescence quantum yield and a large Stoke’s shift in response to pH and solvent polarity (Wang, Xie et al. 2006, Lacey, Parrish et al. 2011, Chen, Fahmi et al. 2013). The ability to incorporate 7-HC at a specific residue allows for analysis of environmental influences on protein structure and behavior. Site specific incorporation of 7-HC relies upon an orthangonal tRNA and amino acyl tRNA synthetase derived from Methanococcus jannaschii amber suppressor tyrosyl-tRNA (MjtRNATyr CUA/tyrosyl-tRNA synthestase (MjTyrRS). Plasmids containing these sequences have been published and previous studies report the use of 1mM 7-HC for incorporation steps with one study reporting a much as 2 mg/L of target protein (Wang, Xie et al. 2006, Lacey, Parrish et al. 2011).
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Additional Information

Quantities Please contact us for larger or different quantities
Catalog ASIS-0105
Formal Name L-(7-hydroxycoumarin-4-yl)ethylglycine
Weight (mg & g) No
CAS Number none
Molecular Weight 263.246032714844
Formula C13 H13 N O5
Lead Time 3
LogP 1.543400049
Purity 95
SMILES C1=C(CC[C@@H](C(O)=O)N)C2C=CC(O)=CC=2OC1=O |&1:4|
Solubility and Handling Room temperature
inchikey QEQAKQQRJFWPOR-JTQLQIEISA-N
TPSA 113.7600021
HBD 3
HBA 6

Details

Chen, S., N. E. Fahmi, L. Wang, C. Bhattacharya, S. J. Benkovic and S. M. Hecht (2013). "Detection of dihydrofolate reductase conformational change by FRET using two fluorescent amino acids." J Am Chem Soc 135(35): 12924-12927 (http://www.ncbi.nlm.nih.gov/pubmed/23941571).(Abstract)

Lacey, V. K., A. R. Parrish, S. Han, Z. Shen, S. P. Briggs, Y. Ma and L. Wang (2011). "A fluorescent reporter of the phosphorylation status of the substrate protein STAT3." Angew Chem Int Ed Engl 50(37): 8692-8696 (http://www.ncbi.nlm.nih.gov/pubmed/21805546).(Abstract)

Wang, Q., A. R. Parrish and L. Wang (2009). "Expanding the genetic code for biological studies." Chem Biol 16(3): 323-336 (http://www.ncbi.nlm.nih.gov/pubmed/19318213).(Abstract)

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Product Details

Additional Information

Quantities Please contact us for larger or different quantities
Catalog ASIS-0105
Formal Name L-(7-hydroxycoumarin-4-yl)ethylglycine
Weight (mg & g) No
CAS Number none
Molecular Weight 263.246032714844
Formula C13 H13 N O5
Lead Time 3
LogP 1.543400049
Purity 95
SMILES C1=C(CC[C@@H](C(O)=O)N)C2C=CC(O)=CC=2OC1=O |&1:4|
Solubility and Handling Room temperature
inchikey QEQAKQQRJFWPOR-JTQLQIEISA-N
TPSA 113.7600021
HBD 3
HBA 6
References

Details

Chen, S., N. E. Fahmi, L. Wang, C. Bhattacharya, S. J. Benkovic and S. M. Hecht (2013). "Detection of dihydrofolate reductase conformational change by FRET using two fluorescent amino acids." J Am Chem Soc 135(35): 12924-12927 (http://www.ncbi.nlm.nih.gov/pubmed/23941571).(Abstract)

Lacey, V. K., A. R. Parrish, S. Han, Z. Shen, S. P. Briggs, Y. Ma and L. Wang (2011). "A fluorescent reporter of the phosphorylation status of the substrate protein STAT3." Angew Chem Int Ed Engl 50(37): 8692-8696 (http://www.ncbi.nlm.nih.gov/pubmed/21805546).(Abstract)

Wang, Q., A. R. Parrish and L. Wang (2009). "Expanding the genetic code for biological studies." Chem Biol 16(3): 323-336 (http://www.ncbi.nlm.nih.gov/pubmed/19318213).(Abstract)

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