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R,S-(2,2'-Bipyridin-5-yl)alanine

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Catalog: ASIS-0021

Formal Name: (R,S)-3-([2,2'-bipyridin]-5-yl)-2-aminopropanoic acid dihydrochloride

Produced By: AsisChem, Inc.

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pdfASIS-0021_Technical_Product_Information (524.82 KB )
pdfASIS-0021 SDS.pdf (93.03 KB )

Biological Description

BpyAla, ASIS-0021, is a genetically encodable metal-binding unnatural amino acid (UAA) with utility in protein engineering and functional studies (Xie, Liu et al. 2007, Lee, Spraggon et al. 2009, Drienovska, Rioz-Martinez et al. 2015). Bpy-Ala has been shown to strongly chelate transition metal ions including Fe2+, Fe3+, Cu2+, Ru2+, Ru3+, Co2+, and Co3+(Xie, Liu et al. 2007). Additionally, Bpy-Ala is able to form multimeric metal ion structures and can be used to synthetically direct conjugation and protein-protein interactions.
Site specific incorporation of BpyAla relies upon an orthogonal tRNA and amino acyl tRNA synthetase derived from a Methanococcus jannaschii amber suppressor tyrosyl-tRNA (MjtRNATyr CUA/tyrosyl-tRNA synthestase (MjTyrRS)(Xie, Liu et al. 2007). Previous studies have used 0.2 µM-1.0 µM of BpyAla in media with BL21(DE3) or DH10? cells for incorporation of BpyAla into proteins at an engineered TAG codon (Xie, Liu et al. 2007, Lee, Spraggon et al. 2009, Drienovska, Rioz-Martinez et al. 2015).

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Additional Information

Quantities Please contact us for larger or different quantities
Catalog ASIS-0021
Formal Name (R,S)-3-([2,2'-bipyridin]-5-yl)-2-aminopropanoic acid dihydrochloride
CAS Number 146581-79-5 (for S)
Molecular Weight 316.18310546875
Formula C13 H15 Cl2 N3 O2
Lead Time 1
LogP 4.2
Purity 95
SMILES Cl.Cl.NC(C(O)=O)CC1C=NC(C2N=CC=CC=2)=CC=1
Solubility and Handling No
inchikey CSMZEFIPOKQUIS-UHFFFAOYSA-N
TPSA 89.1
HBD 5
HBA 5

Details

Drienovska, I., A. Rioz-Martinez, A. Draksharapu and G. Roelfes (2015). "Novel artificial metalloenzymes by in vivo incorporation of metal-binding unnatural amino acids." Chemical Science 6(1): 770-776(Abstract)

Lee, H. S., G. Spraggon, P. G. Schultz and F. Wang (2009). "Genetic incorporation of a metal-ion chelating amino acid into proteins as a biophysical probe." J Am Chem Soc 131(7): 2481-2483(Abstract)

Wang, Q., A. R. Parrish and L. Wang (2009). "Expanding the genetic code for biological studies." Chem Biol 16(3): 323-336(Abstract)

Xie, J., W. Liu and P. G. Schultz (2007). "A genetically encoded bidentate, metal-binding amino acid." Angew Chem Int Ed Engl 46(48): 9239-9242(Abstract)

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Product Details

Additional Information

Quantities Please contact us for larger or different quantities
Catalog ASIS-0021
Formal Name (R,S)-3-([2,2'-bipyridin]-5-yl)-2-aminopropanoic acid dihydrochloride
CAS Number 146581-79-5 (for S)
Molecular Weight 316.18310546875
Formula C13 H15 Cl2 N3 O2
Lead Time 1
LogP 4.2
Purity 95
SMILES Cl.Cl.NC(C(O)=O)CC1C=NC(C2N=CC=CC=2)=CC=1
Solubility and Handling No
inchikey CSMZEFIPOKQUIS-UHFFFAOYSA-N
TPSA 89.1
HBD 5
HBA 5
References

Details

Drienovska, I., A. Rioz-Martinez, A. Draksharapu and G. Roelfes (2015). "Novel artificial metalloenzymes by in vivo incorporation of metal-binding unnatural amino acids." Chemical Science 6(1): 770-776(Abstract)

Lee, H. S., G. Spraggon, P. G. Schultz and F. Wang (2009). "Genetic incorporation of a metal-ion chelating amino acid into proteins as a biophysical probe." J Am Chem Soc 131(7): 2481-2483(Abstract)

Wang, Q., A. R. Parrish and L. Wang (2009). "Expanding the genetic code for biological studies." Chem Biol 16(3): 323-336(Abstract)

Xie, J., W. Liu and P. G. Schultz (2007). "A genetically encoded bidentate, metal-binding amino acid." Angew Chem Int Ed Engl 46(48): 9239-9242(Abstract)

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