L511382
4-Formylbenzene diazonium hexafluorophosphate
AldrichCPR
Synonym(s):
FBDP
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About This Item
Empirical Formula (Hill Notation):
C7H5F6N2OP
Molecular Weight:
278.09
UNSPSC Code:
12352200
PubChem Substance ID:
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SMILES string
[F-].FP(F)(F)(F)F.O=Cc1ccc(cc1)[N+]#N
InChI
1S/C7H5N2O.F5P.FH/c8-9-7-3-1-6(5-10)2-4-7;1-6(2,3,4)5;/h1-5H;;1H/q+1;;/p-1
InChI key
FIPGAZNYTIMGRF-UHFFFAOYSA-M
Application
- Tyrosine-selective bioconjugation reagent for the incorporation of a bioorthogonal aldehyde into peptides, proteins, antibodies or cell surfaces.[1]
- The aldehyde can then be reacted with a variety of bioconjugation, labeling or detection reagents containing hydrazine/hydrazide or oxyamine functionalities.[1]
- FBDP is a novel development in the field of Tyr bioconjugation as it is bench-stable as opposed to prevoius diazonium reagents that require in situ preparation.[1]
- FBDP has been shown to modify small molecules, peptides, proteins and living cell surface proteins in high yields.[1]
- The labeling proceeds quickly with common reaction times of 30 min at room temperature at pH 7-8 (slightly higher yield and selectivity seen at pH 8).[1]
Reference: Formylbenzene Diazonium Hexafluorophosphate Reagent for Tyrosine-selective Modification of Proteins and the Introduction of a Bioorthogonal Aldehyde Gavrilyuk, J.; Ban, H.; Nagano, M.; Hakamata, W.; Barbas III, C.F. Bioconjugate Chemistry (2012) 23: 2321-2328 DOI: 10.1021/bc300410p
Other Notes
Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.
NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.
NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Julia Gavrilyuk et al.
Bioconjugate chemistry, 23(12), 2321-2328 (2012-11-28)
4-Formylbenzene diazonium hexafluorophosphate (FBDP) is a novel bench-stable crystalline diazonium salt that reacts selectively with tyrosine to install a bioorthogonal aldehyde functionality. Model studies with N-acyl-tyrosine methylamide allowed us to identify conditions optimal for tyrosine ligation reactions with small peptides
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