O-(N-Succinimidyl)-N,N,N',N'-tetramethyl uronium hexafluoro phosphate (BAT-005707)
* For research use only

Coupling reagent for synthesis of peptide and the formation of other amides.

Category
Fluorinated amino acids
Catalog number
BAT-005707
CAS number
265651-18-1
Molecular Formula
C9H16F6N3O3P
Molecular Weight
359.21
O-(N-Succinimidyl)-N,N,N',N'-tetramethyl uronium hexafluoro phosphate
IUPAC Name
[dimethylamino-(2,5-dioxopyrrolidin-1-yl)oxymethylidene]-dimethylazanium;hexafluorophosphate
Synonyms
N,N,N',N'-Tetramethyl-O-(N-succinimidyl)uronium hexafluorophosphate; HSTU; O-(N-Succinimidyl)-1,1,3,3-tetramethyluronium hexafluorophosphate; AmbotzRL-1039; hexafluorophosphate
Appearance
White to off-white crystalline powder
Purity
≥ 99.5% (HPLC)
Melting Point
218-221 °C
Storage
2-8 °C
Solubility
Soluble in Acetonitrile (0.5 g/mL)
InChI
InChI=1S/C9H16N3O3.F6P/c1-10(2)9(11(3)4)15-12-7(13)5-6-8(12)14;1-7(2,3,4,5)6/h5-6H2,1-4H3;/q+1;-1
InChI Key
STWZCCVNXFLDDD-UHFFFAOYSA-N
Canonical SMILES
CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O.F[P-](F)(F)(F)(F)F
1.Photostable, amino reactive and water-soluble fluorescent labels based on sulfonated rhodamine with a rigidized xanthene fragment.
Boyarskiy VP1, Belov VN, Medda R, Hein B, Bossi M, Hell SW. Chemistry. 2008;14(6):1784-92.
Highly water soluble fluorescent dyes were synthesized and transformed into new amino reactive fluorescent labels for biological microscopy. To this end, rhodamine 8 (prepared from 7-hydroxy-1,2,3,4-tetrahydroquinoline (7) and phthalic anhydride in 85 % aq. H(3)PO(4)) was sulfonated with 30 % SO(3) in H(2)SO(4) and afforded the water soluble disulfonic acid 3 a (64 %). Amidation of the carboxy group in 3 a with 2-(methylamino)ethanol in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluroniumPF(6) (-) (HATU) led to alcohol 3 b (66 %), which was transformed into the amino reactive mixed carbonate 3 d with di(N-succinimidyl)carbonate and Et(3)N. Reaction of the carboxy group in 3 a with MeNH(CH(2))(2)CO(2)Me and N,N,N',N'-tetramethyl-O-(N-succinimidyl)-uroniumBF(4) (-) (TSTU) yielded methyl ester 13. After saponification of the aliphatic carboxy group in 13, the compound was converted into NHS-ester 3 e (using HATU and Et(3)N).
Bio Calculators
Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
g
Quick Inquiry
Verification code
Inquiry Basket