94790-37-1 Usage
Uses
Used in Pharmaceutical Industry:
HBTU is used as a peptide coupling reagent for the synthesis of peptides and proteins. Its ability to reduce racemization makes it a preferred choice in the development of therapeutic peptides and protein-based drugs, ensuring the production of high-quality and biologically active compounds.
Used in Research and Development:
In academic and industrial research settings, HBTU is utilized as a key component in the synthesis of complex peptide sequences and the development of novel peptide-based therapeutics. Its efficiency in promoting peptide bond formation and minimizing racemization contributes to the advancement of peptide science and drug discovery.
Used in Chemical Synthesis:
Beyond its applications in peptide synthesis, HBTU is also employed as a general coupling reagent in various chemical reactions. Its versatility allows it to be used in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Biological Activity
hbtu (2-(1h-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexauorophosphate), a coupling reagent commonly used in solid phase peptide synthesis. after being introduced in 1978, this agent shows popularity in chemistry and industry use due to its mild activating properties. moreover, it also shows resistance against racemization. low tendency for racemization is a key requirement for peptide synthesis. especially for solid phase peptide synthesis, quantitative yields with short reaction times are crucial in order to make the synthesis of large peptides feasible. [1]
in vitro
peptide synthesis relied mostly on efficient and safe coupling reagents. hbtu was proved to transform carboxylic acids into azides efficiently and practically. the process might be applied to a wide range of carboxylic acids including n-protected amino acids. in addition, hbtu was of great value in one-pot synthesis of dipeptidyl urea esters, ureas, and carbamates from acids. the advantages of hbtu included the following points: 1) non-explosive and therefore more suitable for solution/solid phase peptide synthesis. 2) high solubility and stability in classical solvents. 3) feasible for colorimetric reaction monitoring. [2]
Purification Methods
Wash the salt with H2O (3x), CH2Cl2 (3x), dry and recrystallise it from MeCN. Dry it in a vacuum and store it cold in the dark [Dourtoglou et al. Tetrahedron Lett 1269 1978, NMR: Dourtoglou and Gross Synthesis 572 1984]. Benzoxazolinone (2 -hydroxybenzoxazole) [59 -49 -4] M 135.1, m 137 -139o, 142 -143o(corrected), b 121-213o/17mm, 335-337o/760mm. Benzoxazolinone is purified by recrystallisation from aqueous Me2CO followed by distillation at atmospheric pressure, then in a vacuum. The methyl mercury salt recrystallises from aqueous EtOH and has m 156-158o. [Bywater et al. J Am Chem Soc 67 905 1945, Beilstein 27 III/IV 2677.]
references
[1]adam s. hbtu: a mild activating ageiw of muramic acid. bioorg med chem lett. 1992 mar; 2(6): 571-4.[2]knorr r, trzeciak a, bannwarth w and gillessen d. new coupling reagents in peptide chemistry. tetrahedron lett. 1989; 30(15): 1927-30.
Check Digit Verification of cas no
The CAS Registry Mumber 94790-37-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,4,7,9 and 0 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 94790-37:
(7*9)+(6*4)+(5*7)+(4*9)+(3*0)+(2*3)+(1*7)=171
171 % 10 = 1
So 94790-37-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H16N5O.F6P/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;1-7(2,3,4,5)6/h5-8H,1-4H3;/q+1;-1
94790-37-1Relevant articles and documents
Radiofluorination methods
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, (2008/12/08)
The present invention relates to radiolabelled substitute benzene compounds for diagnostic imaging. The present invention provides methods for preparation of such compounds, in particular, preparation of novel compounds which serve as precursors for 18F-labeling, and the use of thus 18F-labeled compounds for diagnostic imaging.
Method of forming N-protected amino acid thiohydantoins
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, (2008/06/13)
A method of forming a thiohydantoin from an N-protected amino acid. The method employs a uronium or phosphonium compound to activate the terminal carboxyl group of the amino acid and a thiocyanate reagent to cyclize the activated amino acid to the thio-hydantoin. The thiohydantoin can be cleaved from its N-protecting group, for use in C-terminal peptide sequencing. Particularly preferred uronium compounds include salts of 2-chlorouronium. Preferred thiocyanate reagents include trimethylsilyl isothiocyanate and crown ether adducts of metallothiocyanates, such as the 18-crown-6 adduct of KSCN.
NEW COUPLING REAGENTS IN PEPTIDE CHEMISTRY
Knorr, Reinhard,Trzeciak, Arnold,Bannwarth, Willi,Gillessen, Dieter
, p. 1927 - 1930 (2007/10/02)
2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) has been applied as coupling reagent to solid phase peptide synthesis.Furthermore, a general synthetic procedure for new derivatives of different N-hydroxy compounds has been developed.They either act as excellent activating reagents causing low racemization during condensation of peptide segments or are useful tools for the formation of active esters suitable for couplings in mixed aqueous / organic media, respectively.
