82911-69-1 Usage
Description
N-(9-Fluorenylmethoxycarbonyloxy)succinimide, commonly known as Fmoc-OSu, is a versatile reagent used in organic synthesis and biochemistry. It is a white powder that serves as a protecting group and activating agent in the synthesis of oligonucleotides and peptides. Fmoc-OSu is particularly useful for the preparation of pure Fmoc amino acids, ensuring they are free from contamination by Fmoc-dipeptides. Its ability to facilitate partial Edman degradation in conjunction with isothiocyanate makes it a valuable tool in the study and analysis of biologically active peptides.
Uses
Used in Peptide and Oligonucleotide Synthesis:
Fmoc-OSu is used as a protecting and activating reagent for the synthesis of oligonucleotides and peptides. It aids in the stepwise addition of amino acids or nucleotides, enabling the controlled and efficient construction of these biologically significant molecules.
Used in Pharmaceutical and Biochemical Research:
In the pharmaceutical and biochemical research industries, Fmoc-OSu is used as a reagent for the preparation of pure Fmoc amino acids. This ensures that the amino acids are free from contamination by Fmoc-dipeptides, which is crucial for the accuracy and reliability of experimental results.
Used in Protein Sequencing:
Fmoc-OSu is used in conjunction with isothiocyanate to conduct partial Edman degradation on biologically active peptides. This technique is vital for determining the amino acid sequence of proteins, which is essential for understanding their structure, function, and potential applications in medicine and biotechnology.
Chemical Properties:
Fmoc-OSu is a white powder with specific chemical properties that make it suitable for use as a protecting and activating reagent in various biochemical applications. Its physical form and reactivity contribute to its effectiveness and ease of use in laboratory settings.
Purification Methods
Recrystallise the carbonate from CHCl3/Et2O, or from pet ether (b 40-60o). [Pauet Can J Chem 60 976 1982, Lapatsaris et al. Synthesis 671 1983.]
Check Digit Verification of cas no
The CAS Registry Mumber 82911-69-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,9,1 and 1 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 82911-69:
(7*8)+(6*2)+(5*9)+(4*1)+(3*1)+(2*6)+(1*9)=141
141 % 10 = 1
So 82911-69-1 is a valid CAS Registry Number.
InChI:InChI=1/C19H15NO5/c21-17-9-10-18(22)20(17)25-19(23)24-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2
82911-69-1Relevant articles and documents
Method for synthesizing 9-fluorenylmethylsuccinimido carbonate by one-pot two-phase method
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Paragraph 0011; 0024-0029, (2020/03/03)
The invention relates to the technical field of organic synthesis, specifically to a method for synthesizing 9-fluorenylmethylsuccinimido carbonate by a one-pot two-phase method. The method comprisesthe following steps: adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid caustic soda under stirring, after the liquid caustic soda is dropwise added, adding butanedioic anhydride in batches, and carrying out high-temperature vacuum dehydration under acid catalysis until no water is extracted out so as to prepare an N-hydroxysuccinimide solution; adding a chloroformic acid-9-fluorenyl methyl ester solution into the N-hydroxysuccinimide solution, and controlling a temperature at 0 to 60 DEG C; after the chloroformic acid-9-fluorenyl methyl ester solution is added, starting to dropwise add an aqueous alkali solution; after the aqueous alkali solution is dropwise added, separating out an organic layer, carrying out concentrating to dryness, and carrying out recrystallizing so as to obtain a 9-fluorenylmethylsuccinimido carbonate finished product. The above-mentioned method provided by the invention innovatively adopts the one-pot two-phase method; a reaction liquid containing N-hydroxysuccinimide is directly used for synthesizing the 9-fluorenylmethylsuccinimido carbonate in a two-phase reaction manner; process steps are effectively reduced; and the method is applicable to large-scale industrial production.
The two pathways for effective orthogonal protection of L-ornithine, for amino acylation of 5'-O-Pivaloyl nucleosides, describe the general and important role for the successful imitation, during the synthesis of the model substrates for the ribosomal mimic reaction
Bayryamov, Stanislav G.,Vassilev, Nikolay G.,Petkov, Dimiter D.
experimental part, p. 889 - 898 (2011/12/14)
Bz(NO2)-Orn(Boc)-OCH2CN was synthesized as an amino acid component with effective and successful orthogonal protection for amino acylation of 5'-O-Pivaloyl nucleosides and preparation of substrates for model ribosome reactions. The synthesis was carried out using suitable combinations of the methods of peptide synthesis and modification of amino acids.
Scalable synthesis of Nα-benzyloxycarbonyl-L-ornithine and of Nα-(9-fluorenylmethoxy)carbonyl-L-ornithine
Masiukiewicz, Elzbieta,Wiejak, Stanislaw,Rzeszotarska, Barbara
, p. 531 - 537 (2007/10/03)
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