Introduction：Basic information about Fmoc-OSu CAS 82911-69-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Fmoc-OSu Basic information
| Product Name: | Fmoc-OSu |
| Synonyms: | 1-[[(9h-fluoren-9-ylmethoxy)carbonyl]oxy]-5-pyrrolidinedione;9-fluorenylmethoxycarbonyloxysuccinimide;9-fluorenylmethyl-n-succinimide carbonate;N-(9-FluorenylmethoxyCarbonyloxy)Succinimide9-Fluorenylmethylsuccinimidylcarbonate;CARBONIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTER 9H-FLUOREN-9-YLMETHYL ESTER;CARBONIC ACID FLUORENYLMETHYL SUCCIN-N-YL-ESTER;FMOC-OSU;FMOC-ONSU |
| CAS: | 82911-69-1 |
| MF: | C19H15NO5 |
| MW: | 337.33 |
| EINECS: | 433-520-5 |
| Product Categories: | Fmoc-OSU;peptides;Medical Intermediates;Fluorenes, Flurenones;Benzocycles;Pyrrolidines;N-Protecting Reagents;Amino Acid Derivatives;Heterocycles;Miscellaneous Reagents;Biochemistry;Condensation & Active Esterification;Fluorenes;Fluorenes & Fluorenones;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Peptide Synthesis;Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry;Fmoc-Amino acid series;bc0001 |
| Mol File: | 82911-69-1.mol |
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Fmoc-OSu Chemical Properties
| Melting point | 150-153 °C(lit.) |
| Boiling point | 150-153°C |
| density | 1.3460 (rough estimate) |
| refractive index | 1.5000 (estimate) |
| storage temp. | 2-8°C |
| solubility | Soluble in dimethyl sulfoxide and dimethyl formamide. |
| form | Microfine Powder |
| color | White or almost white |
| Sensitive | Moisture Sensitive |
| BRN | 3569540 |
| Stability: | Moisture Sensitive |
| Major Application | peptide synthesis |
| InChI | InChI=1S/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 |
| InChIKey | WMSUFWLPZLCIHP-UHFFFAOYSA-N |
| SMILES | C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)(=O)ON1C(=O)CCC1=O |
| CAS DataBase Reference | 82911-69-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,N,Xn |
| Risk Statements | 36/37/38-51/53-43-22 |
| Safety Statements | 22-24/25-26/37/39-26-61-37-24 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| F | 10-21 |
| Hazard Note | Moisture Sensitive |
| HazardClass | 9 |
| HS Code | 29251995 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral
Aquatic Chronic 2
Skin Sens. 1 |
Fmoc-OSu Usage And Synthesis
| Description | Fmoc-OSu (N-(9-Fluorenylmethoxycarbonyloxy)succinimide) is a reagent used in solid-phase peptide synthesis (SPPS) for Fmoc protection of amino groups, particularly amino acids. This reagent contains an Fmoc functional group, which is stable under acidic conditions and cleaves under alkaline conditions. Fmoc-OSu reacts with amino groups to form stable amide bonds, helping to reduce the occurrence of side reactions. Additionally, Fmoc-OSu can also be used as a fluorescent reagent. |
| Chemical Properties | White powder |
| Uses | N-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides. |
| Uses | N-protecting reagent for oligonucleotide and peptide syntheses |
| Uses | Reagent for the preparation of pure Fmoc amino acids free from contamination by Fmoc-dipeptides. |
| Mechanism of action | The protective mechanism of Fmoc-OSu involves the amine group (R-NH₂) of the protected molecule acting as a nucleophile and attacking the carbonyl carbon of the Fmoc-OSu molecule, forming a tetrahedral intermediate. where the nitrogen of the amine is now bonded to the carbonyl carbon of the Fmoc group, yielding an Fmoc-protected amine and a succinimide. The Fmoc group is typically removed using bases such as piperidine, which can remove the Fmoc group without hydrolyzing the peptide backbone. In solid-phase peptide synthesis (SPPS), the removal of the Fmoc group occurs via a two-step mechanism: first, the acidic proton at the 9-position of the naphthalene ring system is removed using a mild base (preferably a secondary amine), followed by a β-elimination reaction, generating a highly reactive dibenzofuran (DBF) intermediate, which is immediately captured by the secondary amine to form a stable adduct.
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| 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.] |
Fmoc-OSu Preparation Products And Raw materials
| Preparation Products | Fmoc-8-amino-3,6-dioxaoctanoic acid-->FMOC-L-PROPARGYLGLYCINE-->FMOC-b-Ala-OH-->Fmoc-Leu-OH-->FMOC-D-PHG-OH-->Fmoc-L-4-Iodophenylalanine-->Fmoc-4-nitro-L-phenylalanine-->FMOC-L-Arginine-->Fmoc-Cys(tBu)-OH-->N-Boc-N'-Fmoc-L-Lysine-->Fmoc-L-hydroxyproline-->FMOC-(2S,3R)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID-->Piperidine, 1-(9H-fluoren-9-ylmethyl)--->FMOC-2-(2-AMINOETHOXY)ETHANOL-->N-Fmoc-L-homoserine-->Nalpha-FMOC-L-Tryptophan-->FMOC-L-Methionine |
